Chapter 26

Aldehydes, Ketones and Carboxylic Acids

1. A liquid was mixed with ethanol and a drop of (1) Zn – Hg/HCI (2) Na, Liq. NH3
concentrated H2SO4 was added. A compound with
a fruity smell was formed. The liquid was (3) NaBH4 (4) NH2NH2, OH
[AIEEE-2009]
6. Iodoform can be prepared from all except
(1) HCHO (2) CH3COCH3
[AIEEE-2012]
(3) CH3COOH (4) CH3OH
(1) Isopropyl alcohol
2. Which of the following on heating with aqueous
KOH, produces acetaldehyde? [AIEEE-2009] (2) 3 – Methyl – 2 – butanone

(1) CH3CH2Cl (2) CH2ClCH2Cl (3) Isobutyl alcohol

(3) CH3CHCl2 (4) CH3COCl (4) Ethyl methyl ketone

3. In Cannizzaro reaction given below 7. An organic compound A upon reacting with NH3
gives B. On heating, B gives C. C in presence of
: OH KOH reacts with Br2 to give CH3CH2NH2. A is
:

2PhCHO PhCH2OH + Ph CO 2
[JEE (Main)-2013]
the slowest step is [AIEEE-2009]
(1) CH3COOH
(1) The transfer of hydride to the carbonyl group
(2) CH3CH2CH2COOH
(2) The abstraction of proton from the carboxylic
group (3) CH3 CH COOH
(3) The deprotonation of PhCH2OH
CH3
(4) The attack of : OH at the carboxyl group
(4) CH3CH2COOH
4. Ozonolysis of an organic compound ‘A’ produces
8. The most suitable reagent for the conversion of
acetone and propionaldehyde in equimolar mixture.
R – CH2 – OH  R – CHO is [JEE (Main)-2014]
Identify ‘A’ from the following compounds
(1) KMnO4
[AIEEE-2011]
(1) 2 - Methyl - 2 - pentene (2) K2Cr2O7

(2) 2 - Methyl - 1 - pentene (3) CrO3

(3) 1 - Pentene (4) PCC (Pyridinium Chlorochromate)

(4) 2 - Pentene 9. In the reaction,
5. In the given transformation, which of the following LiAlH4 PCl
Alc.KOH
is the most appropriate reagent? [AIEEE-2012] CH3COOH   A 
5
B   C,
Reagent the product C is [JEE (Main)-2014]
CH = CHCOCH3
(1) Acetaldehyde
HO
(2) Acetylene
CH = CHCH2CH3
(3) Ethylene
HO (4) Acetyl chloride

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10. In the following sequence of reactions : O O

O O
KMnO SOCl H /Pd (3) and O
Toluene 
4
A 
2
 B 
2
BaSO
 C, O Br
4

the product C is [JEE (Main)-2015] OH OH

(4) and
(1) C6H5COOH (2) C6H5CH3 OCH3 OCH3
(3) C6H5CH2OH (4) C6H5CHO O O
Br
11. Which of the following, upon treatment with 14. The compounds A and B in the following reaction
tert-BuONa followed by addition of bromine water, are, respectively [JEE (Main)-2019]
fails to decolourize the colour of bromine?
[JEE (Main)-2017]
HCHO + HCI AgCN
A B
O
O
(1) (2) (1) A = Benzyl alcohol, B = Benzyl isocyanide
Br Br (2) A = Benzyl chloride, B = Benzyl cyanide

C6H5 (3) A = Benzyl chloride, B = Benzyl isocyanide

O
(3) (4) (4) A = Benzyl alcohol, B = Benzyl cyanide
Br Br
15. The major product of following reaction is
12. The major product obtained in the following reaction
is [JEE (Main)-2017] (1) AIH(i-Bu)2
R C N ? [JEE (Main)-2019]
(2) H 2O
O
O (1) RCH2NH2 (2) RCHO
(3) RCONH2 (4) RCOOH
DIBAL-H
16. The correct match between Item I and Item II is
Item I Item II
COOH
(A) Benzaldehyde (P) Mobile phase
CHO CHO (B) Alumina (Q) Adsorbent
(1) (2)
COOH CHO (C) Acetonitrile (R) Adsorbate

OH OH [JEE (Main)-2019]
(1) (A)  (Q), (B)  (R), (C)  (P)
(3) CHO (4) CHO (2) (A)  (Q), (B)  (P), (C)  (R)
COOH CHO (3) (A)  (P), (B)  (R), (C)  (Q)
13. Phenol reacts with methyl chloroformate in the (4) (A)  (R), (B)  (Q), (C)  (P)
presence of NaOH to form product A. A reacts with
17. The major product formed in the following reaction is
Br2 to form product B. A and B are respectively
[JEE (Main)-2018] O CH3
O
OH Br OH
(1) and H+ dil. NaOH
OCH3 OCH3 H 3C

O O [JEE (Main)-2019]
O O O O O OH
(2) and
O O
(1)
H3C
Br

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OH O
(2) O2N COOC2H5
H 3C H
O OH III

(3) H CH 3O COOC 2H 5
H3C

OH IV
O
[JEE (Main)-2019]
(4) H3C
(1) III > II > IV > I (2) IV > II > III > I
(3) II > III > I > IV (4) III > II > I > IV
18. The major product ‘X’ formed in the following
reaction is 21. An aromatic compound ‘A’ having molecular
formula C7H6O2 on treating with aqueous ammonia
O O and heating forms compound ‘B’. The compound
|| ||
CH2—C—OCH3 ‘B’ on reaction with molecular bromine and
NaBH4 potassium hydroxide provides compound ‘C’ having
X molecular formula C6H7N. The structure ‘A’ is
MeOH
[JEE (Main)-2019]
[JEE (Main)-2019]
(1) OHC
OH OH O
CH2CH2OH CH2 C OCH3
OH
(1) (2)

O O OH
CH2 C H CH2CH2OH (2) CH == CH — CHO
(3) (4)
COOH
19. Which dicarboxylic acid in presence of a dehydrating (3)
agent is least reactive to give an anhydride?
[JEE (Main)-2019]
CHO
COOH CO 2H
(1) (2) (4)
COOH CO 2H OH
O 22. The major product obtained in the following reaction
CH2
CH2 CH2
is
COOH OH
(3) (4)
CH2 COOH CH2 OH CO 2Et NaOEt/
CH2 
O O
O
20. The decreasing order of ease of alkaline hydrolysis [JEE (Main)-2019]
for the following esters is
O
(1)
COOC 2H5

CO2Et
I

Cl COOC 2H 5 O
(2)
CO 2Et
II

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O H
(3)
CO 2Et O
(1)
CHO
O
(4) NH
(2)
CO2Et

23. The major porduct of the following reaction is OH

O
(3)
NH2
CH3N NaBH 4

[JEE (Main)-2019] N
(4)
OH
(1) CH3N
26. Which of the following compounds reacts with
OH ethylmagnesium bromide and also decolourizes
(2) CH3N bromine water solution? [JEE (Main)-2019]
O CN
(3) CH3NH CH 2 — CO 2CH 3

OH (1)
(4) CH3NH

24. The major product of the following reaction is OH

COCH3
(i) KMnO 4/KOH,  (2)
(ii) H2SO 4(dil)
CH3
CN O
[JEE (Main)-2019]

COCOOH (3)
(1)
HOOC
OCH 3
COOH
CH
(2) (4) CH 2
HOOC
COOH
27. In the following reaction
(3)
HCI
OHC Aldehyde + Alcohol Acetal
COCH3 Aldehyde Alcohol
(4) HCHO tBuOH
HOOC
CH3CHO MeOH
25. The major product of the following reaction is:
The best combination is [JEE (Main)-2019]
O
(1) HCHO and MeOH
OEt (i) Ni/H2
(2) HCHO and tBuOH
CN (ii) DIBAL–H
(3) CH3CHO and tBuOH
[JEE (Main)-2019]
(4) CH3CHO and MeOH
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28. In the following reactions, products A and B are O

O O (B) C2H5 OCH3

dil NaOH
H3C H [A]
H 3C CH3 O

(C) C2H5 Cl
+
H3O
[A] [B] [JEE (Main)-2019]

O O
O O (D) C2H5 O C2H5
CH3 CH3
(1) A = CH3 ;B= CH3 [JEE (Main)-2019]
HO
(1) (A) < (B) < (C) < (D)
O O
CH3 CH3 (2) (B) < (A) < (D) < (C)
(2) A = CH3 ;B= CH3
(3) (A) < (B) < (D) < (C)
HO
(4) (B) < (A) < (C) < (D)
O
O
OH 31. The aldehydes which will not form Grignard product
C CH3
H3C H H with one equivalent Grignard reagent are
(3) A = ;B=
H3C H 3C CHO
CH3 CH3
(A)
O O
OH H 2C
H H CHO
H3C
(4) A = ;B=
H3C
CH3
H 3C
CH3 (B) HO2C
CHO
29. The major product of the following reaction
CN (C) H3CO

CHO
O (ii) H3O+

O (D) HOH2C

[JEE (Main)-2019] [JEE (Main)-2019]

(1) (B), (C)
CHO CHO
(2) (B), (D)
(1) (2)
O OH (3) (B), (C), (D)
O CHO (4) (C), (D)

32. The major product of the following reaction is

CH = NH CHO
(3) (4) H3C O
NH2
OH O O
OH
+
(i) NaNO2/H
+
30. The increasing order of the reactivity of the following (ii) CrO3/H [JEE (Main)-2019]
with LiAlH4 is (iii) H2SO4 (conc.),

O HO
(1)
(A) C2H5 NH2
O
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CH3 O 35. An organic compound neither reacts with neutral

(2) ferric chloride solution nor with Fehling solution. It
O however, reacts with Grignard reagent and gives
O
positive iodoform test. The compound is
O [JEE (Main)-2019]
HO O
(3)
C2 H5
(1)
CH 3
O O
O
CH3 O CH 3
(4) (2)
H
O
O
33. The major product of the following reaction is
OH
O
Br NaBH 4 CH 3
(3)
MeOH, 25°C C2 H5

O
[JEE (Main)-2019] O
OH CH 3
Br (4)
OH
(1)
36. The major product obtained in the following reaction
is
OH
OMe
CH3 O
(2)
NaOH
OHC 

O [JEE (Main)-2019]
(3) CH3
H3C
(1) H (2) H
OMe
O O
(4) CH2 CH3

34. An organic compound ‘X’ showing the following CH3 CH3

solubility profile is
water (3) (4)
insoluble
X 5% HCl
insoluble O O
10% NaOH 37. The major product of the following reaction is
soluble
10% NaHCO3 LiAlH
insoluble CH3 CH  CHCO2CH3 
4


[JEE (Main)-2019] [JEE (Main)-2019]

(1) Benzamide (1) CH3CH2CH2CH2OH

(2) Oleic acid (2) CH3CH2CH2CHO

(3) o-Toluidine (3) CH3CH2CH2CO2CH3

(4) m-Cresol (4) CH3CH = CHCH2OH

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38. The major product of the following reaction is 41. The major product ‘Y’ in the following reaction is:
Ph CH3
OH NaOCI (i) SOCI2
X Y
CH 2OH H 2 SO4 (cat.) O (ii) aniline
CHCl3
[JEE (Main)-2019]
CO 2Et
Ph
[JEE (Main)-2019] NH2 N
O
O
O OH (1) (2)
Ph
(1) (2)
O O NH2
CO2Et
O
O HN Ph
OH
(3) (4)
(3) (4)
OEt O Ph
COOH
O 42. Compound A (C9H10O) shows positive iodoform
39. In the following reaction test. Oxidation of A with KMnO 4 /KOH gives
acid B (C8H6O4). Anhydride of B is used for the
HCl


carbonyl compound  MeOH  acetal preparation of phenolphthalein. Compound A is:
[JEE (Main)-2019]
Rate of the reaction is the highest for
CH3 CH3
[JEE (Main)-2019]
(1) (2)
CH3
(1) Acetone as substrate and methanol in excess
(2) Propanal as substrate and methanol in O
O CH3
stoichiometric amount
O
(3) Propanal as substrate and methanol in excess
(4) Acetone as substrate and methanol in CH3 CH2 – C – H
stoichiometric amount (3) (4)
O
CH3
40. Major products of the following reaction are :
43. The major product of the following reaction is
CHO (i) 50% NaOH
+ HCHO +
(ii) H3O
HO (1) CrO3

[JEE (Main)-2019] (2) SOCI2/

HO (3) 
CH2OH [JEE (Main)-2019]
(1) HCOOH and
O O

CH2OH COOH (1) (2)

(2) and
CI HO
O O
COOH
(3) CH3OH and (3) (4)

(4) CH3OH and HCO2H HO Cl

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44. What is the product of following reaction? 47. An unsaturated hydrocarbon X absorbs two
hydrogen molecules on catalytic hydrogenation, and
(i) NaBH
Hex – 3 – ynal 
(ii)PBr
4
? also gives following reaction
3
(iii)Mg/ether
(iv) CO2 /H3O O [Ag(NH ) ]
X 3
Zn/H O
 A 
3 2

2

[JEE (Main)-2020]
B(3-oxo-hexanedicarboxylic acid)
(1) COOH
X will be [JEE (Main)-2020]

(2) COOH

(3) COOH (1) (2)

(4)
COOH O
45. A solution of m-chloroaniline, m-chlorophenol and m-
chlorobenzoic acid in ethyl acetate was extracted (3) (4)
initially with a saturated solution of NaHCO3 to give
fraction A. The left over organic phase was extracted
48. Identify (A) in the following reaction sequence.
with dilute NaOH solution to give fraction B. The final
organic layer was labelled as fraction C. Fractions (A) 
3

(i) CH MgBr
(B) 
3 2 O /Zn, H O

A, B and C, contain respectively : Gives (ii) H , H2O
Positive (iii) Conc. H2SO4 / 
[JEE (Main)-2020] iodoform
test
(1) m-chloroaniline, m-chlorobenzoic acid and m- O
chlorophenol C
H
(2) m-chlorophenol, m-chlorobenzoic acid and m-
chloroaniline CH3

(3) m-chlorobenzoic acid, m-chlorophenol and m- H3C C O

chloroaniline CH3

(4) m-chlorobenzoic acid, m-chloroaniline and m- [JEE (Main)-2020]

chlorophenol
CH3
46. The most suitable reagent for the given conversion
is (1)
CONH 2 CH 3 CH3
O
C ==O CH3
?
CH3
HO2 C
(2)
CN
O CH3

CONH 2 CH3
COCH3

(3)
HOH2 C
O CH3
CN
[JEE (Main)-2020]
(1) LiAIH4 (2) NaBH4 (4)
(3) H2/Pd (4) B2H6 O CH3

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49. The major product (Y) in the following reaction is CHO

CH3 (iii)
HgSO4, H2SO4 OCH3
CH3–CH–C CH X
H2O

(i) C2H5MgBr, H2O O2N CHO

(ii) Conc. H2SO4/
Y [JEE (Main)-2020] (iv) [JEE (Main)-2020]

CH3
(1) CH3–CH–C=CH–CH3 (1) (iii) < (iv) < (ii) < (i)

CH3 (2) (iii) < (i) < (iv) < (ii)

(3) (iii) < (iv) < (i) < (ii)
CH3
(4) (i) < (iii) < (iv) < (ii)
(2) CH3–C=C–CH3
52. The increasing order of the reactivity of the following
CH2CH3 compounds in nucleophilic addition reaction is
CH2 Propanal, Benzaldehyde, Propanone, Butanone
(3) H3C–C–CH–CH3 [JEE (Main)-2020]
C2H5 (1) Propanal < Propanone < Butanone <
CH3 Benzaldehyde
(2) Benzaldehyde < Propanal < Propanone <
(4) CH3–CH–C=CH2
Butanone
CH2CH3
(3) Benzaldehyde < Butanone < Propanone <
50. In the following reaction A is Propanal
H O (4) Butanone < Propanone < Benzaldehyde <
Propanal
(i) Br2, h 53. The compound A in the following reactions is
(ii) KOH (alc.)
A (i) CH MgBr/H O
(iii) O3 A 
3 2

(ii) Conc. H2SO4 / 
(iv) (CH3)2S
(i) O
(v) NaOH (aq) +  B 
3
C D
(ii) Zn/H2O
[JEE (Main)-2020]
(i) Conc. KOH
C   +
COO K + CH 2OH
(ii) 

(1) (2) CH3 O

I II
Ba(OH)2
D  H3 C  C  CH  C  CH3


[JEE (Main)-2020]
O
(3) (4) II
(1)
C6H5  C  CH2CH3

51. The increasing order of the following compounds O

towards HCN addition is (2) II
C6H5  C  CH3
H3CO CHO
O
(i)
(3) II
C6H5  CH2  C  CH3
CHO O
II CH3
(ii) (4) C6 H5  C CH
NO2 CH3

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54. An organic compound (A) (molecular formula (1)

C6H12O2) was hydrolysed with dil. H2SO4 to give a
carboxylic acid (B) and an alcohol (C). ‘C’ gives
(2)
white turbidity immediately when treated with
anhydrous ZnCl 2 and conc. HCl. The organic
compound (A) is [JEE (Main)-2020]
(3)
O O
(1) (2) O
(4)
O
57. The correct match between Item-I (starting material)
O O and Item-II (reagent) for the preparation of
(3) (4) benzaldehyde is
O O

55. [P] on treatment with Br2/FeBr3 in CCl4 produced Item-I Item-II

a single isomer C8H7O2Br while heating [P] with (I) Benzene (P) HCl and SnCl2,
sodalime gave toluene. The compound [P] is
H3O+
[JEE (Main)-2020]
COOH COOH (II) Benzonitrile (Q) H2, Pd-BaSO4, S

CH3 and quinoline

(1) (2) (III) Benzoyl Chloride (R) CO, HCl and AlCl3
CH 3
[JEE (Main)-2020]
COOH CH 2COOH
(1) (I) - (R), (II) - (P) and (III) - (Q)

(3) (4) (2) (I) - (P), (II) - (Q) and (III) - (R)

(3) (I) - (Q), (II) - (R) and (III) - (P)

CH3 (4) (I) - (R), (II) - (Q) and (III) - (P)
56. Consider the following reactions
58. Consider the following reactions[JEE (Main)-2020]
ozonolysis
'A'  'B ' ' C '
(C7H14 )
(i) CH MgBr
Cu
A 
3
  B 
573 K
 2  methyl  2  butene
(I2 + NaOH) (ii) H3O
‘B’ yellow ppt
 The mass percentage of carbon in A is ______ .
[JEE (Main)-2020]
(Ag2O)
silver mirror 59. The number of chiral centres present in [B] is
 _____.
(I2 + NaOH)
no yellow ppt (i) C2 H5 MgBr
‘C’  CH C N +
[A]
(ii) H3 O
gives white
LiAlH4 Anhydrous ZnCl 2 turbidity CH 3
‘D’ & Conc. HCl within
5 minutes (i) CH3 MgBr
[B] [JEE (Main)-2020]
‘A’ is [JEE (Main)-2020] (ii) H 2O

  
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