QUANTA CHEMISTRY

An Institute of Chemical Sciences

CSIR-NET | IIT-GATE | IIT-JAM | Other MSc. Entrance

DPP- (12) Name Reaction (JAM)

1. Write the major product –
O
DMSO
CH3CCH3 + Ph3P CHCH2CH2CH2CH3

H3C H H3C
(a) C C H2 H2 (b) C CH(CH2)3 CH3
H H2C C C CH3 H3C

H3C H2 H2
(c) CH C C C C CH3 (d) All products are possible
H3C H H

2. Which of the following statement is correct for the following reaction –

C6H5CHO + CH3CH PPh3
benzene
(a) E is the major product (b) Z is the major product
(c) Both E and Z can be major (d) E is major while Z is minor product.
3. What is the major product –
O
HC(CH2) 7CH 2OAc + CH3CH 2CH2CH2CH PPh3

CH3 CH3
HC C (CH2)3 HC C (CH2)3
H H
H2
(a) (H2C)7 C OAc (b) (H2C)7 CH2OAc

(Z – isomer) (E – isomer)

(CH2)3CH3
C CH2
(c) (H C) CH2OAc (d) Both (a) and (b)
2 7
(Z – isomer)

4. What is the major product –

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 DPP- (12) Name Reaction (JAM)

CHO
benezene
+ Ph3P CHCO2CH2CH3
ref lux
O OH 2h

H H
H
CO2C2H5 CO2C2H5
(a) (b)
O H OH
OH O

H
CO2C2H5 H
H H
(c) COCH2 (d)
O CO2C2H5
C O
OCH3
OC2H5

5. What is the major product

C6H5CHO + Ph3P CHCO2CH2CH3

C6H5 H H H
(a) C C (b) C C
H CO2C2H5 C 6 H5 CO2C2H5

(c) Both (a) and (b) (d) None of these

6. What is the major product for the following reaction.
C6H5CHO + C6H5CH PPh3

H C6H5 C 6 H5 C 6H 5
(a) C C (b) C C
C6H 5 H H H

H C 6 H5
(c) C C (d) Both (a) and (c)
H C6H 5

OH
1. CrO3
Ph
7. O |
2. P(OMe)3 / CH 2  I / n  BuLi
 A
Me
What is the major product and Its formation of selectivity?

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 DPP- (12) Name Reaction (JAM)

Ph Ph

O O
(a) & Chemoselectivity (b) & Chemoselectivity
Me Me
O O
Ph Ph H
(c) & regioselectivity (d) & Regioselectivity
Me Me
O
Me
1. COOMe  CH 2  Cl(excess) / PPh 3 / nBuLi
8. H  (Product / s)

O
The possibility of products formation in all above reaction?
(a) 2 (b) 4 (c) 3 (d) 6

COPh
I
O
1. P(OMe)3 / H2C HC / H3O (Catlytic amount)
O
9. 2. nBuLi
A

CHO
What is the major product A?

COPh COPh O
Ph C C CHO Ph C C HC
H H O

(a) (b) O (c) (d)

HC C CHO HC C HC
H H CH3 CH3
O
O

Ph
 

10. O 
1. P(OMe)3 / CH3 I / tBu O K
A

OEt
Ph

Ph Ph Ph
(a) (b) (c) (d) None of these
O O

OEt OEt OEt

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 DPP- (12) Name Reaction (JAM)
Br
1. P(OMe) 3/ CH2 / tBuOK
O O
11. (excess) (Products)
H
The number of possible products in the above reaction?
(a) 4 (b) 3 (c) 1 (d) 2

O O
O C H O C H
C H C Me
12. (A) (B) (C) (D)

OMe NO2

The order of reactivity of following compounds for wittig reaction?

(a) A > B > C > D (b) A > C > B > D (c) D > A > B > C (d) D > A > C > B

O 1. NaOEt / PPh3
13 A
What is the major product A

(a) (b) (c) (d)

O
O

14. 
1. PPh 3 / CH3CH 2 I / nBuLi
2. BH3 .SMe2 / H 2 O 2 / NaOH
A

What is the major product A?

HO Me HO
OH

(a) (b) (c) (a) and (b) both (d) None of these

15. What is the major product –

DMSO
O + Ph3P CH2

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 DPP- (12) Name Reaction (JAM)

CHO O
(a) (b) (c) (d)

ANSWER KEY

1. (b) 2. (b) 3. (a) 4. (a) 5. (a) 6. (a) 7. (c)

8. (b) 9. (a) 10. (a) 11. (a) 12. (c) 13. (a) 14. (a)
15. (c)

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 DPP- (12) Name Reaction (JAM)

HINTS & SOLUTION

O
H2 H 2 H2 DMSO
C + Ph3P HC C C C CH3
1. H 3C CH3

O P Ph3
O
H 2 H2 H 2 H 3C H H2 H 2 H2
H 3C C C C C C CH3 C C C C C CH 3 + P (Ph)3
H H 3C
H3C
Correct option is (b)
O
benzene
2. C6H5C H + H3C C PPh3
H
Ph3
O O P C6H5 CH3
C 6H 5C H + H3C HC PPh3 C 6H 5C C
CH3
H H
Z
Correct option is (b)

O
H2 H2 H2 H
3. H C (CH2)7 C OAc + H3CH2C C C C PPh3

Ph3
O P CH3
HC CH (CH2)3 CH3 HC CH (CH2)3
(CH2)7 CH2 OAc (CH2)7 CH2 OAc
Z

Correct option is (a)

O
C H
4. benzene
+ Ph3P CH CO2CH2 CH3
O ether
OH

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 DPP- (12) Name Reaction (JAM)

H
O
HC P Ph3 CO2C2H5
HC
CO2CH2 CH3 H
O OH O
OH
E

Correct option is (a)

O
O PPh3
C6H5 C H + Ph3P CH CO2CH2CH 3
5. C6H5 C C CO2C2H5
H
H

C6H5 H
C C E
H CO2C2H5
Correct option is (a)

O C6H5 H
O PPh3
C6H5 C H + C6H5HC PPh3 C C
6. C6H5 C C 6H 5
H C6H5
H
Correct option is (a)
OH
1. CrO3
7. O
2. P(OMe)3/Ph–CH2–I/n-BuLi
Me
OH O P
MeO OMe H2
O CrO3 O OMe P
OMe + Ph C I
MeO
OMe
Me Me

O
OMe O Me O O O
H2 I n-BuLi +
H 2C P OMe Ph C P OMe P P
Ph C OMe Ph C OMe Me
Ph OMe OMe H2 OMe H OMe

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 DPP- (12) Name Reaction (JAM)
O OMe
O O OH O
P OMe
OMe O P
O HC Me Ph
OMe
Ph
Me Me Ph E H
regioselective
Correct option is (c)

O
Me COOMe–CH2–Cl (excess)
8. H PPh3/n-BuLi

O
The possibility of product formation in this reaction
H2 H2 n-BuLi H
MeOOC C Cl + :PPh3 MeOOC C PPh3 MeOOC C PPh3

MeOOC C PPh3
H
Stablised ylide
Product

COOMe MeOOC
O O
Me Me

H H COOMe
COOMe
(1) (2) (3) (4)
O O

Correct option is (b)

COPh H2 H O
1. P(OMe) 3 I C C H3O+
O
9.
2. n-BuLi
CHO

O
H2 H O H O H O
P + I C C MeO P CH2 C P CH2 C
MeO OMe O MeO OMe O MeO OMe O
OMe
I

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 DPP- (12) Name Reaction (JAM)
COPh

O
C Ph COPh
O O CH
n-BuLi H O
P CH C + H O
O P CH C
MeO OMe
MeO O O
O C MeOO CH
H MeO H O
P CH C
MeO O
O
COPh COPh
H3O+

H O
HC CH C HC C CHO
O H
Correct option is (a)

Ph P(OMe)3/CH 3I/BuOK+
10.
O

OEt

O
CH3 O O
t
BuOK+ Ph
P OMe P P
MeO MeO CH3 MeO CH2
OMe I O
OMe OMe
OEt

O
O OMe
O O P
P OMe OMe
OMe Ph
Ph Ph
O O O

OEt OEt OEt

Correct option is (a)

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 DPP- (12) Name Reaction (JAM)

O O P(OMe)3 CH 2 Br t BuOK+ (excess)

11.
H
The number of possible products

O Ph Ph
O O
P
MeO H H
OMe 1 2
Ph Ph
O O

3 4
Correct option is (a)

12. The order of reactivity of the following compounds for wittig reaction?

O O
C H O C H
H C O
C Me
A. B. C. D.

OMe NO 2

D >A> C > B
Correct option is (c)

PPh3
O O O PPh3 O
13 NaOEt

PPh3

PPh3
O

Correct option is (a)

O
1. PPh3/CH3CH2I/n-BuLi
14.
2. BH 3:SMe 2/H2O2/NaOH

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 DPP- (12) Name Reaction (JAM)

O O O PPh3

PPh3/CH 3CH2I/n-BuLi CH
+ H3C CH PPh3 CH 3

HO CH3
H3C CH
BH3; SMe2/H2O2/NaOH

Correct option is (a)

O O O
DMSO P Ph3
15. + Ph3P CH2 C + P (Ph)3
H2
Correct option is (c)

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