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CONFIDEN TIAL 2 AS/AP R 2008/CHM301

PART A (20 MA RKS)1. Which of the following compounds undergoes dehydration to form only onecompound without any isomer?

A. CH 3CH 2CH(OH)CH3B. CH3CH2CH2CH2OHC. (CH3)2C(OH)CH 2CH 3D. CH 3CH(CH3)CH(OH)CH 3

2. Which of the following will react with methanol under suitable conditions?I ethanoic anhydrideII ethanoyi chlorideIII ethyl ethanoa teA. I and IIB. I and IIIC. II and IIID. I, II and III

3. Which of the following compo unds CANNOT be prepared in one step from ethanoyichloride?A. CH 3COCH 2CH 3B. CH 3CONHCH 3C. CH 3COOC 3H 7D. CH3COOH

4. The reaction that converts pentanol to pentanoic acid is calledA.B.C.D.

esterificationreductionoxidationhydrolysis

5. Wh ich of the following compounds will produce a carboxy lic acid on hydrolysis?I.IIIIIA.B.C.D.

CH3OHCH3CNCH3COCII and III and IIIHand IIII, II and II

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CON FIDENTIAL 3 AS/APR 2008/CHM301

6. W hich of the following is FALSE regarding propyl butanoate?A. It can react with Grignard reagent to form an alcohol.B. It is soluble in water.C. It is forme d by the reaction between propanol and butanoic acid.D. It can react with amm onia to produce an amide.

7. W hich of the following compound s will give a positive isocyanide test?A. PropanamideB. PropylamineC. PropanalD. Propanol

8. Wh ich of the following statements is TRUE concerning benzoyi chloride?I. It can react with amm onia to produce benzamide.II. It can be hydrolyzed to form benzoic acid.III. It can react with ethanol to form ethyl benzoate.A. II onlyB. I and IIC. I and IIID. I, II and III

9. The compo und with the highest pH when it is dissolved in water isA. CH3COCIB. CH3CH2OHC. CH3CH2NH2D. (CH3CO)2O

10. The reaction between benzaldehyde and an aqueous solution of sodium hydroxide iscalledA. Cannizzaro reactionB. iodoform reactionC. Aldol condensationD. oxidation

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CONFIDENTIAL 4 AS/APR 2008/CHM301

PART B (40 MAR KS)

QUESTION 1Draw the structural formulae for the following co mpound s:a) trimethylamineb) phenylethanonec) 4 - methy lbenzoyl chlorided) propyl butanoate

(4 marks)QUESTION 2Give the IUPAC nam es for the following compou nds:a)

0 0II II

/-C-o-C-CH,c)

d) O CH-I I |3CH3 C - N - C H 2 C H 3

(4 marks)

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CONFIDENTIAL AS/APR 2008/CHM301

QUESTION 3Draw the structures of the main organic product(s) formed in the following reactions:

U A H ,a)

b)

CH2COOH 4 - ^

O oCH 3 C O C CH 2C H 3

H2O

c)Oc ci + C 6 H 6 AICI,

(4 marks)

QUESTION 4Consider the following comp ounds:Compound ACompound BCompound CCompound D

CH3CH2COOHCH3CH2CH2OHCH3CH2CH2NH2CH3CH2COCI

Which of the above com pound(s):a) has/have a fishy smell?b) will react with sodium to release hydrogen gas?c) will react with pheno l to give an ester? (4 marks)

QUESTION 5Write the balanced equations for the reaction between phenylamine, C 6H 5NH2 and thefollowing reagents:a) CH3COCIb) excess CH 3CI (4 marks) Hak Cipta Universiti Teknologi MARA CONFIDENTIAL

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QUESTION 6Compound X has with the following structure:

CH 3C H 3 C H 2 _ C - H

OHa) What is the ILJPAC name for compound X?b) Give the class of compo und X.c) Compound X will react with hot acidified potassium man ganat(VII), KMnO 4.

i) W hat is the nam e of the reaction?ii) Give the structural formula for the organic product form ed. (4 marks)

QUESTION 7Draw the structures of the main organic product(s) formed in the following reactions:

a)

b)

c)

d)

COOH

CH3CH2CH 2MgCI

CH3CHCICH3

N O .

Zn OA

co2

NaOH(aq)

Sn

->- R+

W

T

cone HCI(4 marks)

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QUESTION 8Consider the following co mpo unds:

Compound V : CH 3COCH3Compound X : CH 3CH2CHO

Compound Y: CHO

Compound Z : CH3CH2OHIdentify the compound(s) that:a) will give yellow precipitate whe n heated with alkaline solution of iodine.b) will give a red precipitate whe n heated with Fehling solution .c) will release hydroge n chloride gas whe n treated with phosphorou s trichloride.

(4 marks)

QUESTION 9Consider the reaction scheme below: CH3COOH

H Compound BCompound A

Step 1SOCL

COOH Compound C

a) Name compound A.b) Draw the structural formulae for the compounds B and C.c) Give the reagen ts needed for Step 1 to occur.

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(4 marks)

CONFIDENTIAL

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QUESTION 10Consider the following co mpo unds:

EthanamideEthyl ethanoateEthylamineEthanoyl chloridea) Wh ich com pound(s) will react with nitrous acid to give

i) ethanoic acid?ii) ethanol?

b) Wh ich compound(s) will dissolve in water to givei) an acidic solution?ii) a basic solution? (4 marks)

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CONFIDEN TIAL 9 AS/AP R 2008/CHM301

PART C (40 MARKS)

QUESTION 1The reaction schem e below show s the various reactions of com pound S .

o H^ , _ reagent 2 f/ \\ II ICompound T ^ / / \ ^ C - N -O v^\s* \ /Compound R ^ ^ ^ ( ^ - c -OH ' Compound U

^ Compound WCompounds

a) Draw the structural formulae of compounds R, T and W . (3 marks)b) Identify reagent Z. (1 mark)c) Give the IUPAC name for the compound U.

(1 mark)d) Compound S can be converted to alcohol H.

i) Give the structural formula and IUPAC name for alcohol H.ii) W rite the balance d equation for the conve rsion of com poun d S to alcohol H.iii) Name the reaction that has occurred. (5 marks)


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Q U E S T I O N 2Compound X can be found naturally in certain food.

OI IHO-CH2CH2-C-CH3 Compound Xa) Name the functional group(s) present in compo und X. (1 mark)b) Draw the structural formulae of the organic product formed when compound X isreacted with the following reagents:

i)ii)iii)

KC NLiAIH4CH3COOH (3 marks)

c) Suggest a chem ical test to differentiate the following pair of compo unds:i) Compound Xand its isomer Y, CH 3CH(OH)COCH3.i i) Compound Xand its isomer Z, HO CH 2CH2CH2CHO (6 marks)

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QUESTION 3The reaction scheme below shows the various reaction of amide R.

HCH3N CH3Compound G

CH3COCICompound I

O H, - C - N ~CH3

AmideR

HCH 3 CH2NCH3

HCICompound J

a) Give the ILJPAC name of the fo l lowing compounds:i ) amide Ri i ) compound

b) Draw thestructura l fo rmulae for the fo l lowing products:

i ) Compound Ii i ) Compound Ji i i ) Compound H

c) Give thereagents needed for:i) Step 1i i) Step 2

Compound H

(2 marks)

(3 marks)

(2 marks)

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d) Compou nd S is an isomer of amide R and has the following structural formula:0 H

C H 3 C H 2 - C - N - H C o m po u nd sGive the formulae of the product(s) formed w hen co mpou nd S is heated with:i) P2O5ii) NaOH(aq) (3 marks)

QUESTION 4a) Draw the structural formulae of the organic products formed when propanal isreacted with:

i) lithium alum inum hydrideii) acidified potassium dichromateiii) 2,4,-dinitrophenyhydrazineiv) excess CH 3MgCI

(4 marks)b) Propanal can also react with aqueous sodium hydroxide.

i) Draw the structural formulae for the product form ed,ii) Nam e the reaction that has occu rred.

(2 marks)

c) With the help of a reaction schem e, show how the following compounds can beprepared from propanoic acid:i) propanoic anhydrideii) propene (4 marks)

END OF QUESTION PAPER


chm301 apr 08

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