organic c cccc cccc

7/24/2019 Organic c Cccc Cccc

1/88

Catholic Junior CollegeH2 Chemistry 9647

ContentsPage

1. Arenes. 1

2. Reaction Kinetics. 9

3. Halogen Derivatives.. 224. Hydroxy Componds

. 31!. Car"onyl Componds

4#

#. Car"oxylic Acids $ Derivatives.. #3

%. &itrogen Componds.. '(

'. )rop **

.. 99

2014 JC2 MYE Toical!e"ision Pac#age 1


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Arenes

QUESTIONS

Name: _________________________________________

Class: 2T____


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1$ %renes

Arenes

1. Which of the following sequences of bromination, nitration and oxidation is exected to gi!e thebest "ield for s"nthesis of 2#bromo#$#nitroben%oic acid from meth"lben%ene&A bromination, nitration, oxidationB bromination, oxidation, nitrationC nitration, oxidation, bromination

D nitration, bromination, oxidation

[PJC H2 2013 / Q24]

2. When ben%ene reacts with bromine in the resence of iron '((() bromide, what is the t"e ofreaction&A *lectrohilic substitutionB *lectrohilic addition

C +ree radical substitutionD +ree radical addition

[IJC H2 2013 / Q19]

. Which comound cannotbe made directl" from meth"lben%ene&

A B

C-

Cl

C-2Cl

C D

C-

r

C/2-

[AJC H2 2012 / Q20]$. Which roert" does ben%ene ha!e as a consequence of the delocalised electrons resent in its

molecule&A 0ddition reactions of ben%ene tae lace more easil" than substitution.

B en%ene is a good conductor of electricit".C ubstitution in ben%ene taes lace at one articular carbon atom.

D The carbon3carbon bond lengths are between those of C3C bonds and C4C bonds.

[DHS H2 2011 / Q21]

5. Which roert" of ben%ene results from the stabilit" associated with the ring of delocali%ed

electron cloud&A (t does not conduct electricit".B (t is suscetible to attac b" electrohiles.C (t undergoes electrohilic substitution instead of electrohilic addition.D 0ll the carbon#carbon bonds ha!e exactl" the same bond length.

[MJC H2 2011 / Q1]

6. 7uring the halogenation of ben%ene, a chlorine electrohile substitutes at a carbon atom. Which

one of the following gi!es the arrangement of the bonds at this carbon atom during the reaction&


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Arenes

at the start of thereaction

in the intermediatecomlex

at the end of thereaction

A lanar lanar lanar B lanar tetrahedral tetrahedralC lanar tetrahedral lanar

D tetrahedral lanar lanar [TPJC H2 2011 / Q22]

8. Chlorine gas was heated with 1,#dinitroben%ene in the resence of iron '((() chloride.

N/2

N/2

The structure of the roduct of the reaction is

A N/2

N/2

Cl

B N/2

N/2

Cl

Cl

Cl

Cl

C N/2

N/2

Cl

Cl

Cl

D N/2

N/2Cl

[MI H2 2011 / Q22]

9. When comound !was heated with acidified ;n/$, comound "was obtained.


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Arenes

"

Which of the following could be the structure of "&

AOH

OH

C

OH

OH

O

OB

OH

O D OH

O

[HCI 2012 / Q1#]


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Arenes

1. +a, Comlete the reaction scheme below b" drawing the structures of the organic comoundsin the boxes ro!ided.

C//-

N/2

CC-

C-2

limited Cl2, u! light

ste I

ste II

ste IIIC

C-

-

C-

ste IV

ste Vr

2'aq),

roomtemerature

C

C-

Cl

C- C

C-2Cl

-

C-

or

C

C-

-

C-

N/2

C

C-2r

/-

C-

+-, uggest reagents and conditions for stes Iand II b" comleting the table below.

+c, /utline the mechanism of the reaction of ste ..

(llustrate the mechanism statedb" writing suitable equations, showing clearl" the structureof reaction intermediate, and using curl" arrows to show the mo!ement of electrons.

[PJC/2013/ Q]

2. The molecule of ben%ene is a regular hexagon in which the electrons are described as beingdelocali%ed.'i) " using ben%ene as an examle, exlain, with the aid of a diagram, what is meant b" the term

delocalized electrons in benzene.

'ii) =i!e one h"sical and one chemical roert" which arise due to this structure.[MI H1 / IIB / Q1a]

. uggest one simle chemical test which wouldenable "ou to distinguish the following airs of

C-2C-

C-

2C-


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Arenes

comounds. tate reagent's) and condition's) andtheir corresonding obser!ations.

[TPJC H1 / IIA / Q$a]

$. en%"l chloride can undergo different t"es of reaction deending on the reagent and conditions

used. /ne of these reactions is used to con!ert ben%"l chloride to $#nitroben%"lchloride.

$#nitroben%"lchloride

tate and describe the mechanism undergone during the con!ersion shown abo!e.[IJC 10/ II / Q4-]

5. Comound E, 2#meth"lben%oic acid, is used as an intermediate for the s"nthesis of d"es and

esticides.

C

/-

/

C-

Comound E

C

/-

/

C-

Comound 0

.r

Comound can be formed when comound Eundergoes bromination.

+*, tate the reagents and conditions for the reaction.

+**, 0nother roduct, which is the isomer of comound is also formed in the reaction. 7raw the

disla"ed formula of the roduct.

+***, Name the t"e of reaction and describe the mechanism for this reaction, including curl" arrows

showing the mo!ement of electrons, and all charges.

[TJC 12/ III / Q2c]

6. 0 h"drocarbon, , has the molecular formula, C9-1>. (t reacts with chlorine either in the resence ofu! light or in the resence of 0lCl.


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Arenes

+a, 7raw an isomer of which uon reaction with chlorine forms a monosubstituted roduct

caable of rotating lane of olarised light.

+-, /ne ossible isomer of is 1,#dimeth"lben%ene.

+*, uggest the reagents and conditions for a reaction that could be used to distinguish between

1,#dimeth"lben%ene and "our answer in +a,. ?ou should describe what "ou will see for eachcomound.

+**,uggest the structure of the mononitrated roduct which is most liel" to be formed when

1,#dimeth"lben%ene reacts with concentrated nitric acid.

[CJC 12/ CA/ Q2]

8. The ben%ene ring usuall" resists chemical oxidation but the rocess ma" be accomlishedmicrobiologicall". The bacterium Pseudomonas putida in the resence of air raidl" con!ertsben%ene into comound .

+a, @sing the A/B notation for the oxidation of organic comounds, write a balanced equation forthis oxidation.

+-, (s comound oticall" acti!e& *xlain wh".

+c, (n the structure of comound , the two 3/- grous are on the same side of the lane ofthe ring, i.e. the 3/- grous are in a cisarrangement.

Comound S is a transisomer of comound .

7raw the structure of comound S showing clearl" the transarrangement.

[HCI 12/ II/ Q4+a,]

9. ;eth"lben%ene is also used to s"nthesi%e trinitrotoluene, TNT, according to the s"ntheticscheme below.

R

C-

te 1

C-

N/2 te 2

C-

N/2

N/2

te

C-

N/2

N/2

/2N

TNT

'C8-5N/6)


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Arenes

+*, uggest reagents and conditions for St' 1.

+**, Name the t"e of reaction and describe the mechanism for St' 1, including curl" arrows showingthe mo!ement of electrons, and all charges.

+***, *xlain wh" comound Aoccurs in !er" small amounts in the roducts of St' 2.

+*5, *xlain wh" more rigorous conditions are necessar" for St' 3comared to St' 2.

[HCI 12/ III/ Q2+-,]

C-

N/2

/2N

A


10/88


11/88

&$ Halo en

Halogen Derivatives

1 1 mole of an organic comound P undergoes elimination on reaction with ethanolic sodiumh"droxide to form 2 moles of -r. What could P be&

A B

C D

[AJC / MCQ / Q23]

2 1#bromoroane can be con!erted to 2#bromoroane in the reaction scheme below.

Which set of reagents for ste I and ste II would be most suitable&te I te II

A -ot aqueous /- rB -ot /- in ethanol -rC -ot concentrated -2/$ 0queous bromineD -"drogen gas with nicel catal"st romine in the resence of ultra!iolet light

[AJC H1 / MCQ / Q21]

*xeriments are carried out on three comounds,P, Qand . 0 samle of >.>1 mol of each comoundis refluxed with $> cm of 1 mol dm#of Na/-'in excess). *xcess aqueous sil!er nitrate is addedto the resulting mixture after acidification in each case

and the mass of the reciitate weighed. What is themass in grams, of the reciitate formed b" eachcomound&

P Q A $.1 $.1 $.1

B 2.98 2.98 1.$$C 2.98 $.1 1.$$D 1.$$ $.1 1.$$

[ACJC / MCQ / Q22]

$ 0 susension of 1,,$#trichloroc"clohexane is stirred in aqueous sodium h"droxide. -ow man"of the chlorine atoms in each molecule will be remo!ed b" h"drol"sis&A > B 1 C 2 D

[ACJC H1 / MCQ / Q21]

C

Cl

-

Cl

C

-

-

C

/

Cl

C

C

Cl

-

C

- Cl

-

-

Cl

C

-

-

-

ClCl

C-

-

C

Cl

-

C

-

-

-

P Q


12/88

Halogen Derivatives

5 Which of the following statements best exlains wh" fluoroalanes are the least reacti!ehalogenoalanes&A +luorine is much more electronegati!e than carbon.B The +Dion is the most stable halide ion.C The C3+ bond is the most olar carbon3halogen bond.D The C3+ bond is the strongest carbon3halogen bond.

[HCI / MCQ / Q2][HCI H1 / MCQ / Q24]

6 2,$,6#trinitrohen"l deri!ati!es are bright "ellow cr"stalline comounds that can be formed b"the following reaction.

The t"e of reaction mechanism shown abo!e isA *lectrohilic substitution B *lectrohilic additionC Nucleohilic substitution D Nucleohilic addition

[IJC / MCQ / Q10]

8 Which one of the following, in alcoholic solution, roduces a reciitate most raidl" whenwarmed with aqueous sil!er nitrate&A 1#chlorobutane B 1#bromobutaneC 1#iodobutane D chloroben%ene

[MI / MCQ / Q23]

9 -"drogen bonding is not resent inA C-Cl B C-N-C- C C6-5/- D C6-5C//-

[MI / MCQ / Q2$]

< 0 halogen comound was boiled under reflux for some time with aqueous sodium h"droxide.The resulting mixture was cooled, treated with dilute nitric acid, followed b" the addition ofaqueous sil!er nitrate. No yellow precipitate was seen. Which one of the following could be&

[MI H1 / MCQ / Q1#]

1> The following shows the andme"er reaction toroduce iodoben%ene from hen"lamine. Whatt"e of reaction is in!ol!ed in ste 2&A +ree radical substitution B *lectrohilic substitutionC Nucleohilic substitution D *limination

[NJC / MCQ / Q22]


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Halogen Derivatives

11 Which one of the following comounds gi!es the greatest number of alenes when it is reactedwith hot alcoholic otassium h"droxide&A B

C D

[NJC H1 / MCQ / Q20]

12 (n the Wurt% reaction, two halogenoalanes react with sodium metal to form a new carbon#carbon bond, resulting in the formation of a new alane:

EDF G EHDF G 2Na EDEH G 2NaF

Which of the following does not show the correct roduct when the stated reactants arereacted together in a Wurt% reaction&

A C-r G C2-5( G 2Na C-C-2C- G Nar G Na(

B .r

G C-

.r

G 2Na

C-G 2Na.r

C Cl

r

G 2Na G NaCl G Nar

Dr

G G 2Na G 2NarC-2r

[SJC 2011 / MCQ / Q24]

1 What is the roduct of a nucleohilic substitution reaction between 2#iodobutane and sodiumethoxide 'C-C-2/

NaG)&

A C-C-4C-C- B C-C-2 C-'/C-)C-2C-C C-C-2 C-'C-)/C-2C- D 'C- )2C-C-2 /C-2C-

[N6JC / MCQ / Q22]

1$ ome chlorobutanes were searatel" treated with hot ethanolic sodium h"droxide. Two ofthese ga!e the same h"drocarbon, C$-6.+rom which air of chlorobutanes was this h"drocarbon obtained&

A C-C-2C-2C-2Cland C-C-2C-2C-Cl2

B C-C-ClC-C

lC-and C

lC-2C-2C-2C-2C

l

C C-C-ClC-2C-and ClC-2C-2C-2C-2Cl

D C-CCl2C-2C-and ClC-2C-2C-2C-[N6JC / MCQ / Q23]


14/88

Halogen Derivatives

15 Which of the following halides will react most raidl" with aqueous sodium h"droxide&A 'C-)CI B 'C-)Cr C 'C-)CCl D 'C-)C+

[N6JC H1 / MCQ / Q1$]

16 /rganic comound "undergone the following successi!e reactions:( reaction with h"drogen chloride

(( boiling with aqueous sodium h"droxide((( reaction with hot concentrated hoshoric acid

The final organic roduct was ethene. Which of the following could most liel" be comound "&A *thene B *thanol C Chloroethane D *thanoic acid

[SJC / MCQ / Q24][SJC H1 / MCQ / Q19]

18 (n the uer atmoshere, chlorofluoroalanes 'C+Cs) are broen down to gi!e chlorine but notfluorine radicals. What is the best exlanation for this&

A +luorine is more electronegati!e than chlorine.B The C#+ bond is longer than C#Clbond.C The C#+ bond is stronger than C#Clbond.D The chlorine atom is larger than the fluorine atom.

[SJC H1 / MCQ / Q1]

19 (n which of the following reactions is the inorganic reagent acting as a nucleohile&A

B

C

D

[TJC / MCQ / Q2#]

1< When 'chlorometh"l)ben%ene, C6-5C-2Cl, is treated in succession with two reagents O andP, it gi!es hen"lethanoic acid, C6-5C-2C/2-. Which of the following is a ossiblecombination for reagents Oand P&

O PA Na/- 'aq) 2Cr2/8'aq)B Cl2'aq) Na/- 'aq)C -CN '(n resence of alaline) dilute -ClD NaCN 'in aqueous ethanol) dilute -2/$

[TJC / MCQ / Q29]

Cl2 + -Cl+

Cl2+C-24C-2 ClC-2C-2Cl

:I

C-2I

+ :Cl+

C-2Cl

r2

C-2r

G -rG

C-


15/88

Halogen Derivatives

2> (n which comound is the carbon#halogen bond most easil" h"drol"sed b" Na/- 'aq)&A chloroben%ene B bromoroane C fluoroethane D 2,$,6 3 trichloroben%ene

[TPJC H1 / MCQ / Q1$]

21 Which sequence shows the'rong order of increasing ease of hydrolysis?

% CH3CH2Br < CH3CH2* < C6H5CH2Cl ( C6H5CH2Cl < C6H5CH2Br < CH3CH2*C CH3CH2F < C6H5CH2Br < CH3CH2* ) CH3CH2Cl < CH3CH2Br < CH3CH2*

[.JC H1 / MCQ / Q23]

22 0 reaction sequence is gi!en below. Which one of the following structures reresents theroduct Q&

C-rC-

r

A B

C D

[6JC / MCQ / Q24]

2 7ichlorodifluoromethane, CCl2+2, is a widel" used aerosol roellants and as a refrigerant.Which statement hels to exlain wh" dichlorodifluoromethane is chemicall" inert&A The carbon#fluorine bond energ" is large.B The carbon#fluorine bond has low olarit".C +luorine is highl" electronegati!eD Ian der WaalsJ forces between the molecules are wea

[6JC H1 / MCQ / Q19]

2$ 0 bromoalane, ", was heated under reflux with alcoholic otassium c"anide solution. The

organic roduct formed was then heated under reflux with dilute sulhuric acid. +rom thismixture, 2#meth"lroanoic acid was obtained. Which of the following comounds could be"&A 1#bromoroane B 2#bromoroaneC 1#bromobutane D 2#bromobutane

[6JC H1 / MCQ / Q22]

CN

ethanolP

dil -Cl

refluxQ

C-C-,

.r

C/2-

C-C-,

-//C

C/2-

C-C-

Cl

C-2N-

2

C-C-

Cl

C//-


16/88

Halogen Derivatives

+or each of the following questions, one or more of the three numbered statements 1 to 3ma"be correct. 7ecide whether each of the statements is or is not correct. The resonses A to Dshould be selected on the basis of:

A B C D

1, 2and 3

are correct

1and 2onl"

are correct

2and 3onl"

are correct

1onl" is

correct

1 The formulae of two halogenoalanes are gi!en below. C2-5Cl C2-5rWhich statements about the two comounds are correct& " 61 The induced diole#induced diole forces in F are stronger than those in ?.2 The C#Clbond is more olar than C#r bond.3 The C#Cl bond in F is harder to brea than the C#r bond in ?.

[TPJC / MCQ / Q3][TPJC H1 / MCQ / Q30]

St%&ct&%'( Q&')t*on)

1 7"lan was ased b" his chemistr" tutor to differentiatethe three comounds below.7"lan suggested the following method:Step 1: To each of the 3 unno!ns" add 1 cm3of a#ueous $a%H.Step &: Then add 1 cm3of a#ueous silver nitrate.Step 3: 'ollo!ed b( a#ueous h(drochloric acid" until blue litmus turns red.(dentif" and exlain the three errors in 7"lanHs method.

[HCI / II / Q4 a +7o(*8*'(,]

2 Comound A, 1#chlorobutane reacts with ethanolic sodium c"anide to "ield roduct, B.'a) With the aid of equations, name and describe the mechanism of the reaction and gi!e the

structural formula of B.'b) *xlain how the rate of this reaction changes when 1#chlorobutane is relaced b" 1#

bromobutane.[MI / II / Q# a - ]

The h"drol"sis of the halogenoalanes shows a trend which can be related to their bonding.The table below shows the obser!ations after aqueous sil!er nitrate is added to eachhalogenoalane samle.

Comound /bser!ationsC-C-IC-2C- reciitate forms almost immediatel"

C-C-rC-2C- reciitate forms after 2 minutes

C-C-ClC-2C- reciitate forms after 1> minutes

'i) " quoting suitable !alues from the Data )oolet, exlain the abo!e obser!ations for theh"drol"sis of halogenoalanes.

'ii) redict, with a reason, whether a reciitate will be formed when aqueous sil!er nitrate isadded to C-C-+C-2C-.

[N6JC H1 / IIB / Q# ( ]$'a) When roane, C-C-2C-, reacts with chlorine, two different monochlororoanes are

roduced.'i) What condition is used for this reaction&'ii) 7raw the disla"ed formula of the two roducts'iii) tate the t"e of isomerism shown in the two roducts.


17/88

Halogen Derivatives

'i!)When the two roducts are refluxed with ethanolic otassium h"droxide, a comound Bwasformed, which could raidl" decolourise bromine in CC l$. =i!e the disla"ed formula of B, andwrite a balanced equation for the reaction between Band bromine in CCl$.

'b) Chlorofluorocarbons, C+Cs, are small alane molecules where a few of the h"drogen atomsha!e been relaced b" chlorine atoms and fluorine atoms. What are C+Cs used for, whaten!ironment ha%ard do the" ose, and how, chemicall", does this ha%ard arise.

[6JC H1 / IIB / Q# ( ' ]

5 *th"lben%ene can react with chlorine in two wa"s, deending on the conditions of the reaction.'i) tate the condition needed for reaction I.'ii) 7escribe a test to distinguish between

Aand B. tate the reagents, conditions,and the obser!ations for each comound.Write balanced equations for an" reactionsthat occur.

[6JC H1 / IIB / Q$ c ]

6 The grah below shows the reaction between aqueous sodium h"droxide and

a solution of a saturated al"l chloride at temerature ToC.

'a) Eeferring to the grah abo!e, deduce the order of reaction with resect to sodiumh"droxide and E*land hence write down the rate law.

'b) (s E*l most liel" to be a rimar", secondar" or tertiar" al"l halide&

'c) 7raw a labelled energ" rofile diagram for the reaction.

'd) riefl" exlain how one of the grahs abo!e ma" be obtained exerimentall".

'e) 0queous h"drochloric acid and 'C-)2CC-*lare searatel" reacted with aqueoussodium h"droxide. -ow would the rates of reaction of these two comounds comarewith the rate of reaction of E*lin 'b) abo!e& =i!e "our reasons.

C-2C-

C(

C-2C-

2ClC-

2C-

Cl2 Cl2

AB

reaction ( reaction ((

Timea

[E*l] = x mol dm#

AE*lB 4 2x mol dm#

ANa/-BK mol dm#

>.1

>.>5


18/88

Halogen Derivatives

E))a Q&')t*on)

1 uggest methods b" which the following airs of comounds could be distinguished from each

other b" chemical tests. The distinguishing of some of these airs ma" rel" on a reliminar"breaing#u of the comounds and subsequent testing of the reaction roducts.

[AJC / III / Q c *** ]

2 hen"lethene, commonl" nown as st"rene, is roduced in industrial quantities from ben%eneand eth"lene !ia the intermediate eth"lben%ene. (t is used as a monomer to mae lastics suchas ol"st"rene. Low le!els of st"rene occur naturall" in lants as well as a !ariet" of foods such

as fruits, !egetables, nuts, be!erages, and meats. 1#bromo#1#hen"lethane and 2#bromoeth"lben%ene can be obtained from hen"lethene and eth"lben%ene resecti!el".7escribe a chemical test to distinguish 1#bromo#1#hen"lethane from 2#bromoeth"lben%ene.

1-bromo-1-phenylethane 2-bromoethylbenzene

[HCI / III / Q2 c * ]

When a mixture of ber"llium h"droxide ellets and ethanol is added to 2#chlorobutane, P, Q, and S are formed. 0lthough P, Q and do not react with Cl5, the" decolourise otassiummanganate 'I((), with onl" gi!ing an effer!escence. S has the formula of C#H14O and isfound to rotate lane#olarised light.

'i) uggest the identities of P, Q, and S, exlaining "our reasoning.'ii) /utline a mechanism for the formation of S from the reaction described abo!e.

[NJC / III / Q ( ]

$ The following concerns the reactions of some organic halogen deri!ati!es.

'i) 7escribe the mechanism of the reaction between iodomethane and aqueous sodiumh"droxide.

'ii) *xlain wh" the abo!e reaction taes lace !er" easil" whereas conditions of 6>MC and 15>atmosheres are required to con!ert chloroben%ene to henol.

[N6JC / III / Q1 c * *** ]

5 0 halogenoalane, , with a labelled carbon, C, undergoes the following reaction:

'i) tate the reagents and conditions for the abo!e reaction.

'ii) tate the t"e of h"bridisation and the shae with resect to the carbon atom, C , before and

after the reaction.


19/88

Halogen Derivatives

'iii) 7escribe a chemical test that would distinguish comound from chloroben%ene.[TJC / III / Q1 ' ]

6 The table below lists some information about fi!e comounds, two of which arechlorofluorocarbons 'C+Cs).

Na7' St%&ct&%' :a77a-*:*t ;*8't*7' / 'a%)

C+C#11 CCl+ No 85

C+C#12 CCl2+2 No 1>9

-C+C#22 C-Cl+2 No 22

-C+C#12 C-Cl2C+ No 2

-+C#152 C-C-+2 ?es 2

'i) 0rrange the abo!e h"drochlorofluorocarbons '-C+Cs) and h"drofluorocarbons '-+Cs)comounds in order of increasing boiling oints. *xlain "our answer in terms of structure andbonding.

'ii) =i!e one use of C+Cs in e!er" da" life.'iii) *xlain wh" the use of C+C oses a roblem to the en!ironment.'i!) -"drochlorofluorocarbons '-C+Cs) and h"drofluorocarbons '-+Cs) are ossible relacements

for C+Cs. Which comound in the abo!e table is the best choice& *xlain "our answer.[TJC / III / Q3 a ]

8 *xlain wh" chloroethane undergoes nucleohilic substitution but not chloroben%ene.[6JC / III / Q1 ( ]


20/88

H(dro+( *ompounds

1 When an organic comound Q was treated with hoshorus entachloride, fumes of h"drogen

chloride were e!ol!ed. When Q was warmed with alaline aqueous iodine, a "ellow reciitate

was formed. Which of the following was Q> cm, 15> cmand 2>>

cm. Which sequence of comounds matches these results&

1>> cm 15> cm 2>> cm

A R E

B E RC R E D E R

[SJC / MCQ / Q2]

2 The inacol rearrangement in!ol!es the reaction of a diol in acidic conditions to form a

carbon"l comound as shown below.


25/88

H(dro+( *ompounds

C C

C-

/-

C-

C-

/-

C-

- G

G -2/

2, #dimeth"lbutane#2,#diol , #dimeth"lbutan#2#one

C C

/

C-

C-

C-

C-

Which of the following structural formulae is not a roduct of the inacol

rearrangement of 2,#dihen"lentane#2,#diol with the structure as shown below&

C C

C-2C-

/- /-

C-

2,#dihen"lentane#2,#diol

A

C C/

C-2C-

C-

B

C C

/

C- C-2C-

C

C C

/

C-2C- C-

D

C C/

C- C-

C-2

[PJC H2 2011 / Q2]

2$ (n arearation of roene, roan#1#ol is added a dro at a time to a heated reagent P. The

imure roene is washed b" being bubbled through a solution Qand then collected.

Which one of the following is a ossible combination for reagents Pand Q&


26/88

H(dro+( *ompounds

P Q

A acidified 2Cr2/8 dilute Na/-

B %inc metal dilute -Cl

C concentrated -2/$, dilute Na/-

D ethanolic Na/- concentrated -2/$ [TJC H1 / MCQ / Q21]

25 Comound E, C9-


27/88

H(dro+( *ompounds

A B

C D

[.JC / MCQ / Q22]

2< The comound reacts with

% hot HCl(aq) to form ( NaOH(aq) to form

C HCl in CCl4to form ) hot acidic KMnO4to form

[.JC / MCQ / Q24]

> What are the products formed when compound, is treated with an excess of hot acidicKMnO4?

CH2=C(CH3)CH=CHCH2CH2OH

Comoun* ,

A

B

C

D

[.JC H1 / MCQ / Q20]

1 Which one of the following will be formed when pentan-1,4-diol is distilled with hot acidified

potassium dichromate(V*)?


28/88

H(dro+( *ompounds

% CH3COCH2CH2CHO ( CH3COCH2CH2COOH

C CO2and HOOCCH2CH2COOH ) CH3CH(OH)CH2CH2CHO

[.JC H1 / MCQ / Q21]

2 Which of the following comounds:'i) is unaffected b" hot alaline otassium manganate'I(() and

'ii) gi!es h"drogen when treated with sodium&

A 'C-)2C-C/C- B 'C-)C/- C 'C-)2C-C-2/- D C-C-2C-'/-)C-[6JC / MCQ / Q30]

+or each of the following questions, one or more of the three numbered statements 1 to 3ma" becorrect. 7ecide whether each of the statements is or is not correct. The resonsesA to Dshouldbe selected on the basis of:

A B C D

1, 2and 3are correct

1and 2onl"are correct

2and 3onl"are correct

1onl" iscorrect

1 Which of the following reagents can be used to distinguish between the following twocomounds&

1 r2'aq) 2 ;n/$ 3 Na[AJC / MCQ / Q3]

2 The relati!e molecular mass of the organic comound increases when ethanol reacts with

1 acidified otassium chromate'I() solution followed b" distillation.

2 acidified otassium manganate'I(() solution.

3 sodium bromide and concentrated sulhuric acid.


Chloroethane can be reared from bromoethane as follows:

C2-5r C2-5/- C2-5Cl

What deductions can be made about the abo!e reaction sequence&

1 te >in!ol!es nucleohilic substitution.

1 -ot aqueous sodium h"droxide is the reagent in ste >.

3 te Hcan tae lace at room temerature.

[MI / MCQ / Q39]

$ Which of the following is TUE&

1 ;ore branching of molecules results in an increase in boiling oint.2 0s the number of carbon atoms increases, solubilit" of alcohols in water decreases.

3 ;eth"lben%ene has a higher melting oint than ben%ene.

[MI H1 / MCQ / Q2#]

ste > ste H


29/88

H(dro+( *ompounds

5 ;onomer A reacts with dihenol B to gi!e a ol"mer as shown in the reaction scheme below.

Which statement's) isKare correct&

1 (n the reaction, nucleohilic substitution taes lace.2 /ne mole of -Clis remo!ed for each unit of the ol"mer formed.

3 oth monomer B and the ol"mer formed gi!e a urle comlex with neutral iron '((()

chloride solution.

[MJC / MCQ / Q40]

6 Which of the following airs of comounds gi!e the same organic roducts when subSected to

a hot solution of acidified otassium manganate 'I(()&

1

2

3 C-C-2C-2/- and C-C-'/-)C-


8 Which of the following comounds forms a "ellow reciitate when warmed with alaline

aqueous iodine&

1 utan#2#ol 2 1#hen"lethan#1#ol 3 2#hen"lethanol


30/88

H(dro+( *ompounds

[N6JC / MCQ / Q3]

9 inaacr"l is used as a fungicide.+rom an examination of its structure,

it can be deduced that

1 its aqueous solution will be acidic.2 it cannot exist in oticall" acti!e forms.

3 it will react with ethanol in the resence of concentrated sulhuric acid to

gi!e an ester.

[TJC / MCQ / Q39]


1 0lcohols often ha!e an odor described as HbitingH that HhangsH in the nasal assages. 0lchohol in

the form of be!erages has been consumed b" humans since re#historic times, for a !ariet" of

h"gienic, dietar", medicinal, religious, and recreational reasons. While infrequent consumtion

of alchohol 'eseciall" ethanol) in small quantities ma" be harmless or e!en beneficial, largerdoses result in drunenness or intoxication 'which ma" lead to a hango!er as the effect wears

off) and, deending on the dose and regularit" of use, can cause acute resirator" failure or

death and with chronic use has medical reercussions. ecause alcohol imairs Sudgment, it

can often be a catal"st for recless or irresonsible beha!ior. elow show the formulae of two

different alcohols, A and B.

C-C-'/-)C-2C- 'C-)C/-

A B

7escribe one chemical test b" which A could be distinguished from B. ?ou should state the

reagents and conditions "ou would use and the obser!ations "ou would mae with each

comound undergoing the test.

[IJC H1 / IIA / Q1 ]

2 ices are often resonsible for the fla!our in man" foods. Two t"es of comounds resent in

one of the sices are shown below :

What would be obser!ed when the following reactions are carried out&

(n each case, gi!e the name or formula of the reaction roduct which is resonsible for the

obser!ation "ou ha!e made.

'i) ubstance E with Cl5.

'ii) ubstance E with sodium metal.

'iii) ubstance with hot acidified otassium manganate 'I(().

'i!) uggest how E could be con!erted into in the laborator".

[IJC H1 / IIB / Q1 c ]

There are two different alcohols that ha!e the molecular formula C-9/.


31/88

H(dro+( *ompounds

7raw the disla"ed formula of the 2 isomers and suggest a chemical test that can be used to

distinguish them. (nclude an" obser!ations that would be seen.

[SJC H1 / IIB / Q1 8 ]

$ ;enthol, C1>-2>/, can be s"ntheticall" made from eermint

and is used in sin lotions to reduce itching. The structural formulaof menthol is shown:

'a) Label all the chiral carbons 'with ) in the structure shown

abo!e.

'b) ;enthol can be used in the following reaction scheme:

'i) uggest reagents and conditions for tes 1and 2.'ii) uggest the structural formula of the intermediate comound ".

'c) Comound 6, a structural isomer of menthol, gi!es a "ellow reciitate on warming with

alaline aqueous iodine. uggest a structural formula of the isomer6.

[TPJC / II / Q$ ]

[TPJC H1 / IIA / Q ]

5 uggest how the three alcohols 'namel" butan#1#olP butan#2#ol and 2#meth"lroan#2#ol) could

be distinguished from each other exerimentall". (nclude obser!ations where aroriate.

[TPJC H1 / IIB / Q10 c ]

6 @se the information below to identif" the comounds A to E. *xlain "our reasoning.

Compounds% and( each has a relative molecular mass of 60 and an empirical formula of

C3H8O. During the reaction with acidified potassium dichromate (VI) solution,% forms only one

organic product,C. Under similar conditions,Bproduces compound) which can be further

oxidised toE.

[.JC H1 / IIB / Q$ a * ]

E))a Q&')t*on)


32/88

H(dro+( *ompounds

1 uggest methods b" which the following airs of comounds could be distinguished from each

other b" chemical tests. The distinguishing of some of these airs ma" rel" on a reliminar"

breaing#u of the comounds and subsequent testing of the reaction roducts.

'i)

'ii)

[AJC / III / Q c * ** ]

2 7escribe a simle chemical test that "ou could use to distinguish the following comounds. ?ouare to include reagents and conditions, obser!ations and a balanced equation's) in each case.

'i) 'ii)

[ACJC / III / Q1 ( ]

Concentrated sulfuric acid reacts with man" organic comounds, forming water as one of the

roducts. Three examles are shown below.

Concentrated sulfuric acid deh"drates methanoic acid to form a gas, A, with the same

molar mass as ethene.

Concentrated sulfuric acid deh"drates sucrose, C12-22/11, to form a blac solid, B.

Concentrated sulfuric acid deh"drates ethane#1,2#diol to form a comound C with a molar

mass of 99 g molD1. (n this reaction, 2 moles of ethane#1,2#diol roduce 1 mole of C and 2

moles of -2/.

uggest the identities of A B an( C. Write equations for each reaction and deduce the

structural formula of C. [HCI / III / Q18 ]

$ +or each of the following airs of comounds, suggest methods of not more than two stes, b"

which the" can be distinguished from each other. tate the reagents and conditions clearl" and

describe what "ou would see.

/-

C

/ C-,

C

C-2/-

/ -

and/

/

/

/

and


33/88

H(dro+( *ompounds

'i)

and

'ii)

and [IJC / III / Q3 ' ]

5'i)Comound D can undergo the following reaction.

=i!en that the roduct E is not chiral, suggest a ossible structure of E. 0nd hence, deduce the

structure of CH12O4.

'ii) is another ossible roduct from ste I. -owe!er, contains a chiral centre and it forms a

ol"mer in ste II.

uggest a ossible structure of and exlain wh" does not form the same t"e of roduct as

E in ste II when it is treated with concentrated sulhuric acid.

[NJC / III / Q2 a ** *** ]

6 uggest one simle chemical test which would enable "ou to distinguish the following airs of

comounds. tate reagent's) and condition's) and their corresonding obser!ations.

comound C comound 7 [TPJC / III / Q3 a ** ]

8 The benzaldehyde can be reduced to phenylmethanol, C6H5CH2OH, which has a different

acidity from that of phenol, C6H5OH. Explain the difference in acidity between phenylmethanol

and phenol.

[.JC / II / Q4 c ]

' Uoseh riestl" reared h"drogen chloride in 1882 and found that the comound was acolourless gas at room temerature. (t formed white fumes of h"drochloric acid uon contact

with atmosheric humidit". -"drogen chloride gas as well as h"drochloric acid are imortant in

technolog" and industr".

-,C#-C4C-#C-

2#C#C-

,

/-

-

'C-,)2C4C-#C#C-

,

/-

C-,


34/88

H(dro+( *ompounds

*xamles of alications include h"drochlorination of rubber, treatment of cotton

wool, semiconductor industr", etc. 7raw the structural formulae of the organic

roducts formed when the comound 'shown on the right) reacts with:

0: -Cl'g), VnCl2 : C-C//-, hot concentrated -2/$

[6JC / III / Q2 ( * ]

< When henol is added to aqueous sodium h"drogencarbonate, there is no e!olution of gas, but

a colourless gas is e!ol!ed when 2,$,6#trinitrohenol is used instead. *xlain the abo!e

obser!ation as full" as ossible, writing a balanced equation for the reaction that occurred.

[6JC / III / Q4 c ** ]


35/88

*arbon(l *ompounds

1 /xidation of an alene 6 gi!es a diolP further oxidation gi!es a dietone. Which one of the

following could be6&

A C-C-4C-2 B C-C-4C-C- C C-C-4C'C-)2 D 'C-)2C4C'C-)2 [AJC / MCQ / Q21]

2 %estrone, a sex hormone, has the following structural formula.

Which reagent would be exected to react with this comound&

A lithium aluminium h"dride B concentrated sulhuric acidC alaline aqueous iodine D acidified otassium manganate'I(()

[AJC / MCQ / Q2$]

Which one of the following reresents the final roduct obtained when the

alene below is reacted with cold, alaline manganate'Ill) ions followed b" hot

acidified otassium dichromate'Il) solution&

A B

C D

[N6JC H1 / MCQ / Q2]

$ *itronellol is a colourless oil" liquid ha!ing a rose#lie odour. (t is the acti!e ingredient in o!er

> essential oils and is a maSor comonent in erfumes, cosmetics and soas. (t ma" be

reared s"ntheticall" from comound ! using reagent ".


36/88

*arbon(l *ompounds

Which of the following could ! and " most liel" be&

A

B

C

D

[HCI H1 / MCQ / Q21]

5 *thanal can react with ammonia as shown.

C-C-/ G N-Q C-C-'/-)N-2

What t"e of reaction is this&A addition3eliminationB electrohilic additionC free3radical additionD nucleohilic addition [AJC H2 2011 / Q2]

6 ;eth"l isoc"anate, C-#N4C4/, readil" reacts with nucleohiles. " analog" with thechemistr" of other carbon"l comounds, redict which atom will be attaced b" a nucleohile.

A carbon atom of the isoc"anate grou B carbon atom of the meth"l grouC nitrogen atom D ox"gen atom

[SJC / MCQ / Q2$]


37/88

*arbon(l *ompounds

8 The mechanism below shows how butanone reacts with h"drogen c"anide.

Which of the following statements is true&

A The roduct mixture is oticall" acti!e.B The rate of reaction of h"drogen c"anide with butanal is faster than that with butanone.

C C"anoh"drin roduced can react with ammonia at high ressure to form amine.

D C"anoh"drin roduced requires otassium manganate'I(() to form carbox"lic acid.

[ACJC H2 2011 / Q24]

9 *thanal reacts with CNDfrom -CN in the resence

of a wea base as shown.

(n a similar reaction, DC-2C/C-ions are generated

when C-C/C-reacts with a strong base. Which

one of following comounds is the roduct when ethanal reacts with DC-2C/C-&

A C-C-'/-)C-2C/C- B 'C-)2C'/-)C-2C-/

C 'C-)2C'C-/)C-2/- D 'C-)2C'/-)C/C-

[NJC / MCQ / Q2]


38/88

C C-C

-

-

C

CN

/-

C-

-

-

C C-C

-

-

C

C//-

/-

C-

-

-

C C-C

-

-

C

-

C

-

-

-

/-

CN

-

C C-C

-

-

C

-

C

-

-

-

/-

C//-

-

C-C

-

-

C C-

CN

/-

C-C

-

-C C-C//-

/-

C C-C

-

- -

-

C C-

/-

CN

C C-C

-

- -

-

C C-

/-

C//-

*arbon(l *ompounds

< entan#2#one is treated with cold h"drogen c"anide in the resence of traces of sodium

c"anide. The roduct "of this reaction is then boiled with h"drochloric acid to gi!e 6. What

are " and6liel" to be&

A

B

C

D

[SJC / MCQ / Q2]

1> Which of the following reagents will gi!e similar results for both butanal and butanone&

A 0queous alaline iodine B +ehlingJs solution

C 0cidified aqueous otassium dichromate'I() D 2,$#dinitrohen"lh"dra%ine[AJC H1 / MCQ / Q2]

11 Comound B will show a ositi!e test with all of the

following reagents '?c't

A r, reflux

B 2,$#dinitrohen"lh"dra%ine, warm

C 0cidified ;n/$, reflux

D Na, room temerature

[IJC H1 / MCQ / Q24]

12 The first stage in the s"nthesis of anti"rine, a drug used in reducing fe!er, is the


39/88

*arbon(l *ompounds

reaction between comound Tand hen"lh"dra%ine.

N-N-2C-C/C-2C/2C-2C- G

T

S

What will be the roduct S&

A N-C/C-2C/C-

B N-C-2C/2C-2C-

C N-N-2C-C/C-2C/

D N- N C

C-

C-2C/2C-2C-

[DHS H2 2011 / Q24]

1 Comound A has the following formula.

Which one of the following statements is *nco%%'ct about Comound A&

A 0 white reciitate is formed when aqueous sil!er nitrate is added.

B 0n orange reciitate is formed with 2,$#dinitrohen"lh"dra%ine.

C 0 ale "ellow reciitate is formed when warmed with alaline

aqueous iodine.

D 0n acidified solution of ;n/$decolourised on heating. [NJC H1 / MCQ / Q24]

1$ Which of the following reagents will cause a colour change when the reagent is added to

comound P&

A warm, alaline aqueous iodine B 2,$#dinitrohen"lh"dra%ineC hot, acidified ;n/$ D +ehlingJs reagent

N6JC H1 / MCQ / Q21]

15 Limonene, A, occurs in oil of lemons and is used to fla!our some citrus drins.

Which of the following is true about limonene?

A (t exhibits geometric isomerism.

( Upon reaction with hot acidified potassium manganate (I((), the product

forms an orange precipitate with 2,4-dinitrophenylhydrazine.

C It reacts with bromine dissolved in an inert solvent to form a compound

with the molecular formulaC1>-16r2.

D (t reacts comletel" with 1 mole of h"drogen in the resence of a nicel

catal"st to "ield a saturated comound.

[MJC H1 / MCQ / Q19]

16 Which reagent gi!es the same !isible result with roanal and with roan#2#ol&


40/88

*arbon(l *ompounds

A +ehlingJs reagent B concentrated sulhuric acid

C acidified otassium manganate 'I(() D 2,$#dinitrohen"lh"dra%ine

[TJC H1 / MCQ / Q24]

18 /estrone is a female sex hormone.

-ow does the comound abo!e reacts with 2,$#

dinitrohen"lh"dra%ine reagent '2,$#7N-), TollensJ reagent and+ehlingJs reagent&

2,$#7N- TollensH +ehlingHs

A negati!e negati!e negati!e

B ositi!e negati!e negati!e

C ositi!e ositi!e negati!e

D ositi!e ositi!e ositi!e [ACJC H1 / MCQ / Q24]

19 Comound Q was subSected to the following tests and the results are recorded below. Which of

the following could be comound Q&

Eeagent and conditions obser!ations

0cidified ;n/$, warm olution turns from urle to colourless. C/2 is

e!ol!ed.

+ehlingJs reagent, warm No reciitate seen.

TollenJs reagent, warm il!er mirror obser!ed.

A B C D

[HCI / MCQ / Q22]

1< The comound C-8r undergoes a sequence of reactions as follows:

C-8r - / 0 sil!er mirrorWhat could be the formulae for F, ? and V&

" 6

AC-C-2C-2/- C-C-2C/2- C-C-2C-/

BC-C-2C-2/- C-C-'/-)C-2/- C-C/2-

CC-C-2C-2/- C-C-2C-/ C-C-2C/2-

D C-C-'/-)C- C-C/C- C-C/2-

[MI H1 / MCQ / Q1]

[N6JC H1 / MCQ / Q20]

OH(aq) Acidified

K2Cr2O7

Tollens

rea!en"


41/88

*arbon(l *ompounds

2> -ow man" structural isomers with the molecular formula C$-9/ can reduce TollenJs reagent

to form a sil!er mirror&

A 1 B 2 C D $[6JC H1 / MCQ / Q24]

21 0n organic comound > is refluxed with acidified otassium manganate 'I(() to roduce 2organic comounds H, I and an odourless gas. H ga!e negati!e results with +ehlingJs reagent

but ga!e a ale "ellow reciitate with iodine in an alaline solution. *ffer!escence was

obser!ed when Iwas treated with aqueous sodium carbonate.oth H and I were found to "ield

orange cr"stals when treated with 2,$#dinitrohen"lh"dra%ine.

What is the structure of,?

A B

C D


22 The table shows the obser!ations of the chemical tests conducted on comound U.

Chemical test /bser!ations

Warm with 2,$#dinitrohen"lh"dra%ine /range reciitate

Warm with TollensJ reagent il!er mirror

Warm with alaline aqueous iodine ?ellow reciitate

+rom the obser!ations of the chemical tests, what could Ube&

A C-C-/ B C-C/C- C C-C-2C-/ D C-C-'/-)C-[N6JC H1 / MCQ / Q22]

2 0n organic comound has the following roerties.(t gi!es a "ellow reciitate with aqueous alaline iodine. When warmed with acidified

otassium dichromate'I(), the solution remains orange.

Which one of the following is the organic comound&

A B

C D

[NJC / MCQ / Q21]

[NJC H1 / MCQ / Q2]


42/88

*arbon(l *ompounds

2$ When an alcohol, H, is treated with hot acidified aqueous otassium manganate'#II), the final

oxidation roduct gi!es a ositi!e tri#iodomethane test. Which of the following comounds

could corresond to H&

A C6-5C-2/- B C2-5/- C C-C-'/-)C2-5 D C6-5C-'/-)C2-5

[TJC / MCQ / Q21]

25 How many structural isomers with the molecular formula C4H8O2(exclude ether) give an

orange precipitate with 2,4-dinitrophenylhydrazine but no precipitate with alkaline aqueous

iodine?

A B $ C 5 D 6[.JC / MCQ / Q2]

[.JC H1 / MCQ / Q2]

26 0ldeh"des can undergo addition reactions with a !ariet" of comounds of the form --

according to the following equation.

C /

-

G --c a t a ly s t

C-

/-

-

0n examle of such a reaction is the formation of c"anoh"drin, where-4 CN.

Which of the following comounds cannot be obtained b" such an addition reaction to

aldeh"de, followed b" deh"dration&

A B

C D

[6JC H2 2011 / Q2]


43/88

*arbon(l *ompounds

28 The Wittig reaction in!ol!es the reaction of a carbon"l comound with a hoshorus "lide to

gi!e an alene. The reaction occurs because of an imortant oxahoshetane intermediate.

Which one of the following structures shows the roduct of the reaction between the following

comound and the hoshorus "lide shown&

A

B

C

D

[I H2 2011 / Q2$ 2]

29 utanone, C-C-2C/C- , ma" be used as the starting oint for s"nthesi%ing Comound ,

C-C- 4 C'C//-)C- . Which is best rocess for roducing comound &

A C-C-2C/C- C-C-2C'/-)2C- C-C-2C'/-)'CN)C-

B C-C-2C/C- C-C-2C'/-)'CN)C- C- C- 4 C'CN)C-

C C-C-2C/C- C-C-2C-'/-)C- C- C- 4 C'CN)C-

D C-C-2C/C- C- C- 4 C '/-)C- C- C- 4 C'CN)C-

[TPJC / MCQ / Q22]

[TPJC H1 / MCQ / Q22]


44/88

*arbon(l *ompounds

+or each of the following questions, one or more of the three numbered statements 1 to 3ma"

be correct. 7ecide whether each of the statements is or is not correct. The resonses A to D

should be selected on the basis of:

A B C D

1, 2and 3

are correct

1and 2onl"

are correct

2and 3onl"

are correct

1onl" is

correct

1 A synthesis pathway, with/ and as the intermediates, is shown below:

Which of the following statements are true about the s"nthesis&

1 te I is a nucleohilic addition reaction.

2 te II is an electrohilic substitution reaction..3 te III is a reduction reaction.

[.JC / MCQ / Q40]

2 Which of the following statements are true for comound A&

1 (t gi!es a orange reciitate with 2,$#dinitrohen"lh"dra%ine.

2 (t gi!es a sil!er reciitate with TollensJ reagent.

3 (t undergoes esterification with henol.

[AJC / MCQ / Q39]

The comound " C-C/C-2C-/, was reacted in searate exeriments with:

'i) 2,$#dinitrohen"lh"dra%ine 'ii) alaline aqueous iodine

'iii) TollenHs reagent A0g'N-)2BG'aq)

Which statements about these reactions are correct& /ne mole of "could

1 react with two moles of 2,$#dinitrohen"lh"dra%ine in 'i).

2 form one mole of C-(in 'ii).

3form one mole of C-C/C-2C//- in 'iii). [ACJC / MCQ / Q40]

$ afranal is a comonent of the "ellow d"estuff saffron.

Which one of the following descritions about safranal isKare correct&

1 (t gi!es an orange reciitate with 2,$#dinitrohen"lh"dra%ine.

2 (t does not react with +ehlingJs solution.

3 0ll atoms in the molecule lie in one lane.

[N6JC / MCQ / Q39]


45/88

*arbon(l *ompounds

5 The following comound6 is a fla!ouring agent in food.Which of the following statement is not true&

1 Comound6 will gi!e bric red reciitate with +ehlingJs solution.

2 Comound6 will gi!e "ellow reciitate with aqueous alaline

iodine.

3 Comound6 will decolourise an acidified solution of otassiummanganate'I(()..

[PJC H1 / MCQ / Q30]

6 Which of the following tests can be used to distinguish between the two organic compounds

below?

1 Na metal2 aqueous bromine

3 acidified ;n/$ [.JC H1 / MCQ / Q29]

8 Two female sex hormones are oestrone and oestradiol.

/C-

/-

/-C-

/-

oestrone oestradiolWhich of the following reagents could notbe used to distinguish between the two hormones&

1 +ehlingJs solution

2 (2in Na/- 'aq)

3 odium metal

[6JC H1 / MCQ / Q30]


46/88

*arbon(l *ompounds


1 0nother commonl" used oxidising agent for organic reactions is otassium manganate'I((),

;n/$.

'i) 7raw the full structural formula of the organic roduct that is formed when acidified otassium

manganate'I(() is added searatel" to comounds A and B.

'ii) 7escribe a reaction b" which "ou could distinguish between A and B. tate the reagents,

conditions and the obser!ations "ou can mae with 'ac@ comound.

'iii)Comound B reacts with h"drogen c"anide. tate the t"e of reaction and the conditions

necessar" for this reaction to tae lace&

'i!)7raw the structure of the organic roduct that is formed.

[AJC H1 / IIB / Q c ( ]

2 Comound Bis a etone which has the formula C$-9/.

'i) (t gi!es a ositi!e triiodomethane test. 7raw the structure of the grou resent in B.

'ii) =i!e the structure of the roduct Cobtained in the triiodomethane test.

(2 G Na/-'aq)

B CHI3 C

'iii) 7educe the structure of Busing the a!ailable information from 'i) and 'ii).

'i!)7escribe the use of 2,$#dinitrohen"lh"dra%ine with B.

'!) Comound Bcan undergo further reaction as shown in the scheme.

B D

/Cl2, reflux

E-2

=i!e the structural formula for Dand E.

[ACJC H1 / IIB / Q1B a - c ]

Comound F Comound ?

tate how comound ? can be s"nthesi%ed from Comound F.

?our answer should include the *nt'%7'(*at' co7o&n('s) formed in each ste and the

%'a'nt) an( con(*t*on) required in each ste's).

[MI H1 / IIB / Q1 - ]


47/88

*arbon(l *ompounds

$ *innamaldeh(de, acet(lh(dro#uinone and vanillin are three common carbon"l comound

deri!ati!es used in industr".

'a)@sing cinnamaldeh(de as the starting material, state suitable reagents and conditions to carr"

out the following t"e of reaction.

'i) addition reaction of the aldeh"de grou

'ii) oxidation of onl( the alene grou

'iii)oxidation of onl( the aldeh"de grou+or each reaction, draw the structural formula of the organic roduct.

'b)

'i) oth acet(lh(dro#uinone and vanillin react with 2,$#dinitrohen"lh"dra%ine. =i!e the

obser!ation exected and write a balanced equation for the reaction of acet(lh(dro#uinone

with 2,$#dinitrohen"lh"dra%ine.

'ii) 7escribe a simle chemical test each to distinguish acet(lh(dro#uinone from vanillin. tate the

reagent and condition, and describe what would be seen with each comound.

[MJC H1 / IIB / Q# a - ]

5 C"clohexanone can be con!erted to c"clohexanamine, in stes as shown below. =i!e thereagents and conditions for stes 1 to 3 and draw the structures for A and B in the boxes

ro!ided.

St' 1 St' 2

[N6JC / II / Q# ]

6 Use the information below to identify the compounds to>. Explain your reasoning.

and, each has the molecular formula C4H8O. Both produce an orange precipitate with

2,4-dinitrophenylhydrazine but only reacts with an alkaline solution of iodine.

[.JC H1 / IIB / Q$ a ** ]

N-2A B/

St' 3


48/88

*arbon(l *ompounds

8 The following data is related to an organic substance .

h"sical state at r.t.. Liquid

;olecular formula C$-6/

Chemical test Eeagent Eesults

0 2,$#dinitrohen"lh"dra%ine /range reciitate

TollenJs reagent No reaction

C romine water 7ecolourised

'a) What are the conclusions that can be made about the structure of b" considering:

'i) test 0 alone 'ii) test 0 and together 'iii) test C alone

'b) uggest a ossible structure of .

[6JC H1 / IIA / Q2 a -]

9 (burofen was disco!ered b" oots harmaceuticals in the late 1s and was used to treatarthritis and similar roblems. (t has now become the third largest selling analgesic after

aracetamol and asirin. The first ste in the manufacturing rocess is the con!ersion of 2#

meth"l#1#hen"l#roane, nown as IBB'this is short for its common name, *so-ut"l-en%ene),

into the comound nown as (0, shown in the following reaction sequence:

(n the second stage of the industrial s"nthesis of iburofen, IBAP is con!erted into the

intermediate comound A, whose structural formula is shown below. This then undergoes

se!eral further reactions to roduce iburofen.

'a) tate the functional grou resent in IBB:

'b) What is the t"e of reaction that IBBhas undergone&

'c) 7escribe a simle chemical test to distinguish between IBBand IBAP, gi!ing the reagents and

conditions, obser!ations, and balanced equations for the ositi!e test.

C C C-

C-

-

-

-

C C C-

C-

-

-

-

C/ C-

C-

C

/

Cl

IBBIBAP

C C C-

C-

-

-

-

C CC-

/

-

-

e!eral stes

C C C-

C-

-

-

-

C CC-

/

/-

-

Comound A (burofen

+

0lCl


49/88

*arbon(l *ompounds

'd) Name the functional grou which is resent in comound A, but not in IBBor IBAP.

'e) uggest reagents and conditions that can be used to con!ert comound Ato (burofen in one

ste in the laborator"&

'f) uggest a reason wh" this method is not used in the actual industrial rocess to s"nthesi%e

(burofen.

'g) Comlete the reaction scheme below with comound Aas the starting material. 7raw thestructural formula of the o%an*c %o(&ct)formed, or gi!e a suitable reagent and conditions 'if

an"), in each of the boxes ro!ided.

[6JC H1 / IIA / Q ]

C C C-

C-

-

-

-

C CC-

/

-

-

Comound A

C C C-

C-

-

-

-

C CC-

/

-

-

.r

C C C-

C-

-

-

-

C CC-

/

-

-

r

or

TollenJsreagent,

heat

+*,

+**,

+***,

-CN, Na/-'aq)P 1>MC 3 2> MC


50/88

*arbon(l *ompounds

E))a Q&')t*on)

1 ;r densit"Kg cm solubilit" in water

roanone 59.> >.8< miscibleethanoic acid 6>.> 1.>5 full" miscible

'a)*xlain the differences in densit" and solubilit" in water for roanone and ethanoic acid.

'b) =i!e a detailed descrition of the mechanism reaction between roanone and h"drogen

c"anide.

[ACJC / III / Q4 - c ]

2 Comound P can be s"nthesised from cinnamaldeh"de.

Comound P cinnamaldeh"de

'i) uggest a s"nthetic athwa" for the formation of Comound P from cinnamaldeh"de. uggest

aroriate reagents and conditions as well as structures of an" intermediates formed.

'ii) =i!e the structural formula of the organic roducts formed when Comound P is refluxed with

acidified otassium manganite .

'iii) Comound P is able to rotate the lane of olarised light due to the resence of the chiral

carbon atom. *xlain wh" Comound Ps"nthesised from cinnamaldeh"de in art 'i) does not

exhibit this

beha!iour.

[IJC / III / Q2 a ** *** *5 ]

anillin and acet(lh(dro#uinone are two commonl" used carbon"l

comound deri!ati!es used in industr". The largest single use of vanillin

is as a fla!oring, usuall" in sweet foods such as ice cream and

chocolate while acet(lh(dro#uinone is used in de!eloing hotograhic

emulsions. oth comounds exists as "ellow solids that are soluble in

water to form a "ellow solution which is ercetible e!en at minute

concentrations.

'a) oth organic comounds react with h"droc"anic acid, -CN at different rates. This reaction

requires an amount of a base such as sodium h"droxide to be added.

'i) Name and describe the mechanism between -CN and acet(lh(dro#uinone. *xlain clearl" the

role of the base in this reaction.

'ii) (n the reaction of vanillin with -CN, onl" a small amount of a base is required. uggest wh" for

acet(lh(dro#uinone, more sodium h"droxide is required for an" significant reaction to occur.

'b)

'i) oth vanillin and acet(lh(dro#uinone reacts with 2,$#dinitrohen"lh"dra%ine. =i!e the

obser!ation exected and write an equation for the reaction with acet(lh(dro#uinone.


51/88

*arbon(l *ompounds

'ii) =i!e one ositi!e chemical test 'ac@, for vanillin and acet(lh(dro#uinone, which will allow the

two comounds to be distinguished from one another. tate the reagents, conditions and

obser!ations exected.

[MJC / III / Q2 a - ]

$ Three unlabeled reagent bottles are nown to be containing three comounds below."

C

/

C-2 C-2/-

6

C

/

C- /-

C-

C C-2 C

/-

-

/

-

'i) uggest how the identit" of the comound in each bottle can be identified b" simle chemical

tests. ?our answer should state clearl" the reagents and conditions used for the test and theobser!ations of the reactions that allow "ou to reach "our conclusion

'ii) What t"e of reaction is undergone when comound F reacts with h"drogen c"anide

and trace amount of Na/-& tate the conditions necessar" for the reaction to tae lace.

'iii) riefl" describe the stes in the mechanism of this reaction.

[N6JC / III / Q4 ( ]

5 *hloral h(drateis an unstable drug that can decomose easil" to form chloral

with a loss of water molecule. *hloral reacts with cold alaline h"drogen

c"anide under aroriate conditions to "ield comound B.

'i) 7raw the disla"ed formula for comound B.'ii) /utline the mechanism for the reaction of chloralwith h"drogen c"anide.

[TPJC / III / Q4 a ** ]

6 roose a reaction s"nthesis route for the following con!ersion:

C-

C

C-

C

-

C C-2

-

C-

C C CC-

C--

/- -

/

'tate reagents and conditions, and show all intermediates)

[6JC / III / Q4 a ]

8 quaric acid is an unusual organic comound with molecular formula, C$-2/$, and its s"stematic name

is 1,23dih"drox"c"clobutene#,$#dione. uggest what "ou would exect to see when squaric acid

reacts with :

'a) 2,$#dinitrohen"lh"dra%ine agent

'b) hoshorus entachloride.

=i!e equations for the reactions that occurred.

[6JC / III / Q a * c]

Chloral h"drate


52/88

6$ Car.o+ lic %ci*s an*

*arbo+(lic Acids

1 Which of the following air of comounds would roduce the same carbox"lic acid uonh"drol"sis&

A C-C-2C/Cl C-C/2C-B C-C-2CN C-C/2C-2C-C C-C-2CN C-C-2C/2C-D C6-5C/N-2 C6-5N-C/C-

[AJC / MCQ / Q2#]2 utanoic acid can be obtained from the following reactions '?c't

A refluxing C-C-2C-2C-2/- with 2Cr2/8K -G

B refluxing C-C-2C-2C-2CN with dilute -2/$C refluxing C-C-2C-2C-/ with A0g'N-)2B

G,followed b" acidificationD refluxing C-C-2C-2C//C-with dilute -2/$

[IJC H1 / MCQ / Q19]

The diagram below shows the s"nthesis of Comound S starting from ben%ene.

Which one of the following gi!es the correct t"es of reactions for ste 1 to 3&

A

B

C

D

$ Comound . is formed from ethanal !ia a series of reactions below.Which of the following reactions is not reresented in the sequence&A nucleohilic addition B electrohilic addition

C h"drol"sis D condensation

[HCI / MCQ / Q24]

5 Which of the following comounds reacts with Cl5 at room temerature to roduce anorganic comound that reacts !igorousl" with water&

A C-C//- B C-C//C- C C-C-2C-2/- D -/C-2C-2/-[ACJC / MCQ / Q29]


53/88

*arbo+(lic Acids

6 The structure of an organic comound . is as shown:Which one of the following statements is true&A The six#membered carbon ring in . is lanar.B . reacts readil" with cold -CN under acidic conditions.C . changes warm acidified aqueous otassium dichromate from orange to green.D Eeaction of sodium carbonate with . roduces a gas which forms a white reciitate with

calcium h"droxide. [HCI H1 / MCQ / Q19]

8 0 mixture is made b" mixing excess aqueous sodium carbonate with hen"lmethanol,henol and methanoic acid. Which organic secies isKare resent in the organic la"er of thesolution&A hen"lmethanol B methanoic acidC hen"lmethanol and henol D hen"lmethanol, henol and methanoic acid

[IJC / MCQ / Q2#]

9 The following comound, Iitamin C is soluble in water.Which one of the following statements is correct&A The molecule is lanar.B (t can exist as cis#trans isomers.C (t can react with hot sodium h"droxide.D (t can react with 2,$#dinitrohen"lh"dra%ine to form a bright orange reciitate.

[MI H1 / MCQ / Q20]

< Which one of the following comounds is not reduced b" Li0l-$&A C6-5C//- B C-C/C- C C-24C-2 D C-C-/


1> -ow man" moles of -2react with one mole of the following comound&A 2 B C $ D 5

[NJC / MCQ / Q23]

11 Citric acid, which causes the shar taste of lemon Suice, has the following formula. Which of the following reacts comletel" with 1 mole of citric acid&

A moles of Cl5 B moles of Na-C/

C $ moles of -Cl

D $ moles of Na/-

[PJC H1 / MCQ / Q24]

12 When an organic comound " was treated with hoshorous entachloride, fumes of -Clwere e!ol!ed. When "was warmed with acidified concentrated otassium manganate 'I((),the solution turned colourless from urle.A C-C-2C-/ B C-C/C- C 'C-)C/- D C6-5C-4C-C/2-

[TPJC H1 / MCQ / Q1]

1 0 comound P reacts with Cl$ to form h"drogen chloride gas and decolourises hotacidified otassium manganate'I((). Which of the following could Pbe&


54/88

*arbo+(lic Acids

AC C

/

/-

/

/-

BC-

C

-

/

CC-

C

C-

/

D

C-

C C-

C-

/-

[6JC / MCQ / Q2$]

1$ Which one of the following pairs of substances react together to form an organic product that

gives a neutral solution?

% C6H5OH and Na ( C6H5NH2and HCl

C C6H5CH2CH(NH2)COOH and HCl ) C6H5COCH3and LiAlH4[.JC / MCQ / Q2#]

15 Which one of the following gi!es the correct order of acid strength 'strongest first) forroanoic acid, 2#chlororoanoic acid, and #chlororoanoic acid&

strongest weaestA C-2ClC-2C/2- C-C-ClC/2- C-C-2C/2-B C-C-ClC/2- C-2ClC-2C/2- C-C-2C/2-C C-C-ClC/2- C-C-2C/2- C-2ClC-2C/2-D C-C-2C/2- C-C-ClC/2- C-2ClC-2C/2-


16 Wh" is chloroethanoic acid, CIC-2C/2-, a stronger acid than ethanoic acid&

A Chlorine releases electrons and destabili%es the CIC-2C/2#anion.B Chlorine releases electrons and stabili%es the CIC-2C/2

#anion.C Chlorine withdraws electrons and destabili%es the CIC-2C/2

#anion.D Chlorine withdraws electrons and stabili%es the CIC-2C/2

#anion.[MI H1 / MCQ / Q19]

18 Which sequence shows the following comounds in order of increasing acidit"&(ncreasing acidit"

A C6-5C-2C/2- C6-5/- C6-5C/2- C6-5C-2C-2/-B C6-5C-2C-2/- C6-5/- C6-5C-2C/2- C6-5C/2-

C C6-5C-2C-2/- C6-5/- C6-5C/2- C6-5C-2C/2-D C6-5C/2- C6-5C-2C/2- C6-5/- C6-5C-2C-2/-

[N6JC / MCQ / Q2$]19 Which of the following shows the correct order of increasing a&

A ", !,6, B !, ",6, C ,6, !, " D , !,6, "[HCI / MCQ / Q30]

1< 0rrange the following comounds in ascending 'from smallest to largest) order of a.

C-C-'I)C//- C-C-2C//- C-C-'Cl)C//- C-C-'+)C//- 'i) 'ii) 'iii) 'i!)


55/88

*arbo+(lic Acids

A 'i!), 'iii), 'i), 'ii) B 'ii), 'i), 'iii), 'i!) C 'i), 'iii), 'i!), 'ii) D 'ii), 'i!), 'iii), 'i)[IJC / MCQ / Q1$]

2> henol has a aof 5.8.Which one of the following has a lower a!alue&A 'C-)CC//- B 2,$,6#trimeth"lhenol

C D

[NJC / MCQ / Q24]21 (n which sequence does the !alue of a decrease continuousl"&A C-C/2- O CClC/2- O C2-5/- O C6-5/-B CClC/2- O C-C/2- O C2-5/- O C6-5/-C C2-5/- O C6-5/- O C-C/2- O CClC/2-D C6-5/- O C2-5/- O C-C/2- O CClC/2- [PJC / MCQ / Q2]

22 Which sequence shows the correct order of ('c%'a)*na!alue&A C-C-2/- O C-C/Cl O C-C/2-B C-C/2- O C6-5/- O C-C-2/-C C6-5/- O C-C/2- O C6-5C/2-D C-C/Cl O C-C/2- O C6-5/-

[TPJC / MCQ / Q30]

2 Which of the following, in aqueous solutions of equal concentration, has the lowest -&

A chloroethanoic acid B ethanoic acidC roan#1#ol D 2#chlororoan#1#ol[6JC H1 / MCQ / Q23]

2$ Three halogeno comounds can be s"nthesised from an organic comound b" thefollowing routes:

When comounds , ;, M and N 'not necessaril" in that order) are added to searateortions of water, solutions are formed with - !alues of >.5, 2.5, .> and .5.7educe which - !alue is associated with each of , ;, M and N. [MJC / MCQ /

Q22]

ABC

D25 romine#containing organic comounds can be h"drol"sed

under suitable conditions to roduce the corresondingbromide ion, r#, which then can be reacted with aqueous


56/88

*arbo+(lic Acids

sil!er nitrate to form a cream reciitate.0 student in!estigated the mass roduced b"h"drol"sing $ different bromine containing comounds,! " 6 =Which of the following gi!es the correct structuresfor ! " 6 &

ABCD

[MJC / MCQ / Q24]

26 Which sequence shows the'rong order of increasing ease of hydrolysis?

% C6H5Br < C6H5CH2Cl < CH3CH2COCl < CH3CH2*

( C6H5CH2Cl < C6H5CH2Br < CH3CH2* < CH3CH2COCl

C C6H5Cl < CH3COCH2Cl < C6H5CH2Br < CH3CH2*

) C6H5Br < CH3CH2Cl < C6H5CH2* < CH3CH2COCl[.JC / MCQ / Q2$]

28 Which materials are best used for the s"nthesis ofthe following comound&A C-C//- and C-N-2 B C-C/N-2and C-r

C C-C/Cl and C-N-2D C-C/N-2and C-/-

[ACJC / MCQ / Q30]

29 2#h"drox"butanoic acid, C-C-2C-'/-)C/2- is treated with hoshorus entachloride andthe organic roduct after isolation is added to cold water.Which of the following is the formula of the main organic roduct obtained&A C-C-2C-'/-)C/Cl B C-C-2C-ClC/2-C C-C-2C-ClC/Cl D C-C-2C-'/-)C/2-


2< 7euterium, 7, is an isotoe of h"drogen. Which of the following#ste s"ntheses will ro!ide comound A in good "ield&

-C

C

/

N

C-

-


57/88

*arbo+(lic Acids

A B

C D

[MJC / MCQ / Q30]

> *th"l butanoate is used to mae s"nthetic ineale fla!our.

C-C-2C-2C/2C2-5eth"l butanoate

Which set of reagents could be used to reare eth"l butanoate in the laborator"&A C-C-2C-2C-2Cl, C-C/2-, -2/$ B C-C-2C-2C-2/-, C2-5Cl, -2/$C C-C-2C-2/- , C2-5C/2-, -2/$ D C-C-2C-2C/2-, C2-5/-, -2/$

[AJC H1 / MCQ / Q23]

1 Which of the following sets of starting materials ma" be used for the rearation of hen"lben%oate in the laborator"&A C6-5/-, C6-5C//-, -2/$'l) B C6-5Cl, C6-5C/ClC C6-5/-, C6-5C/Cl, Na/-'aq) D C6-5Cl, C6-5C/Cl, Na/-'aq)

[TPJC / MCQ / Q23]

2 (soent"l acetate, C-C/2C-2C-2C-'C-)2is reared b" reacting an excess of ethanoicacid with isoent"l alcohol in the resence of sulfuric acid.

C-C/2C-2C-2C-'C-)2'C-)2C-C-2C-2/- C-C//-G G -2/

The method to obtain the roduct, isoent"l acetate, would in!ol!e(: adding anh"drous sodium sulfate((: distillation(((: searation of liquids using a searating funnel(I: shaing the mixture with Na-C/

[DHS H2 2011 / Q29]

0 comound , with molecular formula C/2, is heated under reflux with aqueous sodiumh"droxide and the resulting mixture then cooled and acidified with dilute sulhuric acid. The

A (, ((, ((( B ((, (((, (I

C (, ((, (I D (, ((, (((, (I


58/88

*arbo+(lic Acids

final roducts include a comound that turns blue litmus solution red, and another whichgi!es a urle colouration when tested with aqueous iron'((() chloride. What could be&

A C6-5/C/C-2C- B C6-5C-2/C/C- C C6-5/C-2C/C- D C6-5C-2C-2C//-

$ When eth"l ethanoate undergoes h"drol"sis with dilute sulhuric acid in the resence of

-219/, a mixture of two roducts is formed. Which of the following airs correctl" gi!es thestructures of the two roducts&A C-C/

19/- and C-C-219/- B C-C//- and C-C-2

19/-C C-C

19//- and C-C-2/- D C-C/19/- and C-C-2/-

[N6JC H1 / MCQ / Q23]

5 Which of the following substances will "ield an alcohol uon being heated under reflux withaqueous sodium h"droxide&A C-C-2N-2 B C-C-2C/2C- C C-C-4C- D C6-5r

[TJC / MCQ / Q23]

6 Which one of the following is formed when the comound .is refluxed with an excess ofaqueous alali&

comound .A C6-5C/2

3and 3/C6-$C/23 C C6-5/

3and 3/C6-$C/23

B C6-5C/23and -/3C6-$C/2- D C6-5/- and -/2C3C6-$CXN

[IJC 2011 / MCQ / Q2]

8 What are the roducts formed when comound J

/C/C-C-/C/

is heatedwith dilute sulhuric acid&

A /--/

and C-C/2-

B C/2--/2Cand C-/-

CC-C-2/- ,

C/2--/

and -C/2-

DC-/-,

/--/2C

and C-C/2-[SJC H1 / MCQ / Q24]


59/88

*arbo+(lic Acids

9 Comound6is boiled with aqueous sodium h"droxide and the resulting mixture cooled andacidified with dilute sulhuric acid. The final roducts include a comound C -6/2and analcohol. This alcohol gi!es a ositi!e iodoform test. What is the formula for comound6&A C-C-2C/2C- B C-C-2 /C/C-C C-C-2C/2C-2C- D -/C-2C-2 C/2C-2C- [TPJC / MCQ / Q24]

< Which of the following statements is correct with regards to the con!ersion of comound Bto comound D&

A The con!ersion in!ol!es, in sequential order, an elimination reaction followed b" anesterification reaction.

B The con!ersion in!ol!es, in sequential order, a substitution reaction followed b" anaddition reaction.

C The first ste must consist of the con!ersion of comound B into an alene.D The second ste requires the use of ethanoic acid. [MJC H1 / MCQ / Q23]

$> *(fluthrin is a s"nthetic "rethroid insecticide that has bothcontact and stomach oison action. (t is a non#s"stemic chemical used to control ants, cocroaches,mosquitoes and man" others.What are the liel" organic roducts from the reaction of

c(fluthrin with an excess of boiling aqueous Na/-&

A

B

C

D

[MJC / MCQ / Q2]


60/88

*arbo+(lic Acids

+or each of the following questions, one or more of the three numbered statements 1 to 3ma"be correct. 7ecide whether each of the statements is or is not correct. The resonsesA to Dshould be selected on the basis of:

A B C D

1, 2and 3

are correct

1and 2onl"

are correct

2and 3onl"

are correct

1onl" is

correct

1 (n which of the following two#stage s"ntheses could a nitrile be the intermediate '",6 or ) &

1 C-C-2C-2r " C-C-2C-2C//-

2 C-C-2C-2C-2/- 6 C-C-2C-2C-2C-2/-

3 C-C-2( C-C-2N-2 [N6JC / MCQ / Q3$]

2 Which of the reagentKs added will roduce similar obser!ation when added to these two

comounds&

1 Cl5 2 Na 3 0cidified ;n/$K reflux[MI H1 / MCQ / Q29]

Which of the following statements isKare t%&'for -/C-2C/2- and -2NC-2C/2-&

1 oth react with aqueous sodium h"droxide.2 oth form %witterions.3 oth are insoluble in water.

[TJC / MCQ / Q3$]

$ ;alic acid, -/2CC-'/-)C-2C/2-, is found in some fruits. Which roerties does malicacid ha!e&1 (ts molecule contains a rimar" alcohol grou.2 (t can form esters with both ethanoic acid and with ethanol.3 1 mole of malic acid will react comletel" with moles of sodium metal.

[TJC H1 / MCQ / Q30]5 Comound> is found in bananas and comound H in ears.

Which statements are correct&1 > and H are structural isomers.2 > and H can be h"drol"sed in acidic and basic medium.3 > and H ha!e identical h"sical roerties.



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*arbo+(lic Acids

6 (n which of the following airs is the 2aof the first comound greater than the 2aof thesecond comound&

1 C-C-2C//-and C-C-2/-

2

C-C-C//-

Cl

and C-C-2C//-3 C-C-2C-2C//- and C-C-2C//-

[SJC H1 / MCQ / Q30]

8 Which of the following correctl" lists the comounds in order of decreasing acidit"&1 COOH

, C-CCl2C//-, C-C-ClC//-, C-C-2C//-

2

OH

%O2

&OH

&

CH3

OH&

OH

3 CH3

OH &

OH &

OH

Cl

&OH

[SJC / MCQ / Q39]

9 0n unnown comound is refluxed with aqueous sodium h"droxide solution. The roduct isacidified with nitric acid and aqueous sil!er nitrate solution is added. 0 reciitate isobser!ed. Which of the following could be the comound&1 C-C-2C/Cl 2 C-2rC/2- 3 C-I


< Which of the following will "ield an organic comound containing deuterium& '7 4 2-)1 2 3

[NJC / MCQ / Q40]

1> ",6and are three different three#carbon comounds. "and6react together to form anester. "and also react to gi!e the ester as " and6but much less readil". Comound "could be

1 roan#2#ol 2 roanoic acid 3 roano"l chloride[6JC / MCQ / Q39]


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*arbo+(lic Acids

11 en%ocaine and menthol are local anaesthetics used in sunburn ointments

and sin lotions. Their structures areshown below. Which of the followingreagents and conditions can be used todistinguish between these two

comounds&1 0queous bromine in the dar2 *thano"l chloride at room temerature3 -ot acidified aqueous otassium manganate(#II)

[PJC / MCQ / Q3]

12 Which of the following statements are true for the comound below&1 (t is a non#lanar comound.2 When boiled with aqueous sodium h"droxide, it is con!erted to

3 (t will react with 2,$#dinitrohen"lh"dra%ine at room temerature.[PJC / MCQ / Q39]

1 Fluorescein reacts with bromine to form 4, 5dibromofluorescein which

gives lipstick an orange colour. The structure of 4, 5dibromofluorescein

is show below. Which of the following statements are true for

4, 5dibromofluorescein?

1 It is likely to be hydrolysed by dilute hydrochloric acid.

2 It exhibits optical isomerism.

& It undergoes nucleophilic substitution with aqueous sodium hydroxide.

[.JC / MCQ / Q3]

1$ What would be the products formed when the following compound is

boiled with aqueous sodium hydroxide?

1 CH3CH2OH

2 CH3CH2O-Na+

3 ClCH2CH2COO-Na+

[.JC H1 / MCQ / Q30]


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*arbo+(lic Acids


1 C-'C-)2CN can be con!erted to 2#meth"lroanoic acid.'a) tate the reagents and conditions for the con!ersion.'b) Which is a stronger acid& 2#meth"lroanoic acid or 2#chlororoanoic acid& Wh"&

'c) 7escribe a simle chemical test to differentiate 2#chlororoanoic acid and 2#chloroben%oicacid.

[MI / II / Q$ ]

2 Tartrate ion is the conjugate base of the organic acid tartaric acid, that is used in

vinegar.

'i)When tartaric acid is heated in the presence of hot concentrated sulphuric

acid, two different organic products% and( of molecular formula C4H2O4

and C8H8O10are formed.

Suggest the structural formula for products% and(.

(ii)State and describe the two types of hybridisation present in the C atom of the tartaric acid

molecule.

[MJC / II / Q3 ( *5 ]

uggest a chemical test to distinguish between thefollowing airs of organic comounds.

[NJC / II / Q3 c * ]

$ ;ethanol can be oxidi%ed to methanoic acid.'i) Write an equation for the oxidation of methanol to form methanoic acid.'ii) 7escribe and exlain how the acidities of methanol, methanoic acid and chloromethanoic

acid comare with each other.[N6JC / II / Q3 - ]

5 aracetamol is the acti!e drug ingredient used to relie!e headache, fe!er and flu. (t was firsts"nthesised from $#nitrohenol b" -armon Northro ;orse in 1989 and was commerciall"roduced and mareted in 1


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*arbo+(lic Acids

'b) uggest a reason for the lower melting oint of asirin as comared to $#nitrohenol.'c)7escribe one simle test#tube reaction "ou could use to distinguish asirin from

seudoehedrine. tate the reagents conditions and obser!ations that can be seen.[PJC / II / Q$ a ( ' ]

6 Comound6can be s"nthesi%ed from ethene in a 2#ste rocess as follows:

I II

C-24C-2 "

6'i) uggest reagents and conditions for stes Iand II.'ii) 7raw the (*):a'(formula for the intermediate ".

[SJC H1 / IIB / Q3 - ]

8 idocaineis a common local anesthetic drug used toicall" to relie!e itching, burning andain from sin inflammations.@sing simle molecules lie 2,6#dimeth"lhen"lamine, ammonia and chloroethane,lidocainecan be s"nthesi%ed as shown below.

'i) 7raw the structures of ! and in the boxes below.'ii) uggest the structure of lidocaine.'iii) 7o "ou foresee an" roblem in the s"nthesis of & (f "es, exlain wh".

[TJC / II / Q c ]

9 >.>25 mol of a h"drocarbon "was combusted comletel" to roduce $.$ g of carbon dioxidegas and 1.5 g of water.1 mol of" can react with 2 mol of h"drogen gas. When " reacted with acidified otassiummanganate'I((), the latter was decolourised and comound 6 C2-2/$, was formed as oneof its roducts. 6reacted with Na2C/

to gi!e a colourless, odourless and acidic gas. 6reacted with 2 mol of C-/- under suitable conditions to form C$-6/$.7etermine the molecular formula of the h"drocarbon ", suggest and exlain how "ou arri!eat the structures for ",6and .

C /

/

C-2C-2/ C

/

C-

N-2

C-

+

C-

N-C/C-2Cl

C-

N- G C-C-2Cl

? G Vheat in a sealedtube to gi!elidocaine

!

6

2

heat in a

sealed tube

(C%H)


65/88

*arbo+(lic Acids

[TJC H1 / IIB / Q# ( ] +erulic acid, which can be used as antioxidant, is found in seedsof lants such as wheat and rice. (t has the structure as shown:tate what "ou would obser!e and gi!e the structural formula ofthe organic roduct when ferulic acid reacts with the followingreagents: 0queous bromine, *thano"l chloride, -ot acidifiedotassium manganate'I(()

tate what "ou would obser!e and gi!e the structural formula of the organic roduct whenferulic acid reacts with the following reagents: Cl5

[TPJC / II / Q a ]

11 Use the information below to identify the compoundsH to. Explain your reasoning.

H and each has the molecular formula C2H4O2.H has an acrid (sharp) smell whereas

has a fruity aroma.H reacts instantaneously with cold aqueous sodium hydroxide but

reacts only when heated under reflux with aqueous alkali.

[.JC H1 / IIB / Q$ a *** ]

12 +erulic acid is an acti!e ingredient in the Chinese herb Y7angguiZ.(ts structure is gi!en below.AThe C-/ grou can be considered

relati!el" inertB'a) +erulic acid exists as a air of geometric isomers. 7raw diagrams

to illustrate these isomers'b) When gaseous h"drogen chloride is reacted with +erulic acid, the roducts exhibit a different

t"e of stereoisomerism.'i) Name and define the new t"e of stereoisomerism exhibited.'ii) 7raw diagrams to illustrate the isomerism "ou ha!e described in 'i).

'c) +erulic acid is obser!ed to be relati!el" soluble in water.'i) *xlain its solubilit" in water with the aid of a diagram.'ii) Will +erulic acid be more or less soluble in aqueous sodium h"droxide& =i!e "ourreasoning.

'd) 7raw the structures of the organic roducts formed when +erulic acid reacts with thefollowing reagents:'i) 0queous bromine'ii) Cold dilute manganate'I(() ions'iii) -ot acidified manganate'I(() ions'i!)Lithium aluminium h"dride'!) en%o"l chloride'!i) Thion"l chloride, /Cl2

[6JC / II / Q4 ]

C-C-

2C/

2- C-

C-C/

2-

Cl

C-C-

2C-

2/-

C//-C-/

-/

C//-C-/

-/


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*arbo+(lic Acids

E))a Q&')t*on)

1'i) *xlain the differences in a!alues between the comounds shown below.

'ii) The aof the acid, is $.9 where ? is a substituent. redict the

roduct's) formed when Cl2is added to in the resence of +eCl in thedar. *xlain "our answer.

[IJC / III / Q4 c ]

2 Na2C/ can be also be used to distinguish between carbox"lic acids and alcohols. -owe!er,this is not ossible for roanoic acid and 2#h"drox"roanoic acid since both are carbox"licacids.

'i) The melting oints of roanoic acid and 2#h"drox"roanoic acid are 321 oC and 5 oCresecti!el". *xlain the difference in the melting oints of these two acids.

'ii) uggest chemical reagents and the conditions to distinguish both the monobasic acids.7escribe "our obser!ations for both the acids. [PJC / III / Q2 c ]

'a) 8.9 g of ethanal reacts with 5.> g of h"drogen c"anide in the resence of a trace amount of

sodium c"anide at 1> 3 2> MC to gi!e 12.> g of 2#h"drox"roanenitrile.'i) Calculate the ercentage "ield of 2#h"drox"roanenitrile in this reaction.'ii) *xlain wh" 2#h"drox"roanenitrile has no effect on olarised light e!en though it contains

a chiral carbon.'iii) 4#-"drox" acids '0-0s) are naturall" occurring carbox"lic acids which are well#nown for

their use in the cosmetic industr". Lactic acid, -/C-'C-)C//-, is an 0-0 can be formedfrom 2#h"drox"roanenitrile. Write a balanced equation for this reaction, stating clearl" thereagents and conditions.

'b)uggest methods b" which the following comounds could be distinguished from each other

b" chemical tests.'i)

and

'ii)and

'c) tate and exlain the relati!e solubilit" of 2#aminoben%oic acid and $#aminoben%oic acid inwater.

N-C/C-2 /C/C-2

r Cl


67/88

*arbo+(lic Acids

2a7*no-'no*c ac*( 4a7*no-'no*c ac*( [SJC / III / Q4 ]

$'a) 0 lethal combination of the following three rescriti!e drugs simultaneousl" can causedeath. The" are chloral h(drate, acetaminophen and meprobamate. The structures ofthese three drugs are as shown:

C C

Cl

Cl

Cl

-

/-

/-

chloral h(drate

/-

N

-

/

C-

acetaminophen

N-2

/

/

/ N-2

/

meprobamateuggest chemical tests to identif" two of the abo!e drugs 'namel" acetaminophen andmeprobamate). ?ou must gi!e a o)*t*5'test for each drug stating obser!ations as wellas essential reagents and conditions.

'b) ?ou are gi!en the following scheme of reactions.

'i) 7raw the disla"ed formula of comound C.'ii) =i!e the s"nthetic route, in!ol!ing not more than three steps, from Ato B. (n "our answer,

suggest reagents and conditions in!ol!ed in each ste.

C//-N-2C//-

N-2

/-

C/2-

A

C-2/-

/-

BC

D

C/N-C-2C-

2/- /-

Cl5


68/88

*arbo+(lic Acids

'iii) uggest a reagent together with the condition, which can be used to modif" the chemicalstructure of comound D, to mae it water soluble.

[TPJC / III / Q4 a * - ]

5 Comound Acan absorb ultra!iolet ra"s and is used in the roduction of sin cream. (tsstructural formula is shown below:

C-/ C- C- C

/

/ C-2'C-2)C-

tate the reagents and conditions for the reaction in St' III.uggest the mechanism of St' I. [6JC / III / Q3 c *** ]

6 Comound "has the molecular formula C$-6/2. "reacts with h"drogen c"anide to form 6,C6-9/2N2. "also reacts with hot acidified otassium dichromate'I() solution to roduce ,C$-6/. 2.5> g of ';r4 1>2) was dissol!ed in 25> cm

of water. 25.> cmof the solution

required 2$.5> cmof >.1>> mol dm#of sodium h"droxide for comlete neutralisation.

'i) Calculate the number of moles of that will be neutralised b" one mole of sodiumh"droxide. -ence suggest one structural formula of ". (dentif" comounds6and .

'ii) 7raw one isomer of " that beha!es lie ". Label the isomer !.'iii) uggest on'simle chemical test that can used to distinguish "from !. tate the reagents,

reaction conditions and obser!ations.[6JC / III / Q (]

Comound A

/- C-/ C-/ C-/

C-/ C-4C-C//-Comound A

1. Na/-

2. C-(

St'4 II

St'4 I

St'4 III


69/88

7$ 3itro en

$itrogen *ompounds

1 0 nitrile " undergoes the following two reactions:

What would be roduced when the roducts from the two reactions are mixed together&A A C-C-2N-

GB A 3/2CC-B B A C-C-2N-GB A 3/2CC-2C-B

C C-C/N-C-2C- D C-C-2C/N-C-2C-[AJC / MCQ / Q2]

2 Neotame is an artificial sweetener made b" Nutraweet that isbetween 9,>>> and 1,>>> times sweeter than sucrose.Which of the following is true about neotame&A (t is oticall" inacti!e.B (t can exist as a %witterion in solution.C Two roducts are obtained uon heating with aqueous Na/-.D (t decolori%es aqueous bromine in the absence of light.

[IJC / MCQ / Q2]

With what reagent would hen"lamine and henol gi!e a similar reaction&A r2 B -Cl 'aq) C Na metal D Na/- 'aq)

[MI / MCQ / Q2]

$ 0sartame is a sweetener commonl" used in diet soft drins and is ro!ided as a tablecondiment.

0sartameWhat are roduced when asartame is heated with aqueous sulhuric acid&A B

C D

[MI / MCQ / Q30]


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$itrogen *ompounds

5 When aqueous bromine is added to a solution of hen"lamine, the colour of the brominedisaears. Which of the following statements is true&

A The mechanism is elec

organic c cccc cccc

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