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 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions

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ORGANIC CHEMISTRY
CARBONYL COMPOUND
1. In the following reactions, P, Q, R, and S are the major products. [JEE(Advanced) 2023]
(i) PhMgBr, then H O⊕
CH3CH 2 CH(CH3 )CH 2 CN  3
(ii) PhMgBr, then H O
→P
2

O
|| (i) anhyd. AlCl3
Ph – H + CH3CCl Q
(ii) PhMgBr, then H2O

O
|| 1
(i) (PhCH ) Cd
2 22
CH3CH2CCl R
(ii) PhMgBr, then H O
2

( i ) PhMgBr, then H 2O

PhCH 2 CHO 

(ii) CrO3 , dil.H 2SO 4
(iii) HCN
→S
(iv) H 2SO4 , ∆

The correct statement(s) about P, Q, R, and S is(are)

(A) Both P and Q have asymmetric carbon(s).
(B) Both Q and R have asymmetric carbon(s).
(C) Both P and R have asymmetric carbon(s).
(D) P has asymmetric carbon(s), S does not have any asymmetric carbon.
2. In the reaction scheme shown below Q, R and S are the major products. [JEE(Advanced) 2020]
O
CH3
H3C H3C CH3 O
H3C (i) CH3MgBr
O (i) Zn-Hg/HCl (ii) H3O+
Q R S
AlCl3 (ii) H3PO4 (iii) H2SO4/∆
P
The correct structure of
CH3 CH3
H3C H3C
H3C CH3 H3C CH3
H3C H3C
(A) S is (B) Q is

CH3 HO2C O
CH3 CH3
H3C H3C
H3C CH3 H3C CH3
H3C H3C

(C) R is (D) S is H3C

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
3. Choose the correct option(s) for the following set of reactions [JEE(Advanced) 2019]

C6H10 O  →
i) MeMgBr
Q  →
Conc. HCl
S
ii) H2O
(major)
20% H3PO 4, 360 K

i) H , Ni
T ← 2
 R 
ii) Br2, h ν ∆ → U
HBr, benzoyl peroxide

(major) (major) (major)

H3C Br CH3 CH 3
H3C Cl
Cl Br
(A) (B)

U S S U

CH3 H3C Br CH3 H3C Br

Cl Br
(C) (D)

S T U T

4. The reaction(s) leading to the formation of 1,3,5-trimethylbenzene is (are) [JEE(Advanced) 2018]

O
Conc. H2SO4 heated iron tube
(A) (B) Me H
∆ 873 K
O
1) Br2 , NaOH CHO
2) H3O+
(C) (D) Zn/Hg, HCl
3) sodalime, ∆
OHC CHO
O O
5. In the following reaction sequence, the amount of D (in g) formed from 10 moles of acetophenone
is_______.
–1
(Atomic weight in g mol : H = 1, C = 12, N = 14, O = 16, Br = 80. The yield (%) corresponding to the
product in each step is given in the parenthesis) [JEE(Advanced) 2018]
O

NaOBr NH3 , ∆ Br 2 /KOH Br 2 (3 equiv)

A B C D
+
H3O (60%) (50%) (50%) AcOH (100%)

6. Positive Tollen's test is observed for [JEE(Advanced) 2016]

H O OH
CHO Ph O
(A) H (B) (C) Ph (D)
H O Ph Ph
H

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
 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
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7. The major product of the following reaction sequence is : [JEE(Advanced) 2016]
O

(i) HCHO (excess) / NaOH, heat

+
(ii) HCHO / H (catalytic amount)

O OH
O O O O OH O O
HO
(A) (B) (C) (D)

OH
8. Reagent(s) which can be used to bring about the following transformation is(are)
[JEE(Advanced) 2016]

O O O O
C O C

H OH
COOH O COOH O
(A) LiAlH4 in (C2H5)2O (B) BH3 in THF
(C) NaBH4 in C2H5OH (D) Raney Ni / H2 in THF
9. The major product of the following reaction is - [JEE(Advanced) 2015]
O

I. KOH, H2O
CH3
II. H+, Heat
O

CH3 CH3
O
O O O
CH3 CH3
(A) (B) (C) (D)

10. Among the following the number of reaction(s) that produce(s) benzaldehyde is –
[JEE(Advanced) 2015]
CO,
CO, HCl
HCl
I.
Anhydrous AlCl33/CuCl
Anhydrous AlCl /CuCl
CHCl
CHCl22
II. H
H22O
100°C
COCl
COCl
III. H22
Pd-BaSO
Pd-BaSO44
CO
CO2Me
Me
DIBAL-H
DIBAL-H
IV.
Toluene,–78ºC
Toluene, –78°C
H22O
H O

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
Paragraph For Questions No. 11 and 12
In the following reaction [JEE(Advanced) 2015]
Pd-BaSO4 (i) B2H6
C8H6 C8H8 X
H2 (ii) H2O2, NaOH, H2O

H2O
HgSO4, H2SO4

(i) EtMgBr, H2O

C8H8O + Y
(ii) H , heat

11. Compound X is :
O OH
OH

CH33 CH3
(A) (B)

OH
OH CHO
CHO
(C) (D)

12. The major compound Y is :

CH33 CH33
(A) (B)

CH
CH33
CH
CH22
CH33 CH
CH33
(C) (D)

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
 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
®
SOLUTIONS
1. Ans. (C, D)
Sol. Formation of P
PhMgBr Ph
CH 3 – CH2 – CH – CH2 – CN
H3 O + C
CH 3 O

PhMgBr
then H3 O +

Ph
*
Ph
Asymmetric OH
carbon
(P)

Formation of Q
O O
anhy. AlCl3
+ CH 3 – C – Cl Ph – C – CH3
PhMgBr
then H3 O +

OH

Ph – C – CH3

Ph
(Q)
No asymmetric carbon

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®

Formation of R

C – Cl + 1 (Ph – CH2 )2 Cd Ph
2
O O
PhMgBr
then H3 O +

Ph

* Ph
asymmetric OH
carbon
(R)

Formation of S
PhMgBr
Ph – CH 2 – C – H Ph – CH 2 – CH – Ph
H3 O +
OH
O
CrO3 with dil. H2 SO4

Ph – CH 2 – C – Ph

O
HCN

OH
H2 SO4
Ph – CH = C – Ph Ph – CH 2 – C – Ph
∆
COOH CN
(S) No asymmetric carbon

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
 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
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2. Ans. (B, D)
O

Sol. O
AlCl3

(P)
C=O

HO
(Q)
O
Zn/Hg/HCl

H3PO4
HO
O
O=C

(R)

(1) CH3MgBr
(2) H+/H2O

H2SO4
HO ∆

CH3
(S)

3. Ans. (B, D)
Sol.
O OH Cl

1. CH3 MgBr conc. HCl

2. H2O
Q S

Br Me
Br
(i) H2, Ni HBr, benzoyl peroxide
(ii) Br2, hv
T R U

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
4. Ans. (A, B, D)

Sol. (A) →

Conc H 2SO4
∆

(B) →
Fe∆

(C) →
(1)Br2 NaOH
(2)H O⊕ →
(3)Soda lim e
∆
3

(D) 
ZnHg,HCl
→

5. Ans. (495)

O HO O H2N O NH2 NH2

Br Br
NaOBr NH3, ∆ Br2 /KOH Br2 (3 equiv)
Sol. +
H 3O AcOH
10 mol (60%) (50%) (50%)
6 mol 3 mol 1.5 mol Br
(100%)
1.5 mol = 495 gm
6. Ans. (A, B, C)
Sol. Tollens's test is given by compounds having aldehyde group. Also α-hydroxy carbonyl gives positive
tollen's test.
H
Tollen's –
H C =O H CO22–
CO
reagent + Ag mirror
(A) H H (+ve test)
H H
Acraldehyde

––
CH=O CO22
CO
Tollen's
(B) + Ag mirror (+ve test)
reagent

Benzaldehyde

Ph–CH–C–Ph Tollen's
Ph–C–C–Ph + Ag mirror
(C) reagent (+ve test)
OH O O O
Benzoin
Tollen's
(D) PhCH=CH–C–Ph No reaction (–ve test)
reagent
O

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
 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
®
7. Ans. (A)
Sol.
OH OH
O O OH
O CH2 O CH2
H–C–H / NaOH H–C–H / NaOH –
H [Cross aldol reaction] + HCOO
[Cross cannizaro
reaction]

OH
OH O O
CH2 O
+
H–C–H / H
Acetal formation

8. Ans. (C, D)

O O O O
Sol. C O C

H OH
O NaBH4 O
CO2H in EtOH CO2H

LiAlH4 in (C2H5)2O ; BH3 in (THF) ; Raney Ni (H2) either can reduce all functional group or can reduce
some of the functional group of the compound given above in reactant side.
But NaBH4 is example of selective reducing agent. It can not reduce –C–O– (ester group) –C–OH ,
O O
(carboxylic acid group), (epoxide group) , but reduces –CH=O (aldehyde group)into –CH2OH
O
(1º alcohol)
9. Ans. (A)
Sol.
O O
1.1.KOH,
KOH, H O
H22O
2. H+, ∆
∆
(Major product)
O
(Aldol condensation product)
Mechanism :

O O O
OH O

O O
H2O

OH H
O ∆/ H + O

-H2O

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
10. Ans. (4)
CH=O
CO , HCl
Sol. I.
Anhydrous AlCl3/CuCl
this reaction is called Gattermann koch synthesis
Cl
CH Cl CH=O
II. H2O
100°C

O O
C CH
Cl H2
III.
Pd-BaSO4
this reaction is called Rosenmund reduction

O O
C Me CH
IV. O DIBAL-H
Toluene ; –78° + MeOH
H2O

11. Ans. (C)

OH
Sol. CH2–C–H
Pd-BaSO4 (1) B2H6
C8H6 H2
C8H8 –
(2) H2O2/OH, H2O
H

D.U. = 6
Aromatic alkyne

H2O
HgSO4, H2SO4

O OH
+
EtMgBr, H2O H

12. Ans. (D)

O
OH
H2O, HgSO4 , H2SO4 EtMgBr, H2O +
Sol. H
Kuchrov reaction

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