aldehydes & ketones - karnatakakea.kar.nic.in/cet2014/vikasana/chemistry/day_14.pdf ·...
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Aldehydes & Ketones
Aldehydes are compounds having general formulaH
CR O R= H, CH 3, C2 H5, C6 H5, etc…
Slide 2Ketones are compounds having general formulaR C
O
R R=CH 3,C2H5, C6H5 etc...
H
CR O R= H, CH 3, C2 H5, C6 H5, etc…
IUPAC names of AldehydesFormula Common Name IUPAC NameHCHO Fomaldehyde MethanalCH3CHO Acetaldehyde Ethanal
Slide 3
CH3CHO Acetaldehyde EthanalCH3CH2CHO Propionaldehyde PropanalCH3CH2CH2CHO Butyraldehyde Butanal(CH3)2CHCHO Isobutyraldehyde 2-Methylpropanal
IUPAC names of AldehydesFormula Common Name IUPAC NameCH2=CH-CHO Acrolein Prop–2–enalCH3CH=CH-CHO Crotonaldehyde But-2-enal
Slide 4
CH3CH=CH-CHO Crotonaldehyde But-2-enalC6H5CH=CH-CHO Cinnamaldehyde 3-Phenylprop-2-enalC6H5CHO Benzaldehyde BenzaldehydeC6H4(OH)CHO Salicyaldehyde 2-Hydroxybenzaldehyde
IUPAC Names of KetonesFormula Common Name IUPAC NameCH3COCH3 Acetone PropanoneCH3COCH2CH3 Ethyl methyl ketone Butanone
Slide 5
CH3COCH2CH3 Ethyl methyl ketone ButanoneCH3CH2COCH2CH3 Diethyl ketone Pentan-3-oneCH3COCH2CH2CH3 Methyl propyl ketone Pentan-2-oneC6H5COCH3 Methyl phenyl ketone orAcetophenone 1-phenylethanoneC6H5COC6H5 Diphenyl ketone orBenzophenone Benzophenone
Structure of Carbonyl groupC O
Sp2 - hybridised
C O120o
120o
Slide 6The carbon- oxygen double bond is polarized due to higherelectro negativity of oxygen than carbon. C+-O-
C O
Sp2 - hybridised
C O120o
120o
C ONucleophile
Electrophile
Hence
From oxidation of primary and secondary alcoholsR C
H
OH
H
PCC
[O]R C
OH
H
OH R C
H
O +H2O
Slide 8
R C
H
OH
H
PCC
[O]R C
OH
H
OH R C
H
O +H2O
R-CH(OH)-R’ KMnO4/KOH R-CO-R’ + H2O
By dehydrogenation of alcoholsR C
H
OH
H
Copper
300oCR C
H
O + H2
Slide 9
R C
H
OH
H
Copper
300oCR C
H
O + H2
R-CH(OH)-R’ Cu/573K R-CO-R’ + H2O
From alkene by ozonolysisR CH CH2 + O3
Zn
H2OR C
H
O + CH2OCH2
OO
CH
O
R
Slide 10
R CH CH2 + O3Zn
H2OR C
H
O + CH2OCH2
OO
CH
O
R
From Acyl ChlorideR C
O
Cl R C
O
H + HClH2
Pd - BaSO4
140oC
By Rosenmund reduction
Slide 11R C
O
Cl R C
O
H + HClH2
Pd - BaSO4
140oC
From Nitrile by Stephen’s ReductionR C N
SnCl2
+HClR CH NH
H2O
H+R C
H
O + NH3
Slide 12
R C NSnCl2
+HClR CH NH
H2O
H+R C
H
O + NH3
Preparation of Benzaldehyde fromTolueneCH3 CrO2Cl2
CS2
CHO+H2O
Etard's Reaction
Slide 13
CH3 CrO2Cl2
CS2
CHO+H2O
Etard's Reaction
By Gattermann – Koch reaction.
Slide 14C6H6 + CO + HCl Anh AlCl3/CuCl C6H5CHO
Dry distillation of calium salts give aldehyde and ketones.Calcium formate – FormaldehydeCalcium formate and calcium acetate - AcetaldehydeCalcium formate and calcium benzoate - BenzaldehydeCalcium acetate - AcetoneCalcium benzoate - BenzophenoneCalcium benzoate and calcium acetate - AcetophenoneSlide 15
Dry distillation of calium salts give aldehyde and ketones.Calcium formate – FormaldehydeCalcium formate and calcium acetate - AcetaldehydeCalcium formate and calcium benzoate - BenzaldehydeCalcium acetate - AcetoneCalcium benzoate - BenzophenoneCalcium benzoate and calcium acetate - Acetophenone
From nitrile and Grignard reagentR C N R
-| Mg
+x R C
R'
N. Mgx2 H2O
H+R C O
R'
+ NH3
Dry
Ether+ Mg
X
OH
Slide 16
R C N R-| Mg
+x R C
R'
N. Mgx2 H2O
H+R C O
R'
+ NH3
Dry
Ether+ Mg
X
OHR-MgX + HCN dry ether R-CH=NMgX H2O/H+ R-CHO
Ketones from Acyl chloride and dialkylcadmium2 R' C
O
Cl + R2Cd 2 R' C
O
R + CdCl2
Slide 17
2 R' C
O
Cl + R2Cd 2 R' C
O
R + CdCl2
Aromatic ketones from Benzene by Friedel – CraftreactionR C
O
ClC R
O
+ HClAnhydrous
AlCl3
Slide 18
R C
O
ClC R
O
+ HClAnhydrous
AlCl3
• Physical state: HCHO – Gas, Up to C13 are liquids and higherones are solids.• Odour : Lower aldehydes have unpleasant odour where ashigher ones have pleasant odour.• Boiling points: These compounds have higher boiling pointsthan ethers and hydrocarbons due to dipole interactions butlower boiling points than that of alcohols due to the absenceof intermolecular hydrogen bonding.
Physical properties of Aldehydes and ketones
Slide 19
• Physical state: HCHO – Gas, Up to C13 are liquids and higherones are solids.• Odour : Lower aldehydes have unpleasant odour where ashigher ones have pleasant odour.• Boiling points: These compounds have higher boiling pointsthan ethers and hydrocarbons due to dipole interactions butlower boiling points than that of alcohols due to the absenceof intermolecular hydrogen bonding.
Reactions of Aldehydes and Ketones(i) Nucleophillic additiona
Cb
O
Planar
a
C
O
b
Nu
H+
a
C
OH
b
Nu
+ Nu
Tetrahedral intermediate Addition Product
slowfast
Slide 20
aC
bO
Planar
a
C
O
b
Nu
H+
a
C
OH
b
Nu
+ Nu
Tetrahedral intermediate Addition Product
slowfast
Reactions of Aldehydes and KetonesWith HCNBoth aldehydes and ketones react with HCN to form additionproduct Cynohydrin (in presence of a base)
HCN + OH- CN
- + H2O
C O
CNC
O
CN
H+
TetrahedralCyanohydrinIntermediate
COH
CN
Slide 21
HCN + OH- CN
- + H2O
C O
CNC
O
CN
H+
TetrahedralCyanohydrinIntermediate
COH
CN
Reactions of Aldehydes and KetonesWith NaHSO3
Bisulphite addition CompoundAll aldehydes react with NaHSO3 to form a white crystallinesolid, bisulphite addition compound. Many ketones also react.But acetophenone does not react with NaHSO3 due to stearichindrance.
C O
+ Na+ SO
-3 H C
O Na
SO3HC
OH
SO3Na
Proton Transfer
Slide 22
With NaHSO3
Bisulphite addition CompoundAll aldehydes react with NaHSO3 to form a white crystallinesolid, bisulphite addition compound. Many ketones also react.But acetophenone does not react with NaHSO3 due to stearichindrance.
C O
+ Na+ SO
-3 H C
O Na
SO3HC
OH
SO3Na
Proton Transfer
Reactions of Aldehydes and KetonesWith alcoholsOnly aldehydes react with alcohols in presence of dry HCl toform acetals.
Slide 23R C
H
Odry HCl
R C
HOR '
OR '+H2O2 R ' OH
acetal
Reactions of Aldehydes and KetonesWith alcoholsKetones react only with Ethylene Glycol to form cyclic product
C OR
R
CH2 OH
CH2 OH
RC
R
O
O
CH2
CH2
+H 2O
Ethylene Glycol Ketal
dry HCl
Slide 24
C OR
R
CH2 OH
CH2 OH
RC
R
O
O
CH2
CH2
+H 2O
Ethylene Glycol Ketal
dry HCl
Reactions of Aldehydes and KetonesWith ammonia derivativesWhere Z=OH, NH2, C6H5NH, NHCONH2 alkyl, aryl NH2 Z
Slide 25C O
NH2 Z COH
NH Z
C N Z +H2O
Reactions of Aldehydes and Ketones• NH2-NH2 CH3CH=N-NH2 Hydrozone• NH2-OH CH3CH=N-OH Oxime• NH2-NHC6H5 CH3CH=N-NHC6H5 Phenyl hydrozone• NH2NHCONH2 CH3CH=N-NHCONH2 Semicarbazone
Slide 26
• NH2-NH2 CH3CH=N-NH2 Hydrozone• NH2-OH CH3CH=N-OH Oxime• NH2-NHC6H5 CH3CH=N-NHC6H5 Phenyl hydrozone• NH2NHCONH2 CH3CH=N-NHCONH2 Semicarbazone
Reactions of Aldehydes and KetonesMechanism
COH
N - Z
H
C O
: NH2 Z CO
-
N
H
HZ
H+ Transfer
Unstable
COH
N Z
H
C N Z +H2O Slide 27
COH
N - Z
H
C O
: NH2 Z CO
-
N
H
HZ
H+ Transfer
Unstable
COH
N Z
H
C N Z +H2O
Reactions of Aldehydes and KetonesOxidation:Aldehydes readily get oxidized to give CarboxyacidsR C
H
O[O]
Na2Cr2O7 + H2SO4
R COOH
Slide 28R C
H
O[O]
Na2Cr2O7 + H2SO4
R COOH
Reactions of Aldehydes and KetonesWith Tollen’s reagent
R C
H
O + 2[Ag(NH3)2]+ + 3 OH
- RCOO + 2 Ag + 2H2O + 4NH3
Silver Mirror
Slide 29
R C
H
O + 2[Ag(NH3)2]+ + 3 OH
- RCOO + 2 Ag + 2H2O + 4NH3
Silver Mirror
Reactions of Aldehydes and KetonesWith Fehling solution
Slide 30R C
H
O + 2Cu2+
+5OH RCOO + Cu2O +3H2O
Red ppt
Reactions of Aldehydes and KetonesOxidation of Ketones:In presence of strong oxidising agents at high temperatureketones get oxidized . Their oxidation involves C-C bondcleavage. A mixture of Carboxylic acids having lesser number ofcarbon atoms formed.
Slide 31
Oxidation of Ketones:In presence of strong oxidising agents at high temperatureketones get oxidized . Their oxidation involves C-C bondcleavage. A mixture of Carboxylic acids having lesser number ofcarbon atoms formed.CH3 C
O
CH3 CH3COOH + CO2 + H2OEx:alkaline
KMnO44[O]
Reactions of Aldehydes and KetonesReduction: Aldehydes and Ketones are reduced to primary andsecondary alcohol by using LiAlH4 /NaBH4
R C
H
OLiAlH4
THFR CH2 OH
Primary Alcohol
LiAlH4
THFR C
H
OH
R
Secondary Alcohol
R C
O
R Slide 32
R C
H
OLiAlH4
THFR CH2 OH
Primary Alcohol
LiAlH4
THFR C
H
OH
R
Secondary Alcohol
R C
O
R
Reactions of Aldehydes and KetonesReduction to Hydrocarbons (Clemmensen reduction)R C
H
O R CH3 + H2O
+ H2OR C
O
R R CH2 R
Zn - Hg
Concentrated HCl
Zn - Hg
Concentrated HCl Slide 33
R C
H
O R CH3 + H2O
+ H2OR C
O
R R CH2 R
Zn - Hg
Concentrated HCl
Zn - Hg
Concentrated HCl
Reactions of Aldehydes and KetonesWolf-Kishner reductionR C
H
O
R C
O
R
R CH3 + H2O
R CH2 R + H2O
KOH/NaOH
NH2 NH2
KOH
NH2 NH2
Slide 34
R C
H
O
R C
O
R
R CH3 + H2O
R CH2 R + H2O
KOH/NaOH
NH2 NH2
KOH
NH2 NH2
Reactions of Aldehydes and KetonesReactive α- HydrogenThe α-Hydrogen in aldehydes and ketones is acidic in nature. Itis due to the strong electron withdrawing group.C O
Slide 35
Reactive α- HydrogenThe α-Hydrogen in aldehydes and ketones is acidic in nature. Itis due to the strong electron withdrawing group.C O
Reactions of Aldehydes and KetonesAldol condensation
CH3 C
H
O CH3 C
H
Odil NaOH
CH3 C
H
OH
CH2 C
H
O
CH3 CH CH C
H
O
But - 2 - enalaldol
3 - Hydroxy butanal
acetaldehyde acetaldehyde
CH3 C
O
CH3 CH3 C
O
CH3
Ba(OH)2CH3 C
OH
CH3
CH2 C
O
CH3CH3 C CH C
O
CH3
CH34 - Methyl pent - 3en - 2 one
Ketal(4 - Hydroxy, 4 - Methyl Pentan - 2 one)
Slide 36
CH3 C
H
O CH3 C
H
Odil NaOH
CH3 C
H
OH
CH2 C
H
O
CH3 CH CH C
H
O
But - 2 - enalaldol
3 - Hydroxy butanal
acetaldehyde acetaldehyde
CH3 C
O
CH3 CH3 C
O
CH3
Ba(OH)2CH3 C
OH
CH3
CH2 C
O
CH3CH3 C CH C
O
CH3
CH34 - Methyl pent - 3en - 2 one
Ketal(4 - Hydroxy, 4 - Methyl Pentan - 2 one)
Reactions of Aldehydes and KetonesCross aldol condensationBenzaldehyde + Acetophenone OH-/ Δ 1,3-Diphenylprop-2-enone
Slide 37C
O
H CH3 C
O
C
OH
H
CH2 C
O
-H2O
CH CH C
O
1.3 . diphenyl Propzentone
OH
Dil NaOH
Reactions of Aldehydes and KetonesElectrophilic Substiution:Aromatic aldehydes and Ketones undergo electrophillicsubstitution to give meta- substituted product
C
H
OC
H
O
NO2Metanitro benzaldehyde
Concentrated HNO3
Concentrated H2SO4
Slide 38C
H
OC
H
O
NO2Metanitro benzaldehyde
Concentrated HNO3
Concentrated H2SO4
Reactions of Aldehydes and KetonesCannizzaro’s reaction(Reactions + Aldehydes which have no α – Hydrogen
2 H C O
HKOH
50%HCOOK + CH3OH
Potassiumformate
Methanol
2C
H
O KOH50%
COOK CH2 OH
PotassiumBenzoate
BenzylacloholSlide 39
2 H C O
HKOH
50%HCOOK + CH3OH
Potassiumformate
Methanol
2C
H
O KOH50%
COOK CH2 OH
PotassiumBenzoate
Benzylaclohol
Reactions of Aldehydes and KetonesUses(i) :FormaldehydeIn the manufacture of latex rubber.Preparation of Formalin(40% solution for preserving biologicalspecimen), Trioxane , Bakelite(Thermosetting polymer) &Urotropine(urinary antiseptic)Uses(ii) : AcetaldehydeIn the preparation of acetic acid , ethyl acetate & vinyl acetate.Paraldehyde(hypnotic) and metaldehyde(solid fuel) Slide 40
Uses(i) :FormaldehydeIn the manufacture of latex rubber.Preparation of Formalin(40% solution for preserving biologicalspecimen), Trioxane , Bakelite(Thermosetting polymer) &Urotropine(urinary antiseptic)Uses(ii) : AcetaldehydeIn the preparation of acetic acid , ethyl acetate & vinyl acetate.Paraldehyde(hypnotic) and metaldehyde(solid fuel)
Reactions of Aldehydes and KetonesUses(iii) : BenzaldehydeUsed in perfumery, dye industriesUsed as flavoring agentUsed in the preparation of Cinnamic acid, Malachite greenUses (iv) : AcetoneUsed as industrial solventUsed in the preparation chloretone(hypnotic), Mesityl oxide,Phorone, Mesityline, chloroform and iodoform Slide 41
Uses(iii) : BenzaldehydeUsed in perfumery, dye industriesUsed as flavoring agentUsed in the preparation of Cinnamic acid, Malachite greenUses (iv) : AcetoneUsed as industrial solventUsed in the preparation chloretone(hypnotic), Mesityl oxide,Phorone, Mesityline, chloroform and iodoform
Reactions of Aldehydes and KetonesUses (v) :AcetophenoneUsed in the preparation of Tear gas phenacyl chlorideUsed in the preparation of a hypnotic ‘Dypnone’
Slide 42
Uses (v) :AcetophenoneUsed in the preparation of Tear gas phenacyl chlorideUsed in the preparation of a hypnotic ‘Dypnone’
1. Which is the most suitable oxidising agent used to convertprimary alcohol into an aldehyde?(a) Acidified K2Cr2O7 (b) Acidified KMnO4(c) Alkaline KMnO4 (d)
Slide 44
1. Which is the most suitable oxidising agent used to convertprimary alcohol into an aldehyde?(a) Acidified K2Cr2O7 (b) Acidified KMnO4(c) Alkaline KMnO4 (d)2. When PCC is used as an oxidising agent, which is the solventused?(a) T.H.F (b) Diethyl ether(c) (d) Carbon disulphide
PCC
Dichloromethane
3. Which is the product obtained 2–Pentene undergoesozonolysis followed by treating with Zn + H2O?(a) Acetone (b) Acetaldehyde(c) Propionaldehyde (d) Acetaldehyde and propionaldehyde
Slide 454. What is product formed, when vapours of acetic acid arepassed over heated MnO at 573K?(a) Formaldehyde (b) Acetaldehyde(c) (d) Acetic anhydrideAcetone
5. What is the product formed when propyne is treated withdilute H2SO4 in presence of HgSO4 catalyst?(a) Propene (b) Propanal(c) Propanol (d)Propanone
Slide 46
5. What is the product formed when propyne is treated withdilute H2SO4 in presence of HgSO4 catalyst?(a) Propene (b) Propanal(c) Propanol (d)6. Phenyl cyanide treated with SnCl2+ con. HCl and the productformed treated with dilute acid gives(a) Phenol (b) Benzoic acid(c) (d) Benzyl alcohol
Propanone
Benzaldehyde
In this, reactant A is(a) CO2 (c) (d) CH3OH
7. CH3 MgI + ADry Ether
BH2O
H+CH3CHO
Slide 47
In this, reactant A is(a) CO2 (c) (d) CH3OH(b) CH3 C
OCH3
7. CH3 MgI + ADry Ether
BH2O
H+CH3CHO
HCN
8. In the reactionwhich is the electrophile?(a) (b) (c) (d)
CHO
+CO + HCl +HClAnhydrous
AlCl3
Slide 48
8. In the reactionwhich is the electrophile?(a) (b) (c) (d)CO CHO Cl CHO
CHO
+CO + HCl +HClAnhydrous
AlCl3
9. A dihaloalkane on alkaline hydrolysis produces a ketone withformula C3H6O. The compound is(a) 1,2-Dichloropropane (b) 1,1-Dichloropropane(c) (d) 1,3-Dichloropropane2,2-Dichloropropane
Slide 49
9. A dihaloalkane on alkaline hydrolysis produces a ketone withformula C3H6O. The compound is(a) 1,2-Dichloropropane (b) 1,1-Dichloropropane(c) (d) 1,3-Dichloropropane10. Which one of the following is present in the blood ofdiabetic patient?(a) Methanol (b) Ethanoic acid(c) (d) Propanal
2,2-Dichloropropane
Propanone
11. 3-Pentanone and 2-Pentanone are(a) (b) Chain Isomers(c) Functional isomers (d) Optical isomersMetamers
Slide 50
11. 3-Pentanone and 2-Pentanone are(a) (b) Chain Isomers(c) Functional isomers (d) Optical isomers12. In aldol condensation the intermediate formed is(a) Carbonium ion (b) Nitrene(c) Carbene (d) Enolate ion
13.The product formed when Benzaldehyde is treated withacetaldehyde in presence of dilute NaOH is(a) Benzyl alcohol (b) Ethanol(c) Benzoic acid (d)Slide 51
13.The product formed when Benzaldehyde is treated withacetaldehyde in presence of dilute NaOH is(a) Benzyl alcohol (b) Ethanol(c) Benzoic acid (d) 3–Phenyl prop-2-enal
14.Identify A in the above reaction.(a) Acetone (b) Acetaldehyde(c) Formaldehyde (d)
CH3 MgI + A B PropaneDry
Ether
NH2 - NH2
KOH
Slide 52
14.Identify A in the above reaction.(a) Acetone (b) Acetaldehyde(c) Formaldehyde (d)
CH3 MgI + A B PropaneDry
Ether
NH2 - NH2
KOH
Ethane nitrile
15. Haloform reaction is given by the compounds having(a) CH2 – OH group (b) – COOH Group(c) – COOCH3 group (d)C
O
CH3
Slide 53
15. Haloform reaction is given by the compounds having(a) CH2 – OH group (b) – COOH Group(c) – COOCH3 group (d)C
O
CH3
16. Acetaldehyde and Benzaldehyde differ in reaction with(a) Tollen’s Reagent (b) HCN(c) NaHSO3 (d)Dilute NaOH
17. Dypnone, a hypnotic is obtained from(a) Acetone (b) Acetaldehyde(c) (d) BenzaldehydeAcetophenone
Slide 54
17. Dypnone, a hypnotic is obtained from(a) Acetone (b) Acetaldehyde(c) (d) Benzaldehyde18. Phenacyl Chloride prepared from acetophenone is used as(a) Polymer (b) Antioxidant(c) (d) Antiseptic
Acetophenone
Lachrymater
19.Which one of the following statements is wrong?(a)(b) Aldehydes and ketones are polar compounds.(c) Aldehydes are more reactive than ketones.(d) Aldehydes and ketones are reduced to alcohols.
Aldehydes and ketones are good reducing agents.
Slide 55
19.Which one of the following statements is wrong?(a)(b) Aldehydes and ketones are polar compounds.(c) Aldehydes are more reactive than ketones.(d) Aldehydes and ketones are reduced to alcohols.
Aldehydes and ketones are good reducing agents.
20.(a) (b) (c) RCOOH (d)R C C H
H2O 70 oC
H2SO4 +HgSO4
A A is
R C O
H R C CH3
O
Slide 56
20.(a) (b) (c) RCOOH (d)
21. Both formaldehyde and acetaldehyde give similar reactionswith all the reagents except(a) Schiff reagent (b) Tollen’s reagent(c) (d) Fehling solution
R C O
H R C CH3
OR CH2 OH
Ammonia
22. In the Cannizzaro’s reaction, the slowest step is(a) Attack of OH on Carboxyl group(b)(c) Removal of H+ from COOH(d) Attack of H+ on Carboxyl groupThe transfer of Hydride ion to the Carboxyl group
Slide 57
22. In the Cannizzaro’s reaction, the slowest step is(a) Attack of OH on Carboxyl group(b)(c) Removal of H+ from COOH(d) Attack of H+ on Carboxyl group23. C2H5CHO and can be distinguished using(a) Phenyl hydrazine (b) Hydroxyl amine(c) Sodium bisulphate (d)CH3 C
O
CH3
Fehling solution
24. Acetophenone is converted into Ethyl benzene by using(a) NaBH4 (b) LiAlH4(c) Sodium + Alcohol (d)Zn–Hg + Con. HCl
Slide 58
25. In Rosenmund reduction the role of BaSO4 is(a) Catalyst(b) Prometer(c) To absorb the heat evolved(d) To decrease the activity of catalyst palladium
26.Here B is(a) CH3CH2OH (b) CH3CN(c) CH3CH=N – OH (d)
CH3 C O
H
+ NH2 OH
LiAlH4A B
Slide 59
26.Here B is(a) CH3CH2OH (b) CH3CN(c) CH3CH=N – OH (d)
CH3 C O
H
+ NH2 OH
LiAlH4A B
CH3 – CH2 – NH2
27. Crossed aldol condensation is not given by(a) Acetaldehyde and Acetone(b) Acetaldehyde and Benzaldehyde(c) Propionaldehyde and Acetaldehyde(d) Slide 60
27. Crossed aldol condensation is not given by(a) Acetaldehyde and Acetone(b) Acetaldehyde and Benzaldehyde(c) Propionaldehyde and Acetaldehyde(d) Benzaldehyde and Formaldehyde
28.Here C is(a) (b)(c) (d)
CH3 C CH3
O
+ CH3 MgIEther H2O
H+A B
Copper
300 oCC
Slide 61
28.Here C is(a) (b)(c) (d)CH3 CH CH2 CH3 C
CH3
CH2
CH3 CH2 CH2 OH CH3 COOH
29. A compound gave a positive Tollen’s test. It also answeredhaloform test. The compound was(a) (b) Acetone(c) Acetophenone (d) PropanalEthanal
Slide 62
29. A compound gave a positive Tollen’s test. It also answeredhaloform test. The compound was(a) (b) Acetone(c) Acetophenone (d) Propanal30. On reduction with LiAIH4, which of the following gives anoptically active compound?(a) Propanal (b) Propanone(c) Butanol (d) Butanone
31. Which of the following has highest boiling point ?(a) Propanone (b) 2-Pentanone(c) Butanone (d) 2-Hexanone
Slide 63
31. Which of the following has highest boiling point ?(a) Propanone (b) 2-Pentanone(c) Butanone (d)32. Benzaldehyde does not react with(a) Tollen’s reagent (b)(c) 2,4-DNP solution (d) NaHSO3
2-HexanoneFehling solution
33. Which one of the following gives violet colour with neutralFerric Chloride solution?(a) Acetaldehyde (b) Benzaldehyde(c) (d) FormaldehydeSalicylaldehyde
Slide 64
33. Which one of the following gives violet colour with neutralFerric Chloride solution?(a) Acetaldehyde (b) Benzaldehyde(c) (d) Formaldehyde34. Which one of the following is used to convert Benzaldehydeinto Toluene?(a) LiAlH4 (b) NaBH4(c) Sodium and alcohol (d)
Salicylaldehyde
Zn-Hg + Con. HCl
35. A carbonyl compound reacts with hydrogen cyanide to formcyanohydrin which on hydrolysis forms a racemic mixture of α-hydroxy acids. The carbonyl compound is(a) Diethyl ketone (b) Dimethyl ketone(c) Formaldehyde (d)Slide 65
35. A carbonyl compound reacts with hydrogen cyanide to formcyanohydrin which on hydrolysis forms a racemic mixture of α-hydroxy acids. The carbonyl compound is(a) Diethyl ketone (b) Dimethyl ketone(c) Formaldehyde (d) Acetaldehyde
36. Iodoform test is not given by(a) Pentan-2-one (b) Ethanol(c) (d) EthanalPentan-3-one
Slide 66
36. Iodoform test is not given by(a) Pentan-2-one (b) Ethanol(c) (d) Ethanal37. CH3CHO and C6H5CH2CHO can be distinguished by(a) Benedict’s test (b) Tollen’s reagent test(c) (d) Fehling’s reagent test
Pentan-3-oneIodoform test
38. An aromatic compound X with molecular formula C9H10O gives2,4-DNP test, Tollen;s test, undergoes Cannizaro reaction and onvigarous oxidation gives 1,2-benzene dicarboxylic acid. X is(a) 2-Methylacetophenone (b) 3-Ethylbenzaldehyde(c) (d) 3-MethylacetophenoneSlide 67
38. An aromatic compound X with molecular formula C9H10O gives2,4-DNP test, Tollen;s test, undergoes Cannizaro reaction and onvigarous oxidation gives 1,2-benzene dicarboxylic acid. X is(a) 2-Methylacetophenone (b) 3-Ethylbenzaldehyde(c) (d) 3-Methylacetophenone2-Ethylbenzaldehyde
39. Aldol condensation between which of the following twocompounds followed by dehydration gives methyl vinyl ketone?(a)(b) Formaldehyde and acetaldehyde(c) Two molecules of acetaldehyde(d) Two molecules of acetoneFormaldehyde and acetone
Slide 68
39. Aldol condensation between which of the following twocompounds followed by dehydration gives methyl vinyl ketone?(a)(b) Formaldehyde and acetaldehyde(c) Two molecules of acetaldehyde(d) Two molecules of acetone
40. Which of the following reactions will not result in the formationof carbon-carbon bonds?(a) Friedel-Craft acylation(b) Reimer- Tiemann reaction(c) Wurtz reaction(d) Slide 69
40. Which of the following reactions will not result in the formationof carbon-carbon bonds?(a) Friedel-Craft acylation(b) Reimer- Tiemann reaction(c) Wurtz reaction(d) Cannizzaro reaction
41. Trichloroacetataldehyde is subjected to Cannizzaro’s reactionby using NaOH. The mixture of the products contains sodiumtrichloroacetate and another compound. The other compound is(a) Trichloromethanol(b) 2,2,2-Trichloropropanol(c) Chloroform(d) Slide 70
41. Trichloroacetataldehyde is subjected to Cannizzaro’s reactionby using NaOH. The mixture of the products contains sodiumtrichloroacetate and another compound. The other compound is(a) Trichloromethanol(b) 2,2,2-Trichloropropanol(c) Chloroform(d) 2,2,2-Trichloroethanol
42. Consider the reaction:RCHO+NH2NH2 → RCH=N-NH2What sort of reaction is this?(a) Electrophilic addition-elimination reaction(b) Free radical addition-elimination reaction(c) Electrophilic substitution-elimination reaction(d) Slide 71
42. Consider the reaction:RCHO+NH2NH2 → RCH=N-NH2What sort of reaction is this?(a) Electrophilic addition-elimination reaction(b) Free radical addition-elimination reaction(c) Electrophilic substitution-elimination reaction(d) Nucleophilic addition-elimination reaction
43. Which of the following ketones cannot be prepared bypyrolysis of a suitable calcium salt of a fatty acid?(a) Benzophenone (b) Pentan-3-one(c) (d) Propanone
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43. Which of the following ketones cannot be prepared bypyrolysis of a suitable calcium salt of a fatty acid?(a) Benzophenone (b) Pentan-3-one(c) (d) Propanone44. Cyanohydrin of which of the following gives lactic acid onhydrolysis?(a) CH3COCH3 (b) HCHO(c) C6H5CH2CHO (d)
Butanone
CH3CHO
45. Which of the following reagents can help in separating amixture of acetone and isopropyl alcohol?(a) NaOH (b) NaCl(c) (d) NaHSO4
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45. Which of the following reagents can help in separating amixture of acetone and isopropyl alcohol?(a) NaOH (b) NaCl(c) (d) NaHSO4NaHSO3
46. Arrange the following compounds in increasing order of theirreactivity in nucleophilic addition reactions; Ethanal(I),Propanal(II), Propanone(III) and Butanone(IV).(a) III<II<I<IV (b) II<I<III<IV(c) (d) I<II<III<IV
Slide 74
46. Arrange the following compounds in increasing order of theirreactivity in nucleophilic addition reactions; Ethanal(I),Propanal(II), Propanone(III) and Butanone(IV).(a) III<II<I<IV (b) II<I<III<IV(c) (d) I<II<III<IVIV<III<II<I
47. Which of the following compounds does not react with sodiumbisulphate?(a)Benzaldehyde (b)(c)Acetone (d)AcetaldehydeSlide 75
47. Which of the following compounds does not react with sodiumbisulphate?(a)Benzaldehyde (b)(c)Acetone (d)AcetaldehydeAcetophenone
48. A compound A has molecular formula C2Cl3OH. It reducesFehling’s solution and on oxidation gives a monocarboxylicacid B. A is obtained by the action of Cl2 on ethyl alcohol. A is(a) (b) Chloroform(c) Chloromethane (d) Chloroacetic acidSlide 76
48. A compound A has molecular formula C2Cl3OH. It reducesFehling’s solution and on oxidation gives a monocarboxylicacid B. A is obtained by the action of Cl2 on ethyl alcohol. A is(a) (b) Chloroform(c) Chloromethane (d) Chloroacetic acid49. Acetone on distillation with conc. H2SO4 forms(a) Phorone (b) Acrolein(c) (d) Mesityl oxide
Chloral
Mesitylene
50. Compound A C5H10O forms a phenylhydrozone and gives negativeTollen’s & iodoform test. On reduction it gives n-pentane. A is(a) Pentanal (b) Pentan-2-one(c) (d) Amyl alcohol
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50. Compound A C5H10O forms a phenylhydrozone and gives negativeTollen’s & iodoform test. On reduction it gives n-pentane. A is(a) Pentanal (b) Pentan-2-one(c) (d) Amyl alcohol51. With which of the following reagents, carbonyl compound showsaddition cum elemination reaction?(a) Carbonium ion (b)(c) HCN (d) NaHSO3
Pentan-3-oneBrady’s reagent
52. Which one of the following is crotonaldehyde?(a) CH2=CH-CHO (b) C6H5-CH=CH-CHO(c) (d) C6H5(OH)CHOCH3-CH=CH-CHO
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52. Which one of the following is crotonaldehyde?(a) CH2=CH-CHO (b) C6H5-CH=CH-CHO(c) (d) C6H5(OH)CHO53. Which of the following will give negative test with Brady’reagent?(a)CH3CHO (b)(c) CH3-CO-CH3 (d) C6H5CHOCH3-O-CH3
54. The reaction of chloroform with acetone gives(a) Mesityline (b) Ethylidene chloride(c) (d) ChloralChloretone
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54. The reaction of chloroform with acetone gives(a) Mesityline (b) Ethylidene chloride(c) (d) Chloral55. Hexamethylene tetramine is used as(a) Analgesic (b) Antipyrtic(c) Hypnotic (d) Urinary antiseptic
56. Reaction involving formation of trioxane from methanal iscalled(a) Aldol condensation(b) Condensation polymerization(c)(d) Cannizzaro’s reactionSlide 80
56. Reaction involving formation of trioxane from methanal iscalled(a) Aldol condensation(b) Condensation polymerization(c)(d) Cannizzaro’s reactionAddition polymerzation
57. What is Stephan’s reaction?(a) An alkyl isocyanide is reduced with Na/alcohol.(b) An alkyl cyanide is reduced with LiAlH4.(c) An alkanoyl chloride is reduced with Pd/BaSO4.(d)Slide 81
A57. What is Stephan’s reaction?(a) An alkyl isocyanide is reduced with Na/alcohol.(b) An alkyl cyanide is reduced with LiAlH4.(c) An alkanoyl chloride is reduced with Pd/BaSO4.(d) An alkyl cyanide is reduced with SnCl2 and HCl.
58. Schiff ’s reagent is:(a) Magenta solution decolourised with chlorine.(b) Ammonical cobalt chloride solution.(c)(d) Cannizzaro’s reactionSlide 82
58. Schiff ’s reagent is:(a) Magenta solution decolourised with chlorine.(b) Ammonical cobalt chloride solution.(c)(d) Cannizzaro’s reactionRosaniline hydrochloride decolourised with H2SO3.
59. Which of the following reactions is a condensation reaction?(a) HCHO → Paraformaldehyde(b)(c) CH3CHO → Paraldehyde(d) H2C=CH2 → PolyethyleneCH3COCH3 → Mesityl oxide
Slide 83
59. Which of the following reactions is a condensation reaction?(a) HCHO → Paraformaldehyde(b)(c) CH3CHO → Paraldehyde(d) H2C=CH2 → Polyethylene
60. In the following sequence of reaction, end product isCaC2 H2O A Hg2+/H2SO4 B [O] C Ca(OH)2/ heat D(a) Acetaldehyde (b) Formaldehyde(c) Acetic acid (d)
Slide 84
60. In the following sequence of reaction, end product isCaC2 H2O A Hg2+/H2SO4 B [O] C Ca(OH)2/ heat D(a) Acetaldehyde (b) Formaldehyde(c) Acetic acid (d) Acetone
Slide 85Thank You.