Pericyclic Reactions IIT JAM Notes | EduRev

IIT JAM : Pericyclic Reactions IIT JAM Notes | EduRev

 Page 1


ASF
1
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
Single Correct Type
1. Arrange the following in order of increasing rate in Diels-Alder reaction.
(A) (B) 
O
(C) 
O
(D) 
N
(a) A < B < D < C (b) B < C < D < A (c) B < A < C < D (d) B < A < D < C
2.
SO
2
H
3
C
 
methyl
Vinyl ketone
A B
?
? ? ? ? ? ? ? ?
Product B in the above reaction is
(a) 
C
O
CH
3
H
3
C
(b) 
H
3
C
C
H
2
C CH
3
O
(c) 
H
3
C
H
2
C C CH
3
O
(d) 
H
3
C
C CH
3
O
(e) 
C
O
CH
3
H
3
C
3. Major product ‘P’ formed in the reaction given below:
Cl
Br
H
3
C
 
NaI acrylo nitrile conc. HCl
dryether
P ? ? ? ? ? ? ? ? ? ? ? ? ? ?
(a) 
C
H
3
C
NH
2
O
 (b) 
C
H
3
C
NH
2
O
 (c) 
C
H
3
C
OH
O
 (d) 
C
H
3
C
NH
2
O
Daily Assignment Organic Chemistry         IIT-JAM 2015
PERICYCLIC REACTIONS
Ashoka Scienific Forum
Developing Scientific Temper Among Students
IIT-JAM | TIFR | DU | BHU | JNU | ISM | PU & All Other University M.Sc. Entrance Exam
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Page 2


ASF
1
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
Single Correct Type
1. Arrange the following in order of increasing rate in Diels-Alder reaction.
(A) (B) 
O
(C) 
O
(D) 
N
(a) A < B < D < C (b) B < C < D < A (c) B < A < C < D (d) B < A < D < C
2.
SO
2
H
3
C
 
methyl
Vinyl ketone
A B
?
? ? ? ? ? ? ? ?
Product B in the above reaction is
(a) 
C
O
CH
3
H
3
C
(b) 
H
3
C
C
H
2
C CH
3
O
(c) 
H
3
C
H
2
C C CH
3
O
(d) 
H
3
C
C CH
3
O
(e) 
C
O
CH
3
H
3
C
3. Major product ‘P’ formed in the reaction given below:
Cl
Br
H
3
C
 
NaI acrylo nitrile conc. HCl
dryether
P ? ? ? ? ? ? ? ? ? ? ? ? ? ?
(a) 
C
H
3
C
NH
2
O
 (b) 
C
H
3
C
NH
2
O
 (c) 
C
H
3
C
OH
O
 (d) 
C
H
3
C
NH
2
O
Daily Assignment Organic Chemistry         IIT-JAM 2015
PERICYCLIC REACTIONS
Ashoka Scienific Forum
Developing Scientific Temper Among Students
IIT-JAM | TIFR | DU | BHU | JNU | ISM | PU & All Other University M.Sc. Entrance Exam
CSIR-NET | GATE | TIFR
2
ASF
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
4. Product obtained by sigmatropic shift in the given compound is
C
5
H
11
 
sigmatropic shift
?
? ? ? ? ? ?
(a) 
C
5
H
11
(b) 
C
4
H
9
(c) 
C
4
H
9
(d) 
C
5
H
11
5.
O
O
 + 
C
COOCH
3
C
CH
3
 3
H O
A B C
?
? ?
?? ? ?? ? ?? ? ?
Product ‘C’ determined by above series of reactions
(a) 
CH
3
(b) 
COOH
CH
3
(c) 
COOH
COOH
CH
3
(d) 
CH
3
COOH
6. Arrange the following dienes in order of increasing readinity in Diels-Alder reaction
(A) (B) 
NC
(C) 
H
3
C
(D) 
H
3
CO
(a) C < B < A < D (b) B < D < A < C (c) B < A < C < D (d) B < A < D < C
7. Major product obtained in the reaction
H
3
CO
NH
2
 + 
CH
3
 
P ? ? ?
(a) 
NH
2
H
3
CO CH
3
 (b) 
NH
2
H
3
CO
CH
3
(c) 
NH
2
H
3
CO
CH
3
 (d) None of these
8. In the reaction P and Q are:
O
H
D
(a) 
OH
D
 and 
OH
D
Page 3


ASF
1
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
Single Correct Type
1. Arrange the following in order of increasing rate in Diels-Alder reaction.
(A) (B) 
O
(C) 
O
(D) 
N
(a) A < B < D < C (b) B < C < D < A (c) B < A < C < D (d) B < A < D < C
2.
SO
2
H
3
C
 
methyl
Vinyl ketone
A B
?
? ? ? ? ? ? ? ?
Product B in the above reaction is
(a) 
C
O
CH
3
H
3
C
(b) 
H
3
C
C
H
2
C CH
3
O
(c) 
H
3
C
H
2
C C CH
3
O
(d) 
H
3
C
C CH
3
O
(e) 
C
O
CH
3
H
3
C
3. Major product ‘P’ formed in the reaction given below:
Cl
Br
H
3
C
 
NaI acrylo nitrile conc. HCl
dryether
P ? ? ? ? ? ? ? ? ? ? ? ? ? ?
(a) 
C
H
3
C
NH
2
O
 (b) 
C
H
3
C
NH
2
O
 (c) 
C
H
3
C
OH
O
 (d) 
C
H
3
C
NH
2
O
Daily Assignment Organic Chemistry         IIT-JAM 2015
PERICYCLIC REACTIONS
Ashoka Scienific Forum
Developing Scientific Temper Among Students
IIT-JAM | TIFR | DU | BHU | JNU | ISM | PU & All Other University M.Sc. Entrance Exam
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2
ASF
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
4. Product obtained by sigmatropic shift in the given compound is
C
5
H
11
 
sigmatropic shift
?
? ? ? ? ? ?
(a) 
C
5
H
11
(b) 
C
4
H
9
(c) 
C
4
H
9
(d) 
C
5
H
11
5.
O
O
 + 
C
COOCH
3
C
CH
3
 3
H O
A B C
?
? ?
?? ? ?? ? ?? ? ?
Product ‘C’ determined by above series of reactions
(a) 
CH
3
(b) 
COOH
CH
3
(c) 
COOH
COOH
CH
3
(d) 
CH
3
COOH
6. Arrange the following dienes in order of increasing readinity in Diels-Alder reaction
(A) (B) 
NC
(C) 
H
3
C
(D) 
H
3
CO
(a) C < B < A < D (b) B < D < A < C (c) B < A < C < D (d) B < A < D < C
7. Major product obtained in the reaction
H
3
CO
NH
2
 + 
CH
3
 
P ? ? ?
(a) 
NH
2
H
3
CO CH
3
 (b) 
NH
2
H
3
CO
CH
3
(c) 
NH
2
H
3
CO
CH
3
 (d) None of these
8. In the reaction P and Q are:
O
H
D
(a) 
OH
D
 and 
OH
D
ASF
3
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
(b) 
OH
D
 and 
OH
D
(c) 
OH
D
 and 
OH
D
(d) 
OH
D
 and 
OH
D
9. Treatment of 
N
2
COO
 with trans, trans-2,4-hexadiene gives:
(a) 
CH
3
CH
3
(b) 
CH
3
CH
3
 (c) 
CH
3
CH
3
(d) 
CH
3
CH
3
10. The compound given below undergoes electrocyclic reaction to give A on heating, which further undergo
electrocyclic reaction to give B. A and B are:
(a) A ? 
H
R
R
H
 ;  B ? 
R
R
(b) A ? 
R
R
 ;  B ? 
R
R
H
H
(c) A ? 
H
R
R
H
 ;  B ? 
R
R
(d) A ? 
R
R
 ;  B ? 
H
R
R
H
11.
MeO
MeO OMe
 + 
CH
C
COOMe
 
3
H O
A B
?
?
?
? ? ? ? ? ? ?
Product B is
Page 4


ASF
1
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
Single Correct Type
1. Arrange the following in order of increasing rate in Diels-Alder reaction.
(A) (B) 
O
(C) 
O
(D) 
N
(a) A < B < D < C (b) B < C < D < A (c) B < A < C < D (d) B < A < D < C
2.
SO
2
H
3
C
 
methyl
Vinyl ketone
A B
?
? ? ? ? ? ? ? ?
Product B in the above reaction is
(a) 
C
O
CH
3
H
3
C
(b) 
H
3
C
C
H
2
C CH
3
O
(c) 
H
3
C
H
2
C C CH
3
O
(d) 
H
3
C
C CH
3
O
(e) 
C
O
CH
3
H
3
C
3. Major product ‘P’ formed in the reaction given below:
Cl
Br
H
3
C
 
NaI acrylo nitrile conc. HCl
dryether
P ? ? ? ? ? ? ? ? ? ? ? ? ? ?
(a) 
C
H
3
C
NH
2
O
 (b) 
C
H
3
C
NH
2
O
 (c) 
C
H
3
C
OH
O
 (d) 
C
H
3
C
NH
2
O
Daily Assignment Organic Chemistry         IIT-JAM 2015
PERICYCLIC REACTIONS
Ashoka Scienific Forum
Developing Scientific Temper Among Students
IIT-JAM | TIFR | DU | BHU | JNU | ISM | PU & All Other University M.Sc. Entrance Exam
CSIR-NET | GATE | TIFR
2
ASF
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
4. Product obtained by sigmatropic shift in the given compound is
C
5
H
11
 
sigmatropic shift
?
? ? ? ? ? ?
(a) 
C
5
H
11
(b) 
C
4
H
9
(c) 
C
4
H
9
(d) 
C
5
H
11
5.
O
O
 + 
C
COOCH
3
C
CH
3
 3
H O
A B C
?
? ?
?? ? ?? ? ?? ? ?
Product ‘C’ determined by above series of reactions
(a) 
CH
3
(b) 
COOH
CH
3
(c) 
COOH
COOH
CH
3
(d) 
CH
3
COOH
6. Arrange the following dienes in order of increasing readinity in Diels-Alder reaction
(A) (B) 
NC
(C) 
H
3
C
(D) 
H
3
CO
(a) C < B < A < D (b) B < D < A < C (c) B < A < C < D (d) B < A < D < C
7. Major product obtained in the reaction
H
3
CO
NH
2
 + 
CH
3
 
P ? ? ?
(a) 
NH
2
H
3
CO CH
3
 (b) 
NH
2
H
3
CO
CH
3
(c) 
NH
2
H
3
CO
CH
3
 (d) None of these
8. In the reaction P and Q are:
O
H
D
(a) 
OH
D
 and 
OH
D
ASF
3
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
(b) 
OH
D
 and 
OH
D
(c) 
OH
D
 and 
OH
D
(d) 
OH
D
 and 
OH
D
9. Treatment of 
N
2
COO
 with trans, trans-2,4-hexadiene gives:
(a) 
CH
3
CH
3
(b) 
CH
3
CH
3
 (c) 
CH
3
CH
3
(d) 
CH
3
CH
3
10. The compound given below undergoes electrocyclic reaction to give A on heating, which further undergo
electrocyclic reaction to give B. A and B are:
(a) A ? 
H
R
R
H
 ;  B ? 
R
R
(b) A ? 
R
R
 ;  B ? 
R
R
H
H
(c) A ? 
H
R
R
H
 ;  B ? 
R
R
(d) A ? 
R
R
 ;  B ? 
H
R
R
H
11.
MeO
MeO OMe
 + 
CH
C
COOMe
 
3
H O
A B
?
?
?
? ? ? ? ? ? ?
Product B is
4
ASF
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
(a) 
OH
COOH
OH
(b) 
OH
COOH
HO
 (c) 
OH
COOH
OH
 (d) 
OH
COOH
HOOC
12. Heating of 
CH
3
CD
2
 gives
(a) 
CHD
CH
2
D
(b) 
CD
2
CH
3
(c) 
CH
2
CHD
2
(d) None of these
13. cis,cis,cis-cyclooct-1,3,5-triene
?
P(C
8
H
10
)
P is
(a) 
H
H
(b) 
H
H
(c) 
H
H
(d) 
H
H
14. ‘P’ obtained in above reaction is treated with
to
3 3 14 16 4 give
H COOCC CCOOCH Q (C H O ) ? ? ? ?
(a) 
COOCH
3
COOCH
3
(b) 
COOCH
3
COOCH
3
(c) 
COOCH
3
COOCH
3
(d) 
COOCH
3
COOCH
3
15.
heated
to give
Q ? ? ? ? cyclobutene + R
R is
(a) 
COOCH
3
COOCH
3
(b) 
COOCH
3
COOCH
3
(c) 
COOCH
3
COOCH
3
(d) 
COOCH
3
COOCH
3
Page 5


ASF
1
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
Single Correct Type
1. Arrange the following in order of increasing rate in Diels-Alder reaction.
(A) (B) 
O
(C) 
O
(D) 
N
(a) A < B < D < C (b) B < C < D < A (c) B < A < C < D (d) B < A < D < C
2.
SO
2
H
3
C
 
methyl
Vinyl ketone
A B
?
? ? ? ? ? ? ? ?
Product B in the above reaction is
(a) 
C
O
CH
3
H
3
C
(b) 
H
3
C
C
H
2
C CH
3
O
(c) 
H
3
C
H
2
C C CH
3
O
(d) 
H
3
C
C CH
3
O
(e) 
C
O
CH
3
H
3
C
3. Major product ‘P’ formed in the reaction given below:
Cl
Br
H
3
C
 
NaI acrylo nitrile conc. HCl
dryether
P ? ? ? ? ? ? ? ? ? ? ? ? ? ?
(a) 
C
H
3
C
NH
2
O
 (b) 
C
H
3
C
NH
2
O
 (c) 
C
H
3
C
OH
O
 (d) 
C
H
3
C
NH
2
O
Daily Assignment Organic Chemistry         IIT-JAM 2015
PERICYCLIC REACTIONS
Ashoka Scienific Forum
Developing Scientific Temper Among Students
IIT-JAM | TIFR | DU | BHU | JNU | ISM | PU & All Other University M.Sc. Entrance Exam
CSIR-NET | GATE | TIFR
2
ASF
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
4. Product obtained by sigmatropic shift in the given compound is
C
5
H
11
 
sigmatropic shift
?
? ? ? ? ? ?
(a) 
C
5
H
11
(b) 
C
4
H
9
(c) 
C
4
H
9
(d) 
C
5
H
11
5.
O
O
 + 
C
COOCH
3
C
CH
3
 3
H O
A B C
?
? ?
?? ? ?? ? ?? ? ?
Product ‘C’ determined by above series of reactions
(a) 
CH
3
(b) 
COOH
CH
3
(c) 
COOH
COOH
CH
3
(d) 
CH
3
COOH
6. Arrange the following dienes in order of increasing readinity in Diels-Alder reaction
(A) (B) 
NC
(C) 
H
3
C
(D) 
H
3
CO
(a) C < B < A < D (b) B < D < A < C (c) B < A < C < D (d) B < A < D < C
7. Major product obtained in the reaction
H
3
CO
NH
2
 + 
CH
3
 
P ? ? ?
(a) 
NH
2
H
3
CO CH
3
 (b) 
NH
2
H
3
CO
CH
3
(c) 
NH
2
H
3
CO
CH
3
 (d) None of these
8. In the reaction P and Q are:
O
H
D
(a) 
OH
D
 and 
OH
D
ASF
3
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
(b) 
OH
D
 and 
OH
D
(c) 
OH
D
 and 
OH
D
(d) 
OH
D
 and 
OH
D
9. Treatment of 
N
2
COO
 with trans, trans-2,4-hexadiene gives:
(a) 
CH
3
CH
3
(b) 
CH
3
CH
3
 (c) 
CH
3
CH
3
(d) 
CH
3
CH
3
10. The compound given below undergoes electrocyclic reaction to give A on heating, which further undergo
electrocyclic reaction to give B. A and B are:
(a) A ? 
H
R
R
H
 ;  B ? 
R
R
(b) A ? 
R
R
 ;  B ? 
R
R
H
H
(c) A ? 
H
R
R
H
 ;  B ? 
R
R
(d) A ? 
R
R
 ;  B ? 
H
R
R
H
11.
MeO
MeO OMe
 + 
CH
C
COOMe
 
3
H O
A B
?
?
?
? ? ? ? ? ? ?
Product B is
4
ASF
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
(a) 
OH
COOH
OH
(b) 
OH
COOH
HO
 (c) 
OH
COOH
OH
 (d) 
OH
COOH
HOOC
12. Heating of 
CH
3
CD
2
 gives
(a) 
CHD
CH
2
D
(b) 
CD
2
CH
3
(c) 
CH
2
CHD
2
(d) None of these
13. cis,cis,cis-cyclooct-1,3,5-triene
?
P(C
8
H
10
)
P is
(a) 
H
H
(b) 
H
H
(c) 
H
H
(d) 
H
H
14. ‘P’ obtained in above reaction is treated with
to
3 3 14 16 4 give
H COOCC CCOOCH Q (C H O ) ? ? ? ?
(a) 
COOCH
3
COOCH
3
(b) 
COOCH
3
COOCH
3
(c) 
COOCH
3
COOCH
3
(d) 
COOCH
3
COOCH
3
15.
heated
to give
Q ? ? ? ? cyclobutene + R
R is
(a) 
COOCH
3
COOCH
3
(b) 
COOCH
3
COOCH
3
(c) 
COOCH
3
COOCH
3
(d) 
COOCH
3
COOCH
3
ASF
5
2637, Hudson Lane, Behind Khalsa College, Near G .T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi - 110009
Mob. 09555785548, 08860929430, e-mail: info@asfinstitute.com, www .asfinstitute.com
16.
CH
3
CH
3
H
3
C
H
3
C
 is heated at 176ºC to give A. A is
(a) 
H
H
CH
3
H
3
C
H
3
C
CH
3
(b) CH
3
H
CH
3
H
(c) CH
3
H
CH
3
H
3
C
H
3
C
H
(d) 
H
H
CH
3
CH
3
17. Arrange 
(A)
benzene
, 
(B)
triphene
, 
(C)
Pyrrole
 
(D)
furane
In increasing order of rate in Diels-Alder reaction
(a) A (b) B (c) C (d) D
18. The product of the thermal rearangement is
O
  
6 6
TF, C H
?
? ? ? ? ?
(a) 
O
(b) 
O
 (c) 
O
 (d) 
O
19. Give the product expected from heating the following compound
H H
(a) 
H H
(b) 
H H
(c) 
H H
(d) 
H H
20. Match the column I with column II
Column I Column II
(A) +   (1) 4 + 4
(B) +   (2) 2 + 2
(C)  +   (3) 4 + 2
(D)
OC
O
OC
  
OC
O
OC
(4) 2 + 2 + 2
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