C - Sol - Ch-24 - Aldehydes, Ketones and Carboxylic Acids

Chapter 24
Aldehydes, Ketones and Carboxylic Acids

1. Answer (A)
O3 CHO intramolecular
CHO
Zn, H2O CHO aldol condensation
E F
2. Answer (C)
O O O O
 I2 + NaOH
–CO2 C  C 
iodoform reaction
Ph  OH Ph CH3 Ph ONa + CHI3
-keto acid E G
3. Answer (C)
O H O
–
C C

O –H O
H H
O O
Most acidic Stabilized by strong
intramolecular hydrogen
bonding
4. Answer (B)
H
– H :O – CH2 – R
:
CH2
O O O O R
H

–H
CH2 – R
O O
An acetal
5. Answer (C)
CH2OH
|
OH + HCHO/OH
CH3 — CHO + H — CHO 
Aldol
 HOCH2 — CH2 — CHO 
Aldol
HOCH2 — CH — CHO
CH2OH CH2OH
| |
+ HCHO/OH + HCHO/OH

Aldol
HOCH2 — C — CHO 
Cannizzaro HOCH2 — C — CH2OH
| |
CH2OH CH2OH
 Number of aldol reactions = 3
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CHEMISTRY ARCHIVE - JEE (Advanced) (Solutions)
6. Answer (B)
COOH
O
 -keto acid undergoes easy decarboxylation just by heating through the formation of six membered
transition state.
7. Answer (A)
O OH CN COOH
CN 95% H2SO4
CH3 – CH2 – C – CH3 CH3 – CH2 – C – CH3 
CH3 – CH = C – CH 3
8. Answer (D)
Carbolic acid (Phenol) is weaker acid than carbonic acid and hence does not liberate CO2 on treatment with
aq. NaHCO3 solution. Benzoic acid, benzenesulphonic acid and salicylic are more acidic than carbonic acid
and hence will liberate CO2 with aq. NaHCO3 solution.
9. Answer (D)
O O– CH3
Cl Cl
CH3
CH3
O
CH3 – MgI
10. Answer (A)
COOH O
– O
H C H
HO OH
O O
(I)
(stabilizes by H-bonding)
COOH O O– H
OH O
(II) (stabilizes by H-bonding)
COOH COO–
OH OH
(III) (stabilizes by –I effect)
COOH COO–
OH OH
(IV) (destabilizes of +m effect)
 Acidity order is I > II > III > IV.

ARCHIVE - JEE (Advanced) (Solutions) CHEMISTRY
11. Answer (A)
O O
C C
H – CH = O, NaOH, 
(crossed aldol condensation)
CH2
OH
OH O O
H H
C=O C=O
H H
OH , 
–
H+
HO
12. Answer (B)
I. HC  C  COOH
sp
II. H2C  CH
2
 COOH
sp
III. MeO COOH

(EDG) 2
sp
IV. H3 C  CH2  COOH

sp3
+I effect decreases the acidic character of carboxylic acid and –I effect increases the acidic character.
Since the electronegativity order of 'C' attached to carboxylic acid is sp > sp2 > sp3, hence the order is
I > II > III > IV.
II is more acidic than III since the electron donating group is attached to benzene ring.
13. Answer (C, D)
X (CH2)4 X
In C and D diamine is obtained which will give polyamide with dicarboxylic acid.
14. Answer (B, D)
C6H5COOH + NaOH  C6H5COONa + H2O
C6H5COOH + NaHCO3  C6H5COONa + CO2 + H2O
C6H5CH2 – OH + NaOH  No reaction
C6H5CH2OH + NaHCO3  No reaction
C6H5CH2COOH + NaOH  C6H5CH2 – COONa + H2O
C6H5CH2COOH + NaHCO3  C6H5CH2COONa + CO2 + H2O
C6H5CH2OH + NaOH  No reaction
C6H5CH2OH + NaHCO3  No reaction

15. Answer (A, C, D)
OCOCH 3
O
CH2OH CH2
O OH Excess (CHCO) OCOCH 3
LiAlH 4 3 2O
H3C H3C H3C

T Optically W
inactive (Molecular formula C10H18O4 )
(U)
COOH
+
CrO3/H
COOH
H3C
V
Hence answer is (A, C, D).

16. Answer (A, B, C, D)
AlCl3
(i) Cl AlCl4 (P)
(AROMATIC)
Na
NaH
(ii) (Q) + H2
(AROMATIC)
(NH4)2CO3
R
(iii) 100–115ºC
O O

(NH4)2CO3 2NH3 + CO2 + H2O
 IMPE
+ NH3
O O O O NH2 O NH2 OH
H
H H H H
N N N
 IMPE
–2H2O
HO OH O OH
(R) AROMATIC
HCl
(iv) O OH Cl (S)
(AROMATIC)

17. Answer (C)

O
Reaction I : C Br2 (1.0 mol)

CHBr3 + CH3COONa
CH3 CH3 aqueous NaOH
(1.0 mol)
O O
Br2 (1.0 mol)
Reaction II : C CH3COOH
C
CH3 CH3 CH3 CH2Br
(1.0 mol)
18. Answer (A)
CH3 CH3
CH3 O OH
O H O O O +
O
KOH, H2 O H
CH3
O
O O

+
(Minor) (Major)
19. Answer (A, B, C)
All aldehydes gives Tollen's test as shown below
O
R – CH = O + [Ag(NH3)2 ] R – C – O– + Ag+ NH+4
+
(Silver mirror)
-hydroxy ketones are oxidised to 1, 2 diketones and Ag+ is reduced to Ag.
OH O O O
+
[Ag(NH3)2]
Ph – CH – C – Ph Ph – C – C – Ph + Ag+ NH+4
20. Answer (B, C)
O O
(i) O3/CH2Cl2
CH3 CH3 C–H+H–C–H
(ii) Zn/H2O
Undergoes
Cannizzaro's
reaction
CH2 O O
O3/CH2 Cl2
C C + H–C–H
Zn/H2O
CH3 CH3
Undergoes
Haloform reaction
O O
O3/CH2 Cl2
CH3 C – H + CH3 – C – H
Zn/H2O
CH3 CH3 Undergoes

Cannizzaro's reaction
CH3
CH3 O CH3 CH3
O3/CH2Cl2
C +
Zn/H2O
CH3 O
CH3
CH3 Undergoes
Haloform reaction

21. Answer (A, B, D)

H
H
C
H O Me Me
Me C C Me Conc.H2SO4
+ 3H2O
(A) O C H 
H H H
H Me
C O
H C
Me
Me
|
C H Me Me
H C
C Heated iron tube
(B) 873K
C C
Me C Me
Me
|
H
O O
|| O Na
C—Me C
| |
(C)
Br2/NaOH
(Haloform reaction)
Me
Me—C C C C—O Na
|| || Na O || ||
O O O O
+
3H3O
COOH
Soda lime

(decarboxylation)
COOH COOH
CHO CH3
Zn/Hg,HCl
(D) (Clemmensen reduction)
OHC CHO CH3 CH3

22. Answer (B, D)

O
C C – CH2 – CHO C – CH2 – CH2 – CHO
HgSO4, H2SO4 (dil.)
OMe OMe AgNO3, NH4OH
O O
–
CH2 – CH2 – CH2 – COOH C – CH2 – CH2 – C – O
Zn-Hg
(Q)
HCl
OMe OMe
SOCl2 , Py
O
CH2 – CH2 – CH2 – C – Cl
AlCl3 O Zn-Hg
(S)
HCl
OMe OMe OMe

(R)
23. Answer (B, D)
O
O
CH3 CH3
H3C H3C CH3 CH3 H3C CH 3
O (i) Zn - Hg/HCl
H 3C CH3
AlCl 3 (ii) H 3PO 4
(P)
C=O
HOOC
(Q)
CH3 H C CH3 CH 3 H C CH3

H3C 3
(i) CH3 MgBr
H 3C 3
H 3C +
H3C
(ii) H 3O
H 3C
O (iii) H 2SO 4/D
(R) (S)
24. Answer (A, B)
CH 3 CH3
N2Cl CN
CuCN
(A)
273 K
DIBAL – H

then HO
3
O
N2H4 C H
KOH, 

CH 3 O O
Br (1) Mg/THF
C OH C Cl
SOCl2
(B) (2) CO2
+
(3) H /H2 O
H2 /Pd-BaSO4
Zn-Hg
C H
HCl
CH 3 CH 3 CH 3
(i) BH3 H 2O2/OH
–
(C)
BH 2 OH
PBr3
Zn
dil HCl
Br
O
C H
(D) O3 O N2H4
Zn/H2O C H KOH, 
25. Answer (A, C)
O
O
O O
Zn/Hg
AlCl3 HO HCl OH
O O
(P) (Q)
SOCl2
Zn/Hg AlCl3
HCl Cl
O O
[Hydrocarbon] (S) (R)
Compound (S) can not decolorizes bromine water.
R2Cd
Cl R
O O
R2Cd is a less reactive nucleophile so reaction stops at carbonyl group.
26. Answer (C)
27. Answer (C)

28. Answer (B)

29. Answer (D)
30. Answer (A)
31. Answer (C)
Solution of Q. Nos. 29 to 31
O
(1) NaBH4
H3C CH2 C C CH2 C H CH3CH2 C C CH2 CH2Br
(2) PBr3
(I)
(1) Mg/Ether
(2) CO2
+
(3) H3O
Me Cl SOCl2
CH3 CH2 C C CH2 CH2COOH
O (J)
(K)
H2/Pd, BaSO4 , quinoline

(Lindlar’s calatyst)
CHO
(cis product) (L)
32. Answer (B)

33. Answer (A)
34. Answer (D)
O OH
Ph – C – CH3 + PhCH2MgBr Ph – C – CH2 – Ph
CH3 H
Conc. H2SO4 dehydration
Ph – C = CHPh Ph CH3
or
CH3 H Ph
I
Ozonolysis
O
Ph – C = O + Ph – C – H
CH3 J
K Cannizzaro's
KOH reaction
Aldol followed
KOH
by dehydration
PhCH2OH + PhCOOK
O
H3C L
Ph Ph
H
M

35. Answer (B)

36. Answer (A)
37. Answer (B)
Me Me Me
(i) MeMgBr H2SO4 (i) O3
(ii) H3O
+ OH (ii) Zn-H2O
O Me Me Me Me Me
P Q
– Me
(i) OH/H2O O
O
(ii) H , 
+
C
O Me
Me Me Me Me
S R
38. Answer (B)
39. Answer (A)
40. Answer (D)
Solution of Q.Nos. 38 to 40
CH3 O
H3C
1. K2CO3 C
C H
2. H H C H
H3C C H3C
H C
(Q) CH2
(P) O 3. H+
O OH
(R)
HCN
OH
H3C CN
CH O
C C H3C
H3C CH
Hydrolysis
C OH
H2C HO H3C
O H CH2
 OH
(S)
OH
H3C
C O
H3C
H2C O
41. Answer (C)

42. Answer (A)
Solution of Q. Nos. 41 and 42
CHO CH = CH–COOH
(CH3CO)2 O (i) H2 , Pd/C

CH3 COONa (ii) SOCl2
(iii) Anhyd. AlCl3
O
43. Answer (B)
H COOH COOH
dil. alk. KMnO4 H OH
C
H OH
C
COOH
H COOH
(S)
(P)
H COOH
COOH COOH
C dil. alk. KMnO4 H OH HO H
C HO H + H OH
HOOC H COOH COOH
(Q) (T) (U)
44. Answer (A)
O
H COOH
C H2/Ni
O

C
HOOC H
(Q) O
(V)
O O
Zn(Hg)
O+ AlCl3 H3PO3
anhydrous HCl
HO HO
O O O O
(V) (W)
45. Answer (A)
O O
NH2
KMnO4/H +
C OH NH3 C NH2 Br2/NaOH
 C OH  C NH2 (Hoffman bromamide)
NH2
O O
(P) (Q) (R)

46. Answer (B)

C
Br – C
C=O
O
O O O
CH2
C – NH2 C C C
 CH3
–NH3
N–H N–C
C=O
C – NH2 C C
(Q) (S)
O (Phthalimide) O O O
CH2
+
H3O
CH3
O
O C – OH
C – C – C – OH+
NH2 C – OH
(alanine)
(T) O
47. Answer (C)
48. Answer (C)
Solution of Q. Nos. 47 and 48
– +
O OMgBr
C(CH3)3 C – OEt CH3MgBr (excess)/(C2H5)2O C(CH3)3 CH3–C–CH3
(P)
H2O
H H
O O–H
C(CH3)3 C(CH3)2 H2SO4/ C(CH3)3 CH3–C–CH3
0°C
(Q)
–H2O (dehydration)
O CH3
CH3 CH3
CH3 CH3–C–Cl/AlCl3 C(CH3)3
C(CH3)3 C(CH3)2 C(CH3)3 (Acylation)
(alkylation)
(R) COCH3
(S)
49. Answer (C)
CHO O—H
COOH
Br Moist
CO/HCl Ac2O Br2/Na 2 CO3
AlCl3 AcONa KOH
COOH
(anhy.) D
CuCl (X) (473 K) (Y)

50. Answer (A)
O
CO/HCl – C– H AC2O/NaOAC – CH = CH – COOH
AlCl3/CuCl
(X)
H2/Pd–C
– CH2 – CH 2 – COOH
H3PO4
O
(Z)
51. Answer (A)
CH2–CH2 O
(C11H12O2) dibasic acid OH OH O
oxidation C C (CH2)2 O
(P must have O
P, Organic acid
multiple bond) O
dacron
dibasic acid must be terephthalic acid i.e.
COOH
to give dacron, compound must have benzene based structure
COOH
Ozonolysis
C11H12O2 ketone + oxidized products of benzene.
COOH
Possible structure of P is (C111H12O2)
COOH COOH
O
oxidation
+
COOH
(P)
COOH
ozonolysis
O
+ oxidized product
ketone
(P)

O O Me
COOH COOH C–Cl C–Me H–C–OH
H 2/Pd-C SOCl2 MeMgBr, CdCl2 NaBH 4
(P) (Q)
Me Me
–
CH–OH CH–Cl Me–CH Mg+2 Cl – Me–CH–COOMgCl Me–CH–COOH
+
HCl Mg, Et2 O CO2 H 3O
(Q) (R)
52. Answer (B)

 –
COOH COOH CONH 2 NH2 N C NH CH 3
H2 /Pd-C NH3 / Br2 /NaOH CHCl3/KOH H2 /Pd-C
53. Answer A(p, s); B(q); C(q, r, s); D(q, r)

54. Answer A(p, q, s, t), B(s, t), C(p), D(r)
(A) CH3CH2CH2CN will give mentioned reaction with other reagents.
(B) Esters will be reduced by DIBAL-H and it will be hydrolyzed by alkaline hydrolysis.
(C) Alkenes are only reduced by catalytic hydrogenation.
(D) Primary amines will give +ve carbyl amine test with NaOH and CHCl3.
 
O
NaOH
CH3CH2CH2CH2 — NH2 
CHCl
 CH3 CH2 CH2CH2 — N  C
3
Carbyl amine
55. Answer A(p, q, t); B(p, s, t); C(r, s); D(p)
NCl
SN2
Br
O
(A)
O E2
(B) OH ZnCl 2/HCl Cl [Nucleophilic substitution]
(RCO) 2O
O
C
O R

A and B can undergo dehydrogenation.
HO NCl
C
NCl H
O
OH
C
(C) H
O
OH O O
C
R C O C R H
O
O R
Br 
Nu
Nu
(D) (SNAr)
NO2 Mechanism NO2
56. Answer A(r, s); B(t); C(p, q); D(r)
(A) NN + O—H

Cl–
OH
N=N O
H
N=N O
 Coupling reaction and electrophilic substitution reaction.
OH OH OH OH2
+H
(B) CH3 — C — C — CH3 CH3 — C — C — CH3
CH3 CH3 CH3 CH3
O CH3 OH
CH3
CH3 — C — C — CH3 CH3 — C — C
CH3
CH3 CH3
Carbocation intermediate

O OH
O +
LiAlH4 H H3O
(C) C Nucleophilic addition
C H C H
CH3
CH3 CH3
Racemic mixture
Nucleophilic
H Base S substitution S
(D)
S Cl Cl
B
57. Answer A(r, s, t), B(p, s), C(r, s), D(q, r)
O O
H CH2 H2C
O O O O
OH Nucleophilic addition
A.
Carbanion
O OH O
Dehydration HO – H
–H2O
O Cl
Cl O O
B. CH3MgBr Nucleophilic
CH3 substitution CH3
Carbanion
Nucleophilic
addition
H
..
.O
. O H H
18 18 18
H–O H–O O  H–O O O
–H
Nucleophilic +H Dehydration
C. addition
H
+H Electrophilic
D. OH Dehydration substitution
H
Me Me
58. Answer (A)
O O
(1) C6H5CH2 – C – O CH3 C6H5CH2 + CO2 + CH3 – O

O CH3 CH3
O
(3) C6H5CH2 – C – O C CH3 CO2 + C6H5CH2 + CH3 – C – O
CH2 – C6H5 CH2 – C6H5
O
C O CH3 O CH3
(4) C6H5 O C – CH3 C6H5 – C – O + O – C – CH3

CH3 CH3
O O
C O C
(2) C6H5 O CH3 C6H5 O + CH3 – O
59. Answer (D)
h
Br2 Br + Br
CH3 CH2
+ Br + HBr
CH2 CH2 – Br
+ Br2 + Br
60. Answer (C)
COO–Na+
NaOH
C CH3 Br2 + CHBr3
O
H2O/H+
COOH
It is haloform reaction.
61. Answer (C)
O
CH3 – C
O
CH3 – C
CH = O CH = CH – COOH
O
CH3 COOK
Cinnamic acid
It exists in two geometrical forms.
C –H C –H
H – C – COOH HOC – C – H
Trans O
isomer Cis isomer
It is basic example of Perkin's reaction.

62. Answer (D)
Ph Ph O O
Me Ph
I2/NaOH
(P) HO + H2SO4 Me Me C – OH
Ph HO Me Ph Me Ph
O
Ph
NaOBr
Me C – OH
Ph
P  1, 5
Ph Ph O Ph
H [Ag(NH3)2]OH
(Q) H2N OH + HNO2 Me Me COOH
Ph Me Ph H Ph
Ph
Fehling
Me COOH
Solution
Ph
Q  2, 3
Ph Ph O
Ph
(R) HO OH + H2SO4 Ph
Me Me Me Me
NaOBr I2/NaOH
Ph Ph
Me COOH Me COOH
Ph Ph
R  1, 5

Ph Ph
Ph
(S) Ph OH + AgNO3 Ph CHO
Br Me Me
Fehling [Ag(NH3)2]OH
solution
Ph Ph
Ph COOH Ph COOH
Me Me
S  2, 3
63. Answer (A)
Cl KCN CN +
H 3O / COOH LiA H 4
(III)
CO 2CH3 CO 2CH3 CO 2H
Conc.
CH2OH H 2SO 4 CH2 OH –H 2 O
:
+ –H
+
O
CH2 OH CH2 OH2
(Q) (R)
CH2OH
CO2Me CH2OH Conc.
LiAH4 H2SO4
+
(IV)
CH2Me CH2OH CH2—OH2
(Q)
+ –H
+
O—H O
(R)
(III), (Q), (R) ; (IV), (Q), (R)

64. Answer (B)
CN DIBAL-H CHO dil. HCl CHO NaBH 4 CH 2OH

(I)
O O
CHO CH 2OH
O O
(Q)
+
Conc. CH2 OH2 –H
+
H2 SO 4 + O O
CH2 OH 2 H
(R)

OH Conc.
(i) O3 CHO NaBH4 H2SO4
(II)
(ii) Zn/H2O O
COOH COOH COOH
O
(P) (S) (U)
(I), (Q), (R); (II), (P), (S), (U)

65. Answer (1)
O
O
1. O3 1. NaOH(aq)
2. Zn–H2O 2. Heat
66. Answer (4)

Carboxylic acids and aromatic alcohols dissolves in aqueous NaOH.
COOH OH OH COOH
, , ,
N
H3C CH3
will be soluble in aqueous NaOH.

67. Answer (2)
O O O O O
+
OH
H3O OH *
O (–H2O, –CO2)
OH
O O O O O
O
HOOC (i) O3
HOOC (ii) H2O2
O (P)
So, final product (P) has two carboxylic acid

 Heating causes evaporation of water and due to which concentration of acid increases and in concentrated
acidic medium decarboxylation as well as dehydration will take place.

68. Answer (5)
O
1 2 3 4
(I) CH3 CH2 CH2 CH2 C CH3
5 6
(II) CH3 CH2 CH2 C CH2 CH3
CH3 O
(III) CH3 CH2 CH C CH3

It has chiral centre
CH3 O
(IV) CH3 CH C CH3
CH3
CH3 O
(V) CH3 CH C CH2 CH3
(VI) CH3 CH CH2 C CH3
CH3
Only (III) form diastereomers on addition reaction so, desired ketones as per addition reaction is 5.
69. Answer (4)
CHO
CO, HCl
(Gatterman Koch Reaction)
Anhyd AlCl3/CuCl
OH
CHCl2 CH CHO
H2O OH
100°C –H2O
COCl CHO
H2
(Rosenmund Reduction)
Pd–BaSO4
COOMe CHO
DIBAL–H
Toluene, –78°C H2O

70. Answer (18.00)
Degree of unsaturation of Q = 18
71. Answer (1.62)
72. Answer (3.20)
Sol. of Q. No. 71 and 72
H 2O NaNH 2
Mg2C3 C3H 4 (P) CH3 C C CH 3
4g MeI
(Q)
Hg2+/H + Red hot

iron tube
O
CH3 C CH 3 (S)
Ba(OH)2/ (R)
O
CH 3 C CH C CH3
CH3
(T)
NaOCl
O
CH 3 C CH C OH (U) + CHCl 3
CH3
4 g of C3H4 = 0.1 mol

From 0.1 mol of P, 0.01 mol of R will be produced
 1.62 g of R is produced
From 0.1 mol of P, 0.032 mol of U is produced
= 3.2 g of U is produced


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Chapter 24

Aldehydes, Ketones and Carboxylic Acids

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456

10. Answer (A)

(II) (stabilizes by H-bonding)

 Acidity order is I > II > III > IV.

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11. Answer (A)

12. Answer (B)

III. MeO COOH

IV. H3 C  CH2  COOH

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15. Answer (A, C, D)

H3C H3C H3C

Hence answer is (A, C, D).

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17. Answer (C)

Reaction I : C Br2 (1.0 mol)

CH3 CH3 Undergoes

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21. Answer (A, B, D)

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22. Answer (B, D)

OMe OMe AgNO3, NH4OH

OMe OMe OMe

CH3 H C CH3 CH 3 H C CH3

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Compound (S) can not decolorizes bromine water.

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28. Answer (B)

H2/Pd, BaSO4 , quinoline

(cis product) (L)

32. Answer (B)

Conc. H2SO4 dehydration

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35. Answer (B)

41. Answer (C)

(CH3CO)2 O (i) H2 , Pd/C

43. Answer (B)

44. Answer (A)

45. Answer (A)

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46. Answer (B)

49. Answer (C)

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50. Answer (A)

51. Answer (A)

dibasic acid must be terephthalic acid i.e.

to give dacron, compound must have benzene based structure

Possible structure of P is (C111H12O2)

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52. Answer (B)

53. Answer A(p, s); B(q); C(q, r, s); D(q, r)

(B) OH ZnCl 2/HCl Cl [Nucleophilic substitution]

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A and B can undergo dehydrogenation.

56. Answer A(r, s); B(t); C(p, q); D(r)