09

A3
CE
7

0
58

91
Paper / Subject Code: 92879 / Chemistry : Paper II - Organic Chemistry: Synthetic Organic Chemistry - II. (R-2019)

29
04
99
3A

79

A3
CE
10

0
58
15

29
04
99

99
3A
20

A3
CE
87

10
F1

15

04
99

9
A
AD

CE
12

87
3

0
5

91
BF

A5
Time: 2:30 Hours Marks: 60

99
AD

20

79
47

53

0
1

58

C
91
F
90

DF

01

9
B
1. A. Attempt any two of the following:

A
8

79

9
32

47

12

53

10
A

58
i) Suggest the synthesis of the following using the protection-deprotection

4A

F
90

01

99
B

A
AD
2
E0

47

12

87
protocol.

3
3

15
4A

F
90

DF

A5
9C

7B

20
32
0
09

3
A
E

04

F1

58
15
A

BF
9C
91

29

A
AD
4

0
E0

47
79

12
9

53
A3
0

BF
90
58

F
9C
1

01
D
4
99

2
3A

E0

47

12
09

A
A3
87

BF
90

DF
C
15

91
A5

04
9

2
20

47
79

FA
3
CE

F1
3

4A
F1

90
58
5

7B

AD
1

99

32
A
AD

E0
20

79

04
3

10

4A

BF
F1

58

C
5
BF

29
01

9
3A
AD

E0

47
79

3
47

12

10

4A

90
58

9C
15
BF
90

99

32
A
D

E0
20

09
32

47

87
3
A

ii) Explain the term Functional Group Interconversions (FGI) and Functional

4A
F1

9C
5

91
4A

F
90

A5
1
7B

AD

E0
20

79
Group Additions (FGA) with suitable examples.

09
32
E0

53
04

F1

58

9C
91
4A

BF

iii) Provide a retro-synthesis of the following compounds.

9C

1
9

A
D

20

79

09
32
E0

47
09

53
A

F1

58

91
4A

F
90
9C
91

01
7B

3A
D

79
2
E0
79

12
09

FA
3

58
15
A

90
58

DF
9C
91

7B

3A
04

20
32
3A

79

09

A
CE

04

F1

15
4A

F
58
15

91

7B
9

AD

20
9

2
3A

E0
20

79

09

A3

04

F1
BF
1

9C
15

91
DF

29
A5

AD
04

iv) What are acyl anion equivalent? Discuss with the conversion of
20

47
79

3
CE
53

0
FA

BF
F1

90
58

formaldehyde to acetaldehyde.
1

04
01

99

99
7B

2
3A
AD

47

B Attempt any one of the following:

3

4
CE
12

87

4A
04

90
5

91
F

DF

5
01

i) Complete the following reaction sequence by identifying A-D.

99
7B

32
3A

E0
79
12

10
FA

4A
04

58

9C
5
DF

01

99
B
29

3A

E0
09
47

12

87
FA
A3

9C
5

1
0

DF

A5
01

99
B
29
04

09
47

12

87
3
FA
A3
CE

15

91
0

DF

A5
B
29
04

ii) Give the equation for the protection and deprotection of

20

79
47

53
FA
A3
E

F1

58

-OH group as MOM ether and -NH2 as Benzyloxy carbonyl (CBz)

0
9C

01
B
29

3A
D
04

47

12
9

2. A Attempt any two of the following:

A

8
A3
E
10

15
BF
0

DF
9C

29
04
99

20

i) An important guideline in retrosynthetic analysis is to use the symmetry

47
9

FA
A3
E
87

F1
10

0
9C

of the target molecule. On the basis of this guideline identify the best
7B
29

AD
04
9
79

A3
E

04

points of disconnection in the following molecule. Show the complete

10

BF
8

9C

29
A5

04
9

retrosynthetic pathway and the synthetic sequence.

47
79

3
E
3

10

4A

90
8

9C
15

A5

32
E0
0

79

9
12

10

4A
8

9C
15

A5

E0
20

79

9
3

10
F1

9C
15

A5

9
AD

20

79

09
3
F1

32582 Page 1 of 5
15

91
BF

A5
AD

79
47

12

8
15
BF

DF

A5
20
47

3
FA

47BFADF120153A587991099CE04A3290
F1

15
 47 12 87 CE 04
BF 0 15 99 04 7B
AD 3 10 A3 FA
A5 9 9C 29 DF
47 F1
20 8 79 E 04 1
BF 15 9 04 7B 20
AD 3 A5
10
9
A3 FAD 15
3A
9C 29
F1
20 8 79 E 047 F1 58
FA 15 9 04 B 20 79
3 10 A3 FA 15 91
DF A5 9 9C 29 DF 3A 09
8 0 9C

32582
E

B
12 79 47 12 58
0 15 9 04 B 01 79 E0
3 10 A3 FA 53 91 4A
9

i)
iv
09
ii)

A5 29 32

iii)
F1 8 9C 0 DF A5 9C
20 79 E 47 12 8 79
90
47
15 9 04 B 01 91
E0
3 A5
10
9
A3
29
FA 5 3A 09
4A
32
BF
AD
8 9C 0 DF 9C
79 E 47 12 58
79
90
47 F1
15 9 04 B 01 20 91
E0
3 A5
10
9
A3
29
FA 53A 15 09
4A
32
BF
AD
8 9C DF 0 9 5 9 3A
79 E0 47 12 87 CE 04 58 F1
91 4A BF 01 99 04 7B 20 79
09 3 A 5 1 0 A 3 F A 1 5 91

A, B, C and D.
9C 29 D 3A 9 9C 2 D 3 09
E0 04
7B
F1
20
58
79 E0
90
47 F 12
A5
87 9C
4A FA 15 91 4A BF 01 99 E0
32 3 0 32 AD 5 3 1 0
4A
90 DF A5
87
99
CE 90 F1 A58 9 9C 32
90
47 12
99 4 20 79 E 47
BF 01
53 10
04 7B
F 15 91 04A BF
AD 99
A3
2 A D 3A 09 3
F1 A5 9 9C 2 AD
synthesis from cyclopentadiene.

87 CE 04 F1 58 90

and the corresponding synthesis.

20 F1

Attempt any one of the following:

99 04 7B 20 79 E0 47 20
15 1 A 3 FA 1 5 9 1 4 A B F 15
3 0

Page 2 of 5
3A 09
58 9C 29 D A 9 9 32 AD 3A
79 E0 04 F1 58 C 90 F 58
91 4A 7B
F
20
1
79
9
E0
4
47
B
12
0 7
09
9C 3 2 A DF
53
A5
10
99
A3 F A 15
3A
90 29

47BFADF120153A587991099CE04A3290
CE DF 58
E0
4A
47
BF
12
01
87
99 04
04
7B 1 20 79
F 1
its synthesis, as per the pathway suggested by you.

32 AD 53 10 A3 5 91
90 A 9 9 2 AD 3A 09
47 F1
20
58
79 C E0
90
47 F 12 587
BF 15 91 4A BF 01 99
AD 3A 09
9C 3 2 A DF
53
A5
10
99
F1 58 90 CE
20 79 E0 47 12 87
15 91 4A BF 01 99
3A 09 32 AD 53 10
9C A 99
cyclopentadiene is one of the starting materials. Using this, write its

58 90 F1 58 CE
Propose a retrosynthetic analysis for the following molecule such that

79 E0 47
reaction. With this information, write a suitable retrosynthetic analysis

91 4A BF 20 79 04
15 91
The synthesis of the following molecule involves a Robinson annulation

Complete the following retrosynthetic analysis by drawing structures for

3 A
For the following molecule, suggest a retrosynthetic pathway. Also write

09 29 D 3A 0 9
A3
9C
E0 04 F 12 58 9 CE
4

4A 7B 0 79 04
FA 15 91
32
90 DF 3 A5 0 99
A3
29
47 12 87 CE 0
BF 01 99 04
AD 53 10 A3
A 9 9 29
F1 58 C 0
Paper / Subject Code: 92879 / Chemistry : Paper II - Organic Chemistry: Synthetic Organic Chemistry - II. (R-2019)
 09

A3
CE
7

0
58

91
Paper / Subject Code: 92879 / Chemistry : Paper II - Organic Chemistry: Synthetic Organic Chemistry - II. (R-2019)

29
04
99
3A

79

A3
CE
10

0
58
15

29
04
99

99
3A
20

A3
CE
87

10
ii) Complete the following retrosynthetic pathway by drawing structures for

F1

15

04
99

9
A, B, C and D.

A
AD

CE
12

87
3

0
5

91
BF

A5
1

99
AD

20

79
47

53

0
1

58

C
91
F
90

DF

01

9
B

79

9
32

47

12

53

10
A

58
4A

F
90

01

99
B

A
AD
2
E0

47

12

87
3
3

15
4A

F
90

DF

A5
9C

7B

20
32
0
09

3
A
E

04

F1

58
15
A

BF
9C
91

29

A
AD
4

0
E0

47
79

12
9

53
A3
0

BF
90
58

F
9C
1

01
D
4
99

2
3A

E0

47

12
09

A
A3
87

BF
90

DF
C
15

91
A5

04
9

2
20

47
79

FA
3
CE

F1
3

4A
F1

90
58
5

7B

AD
1

99

32
A
AD

E0
20

79

04
3

10

4A

BF
F1

58

C
5
BF

29
01

9
3. A Attempt any two of the following: 8

9
3A
AD

E0

47
79

3
47

12

10

4A
i) Give product and mechanism of following reaction.

90
58

9C
15
BF
90

99

32
A
D

E0
20

09
32

47

87
3
A

4A
F1

9C
5

91
4A

F
90

A5
1
7B

AD

E0
20

79

09
32
E0

53
04

F1

58

9C
91
4A

BF
9C

1
9

A
D

20

79

09
32
E0

47
09

53
A

F1

58

91
4A

F
90
9C
91

01
7B

3A
D

79
ii) Give a brief account of applications of cryptands in organic synthesis.
2
E0
79

12
09

FA
3

58
15
A

iii) Give the applications of Sc(OTf)3 as a water tolerant Lewis acid catalyst
90
58

DF
9C
91

7B

3A
04

20
32
3A

79

in the following reactions:

09

A
CE

04

F1

15
4A

F
58
15

91

Diels Alder reaction

7B
9

AD

20
9

2
3A

E0
20

79

09

Michael reaction
A3

04

F1
BF
1

9C
15

91
DF

29
A5

Aldol condensation
AD
04
20

47
79

3
CE
53

Friedel Crafts reaction

FA

BF
F1

90
58

04
01

99

99

iv) What is Kolbe's reaction? Discuss the mechanism involved. Give one
7B

2
3A
AD

47
3
CE
12

87

4A

application.
04

90
5

91
F

DF

5
01

99
7B

32
3A

E0
79

B Attempt any one of the following: 4

12

10
FA

4A
04

58

9C
5

i) What are cyclodextrins? Discuss the structure and two applications of

DF

01

99
B
29

3A

E0
09
47

cyclodextrins.
12

87
FA
A3

9C
5

1
0

DF

A5
01

99

ii) Give product, name and mechanism of following reaction.

B
29
04

09
47

12

87
3
FA
A3
CE

15

91
0

DF

A5
B
29
04

20

79
47

53
FA
A3
E

F1

58
0
9C

01

4. A Attempt any two of the following:

B

8
29

3A
D
04

47

12
9

A
A3
E
10

15

i) Explain the terms reductive elimination and 18-electron rule with suitable
BF
0

DF
9C

29
04
99

20

examples.
47
9

FA
A3
E
87

F1
10

ii) Complete the following reaction and give the mechanism of the same.
0
9C

7B
29

AD
04
9
79

A3
E

04
10

BF
8

9C

29
A5

04
9

47
79

3
E
3

10

4A

90
8

9C
15

A5

32
E0
0

79

9
12

10

4A
8

9C
15

A5

E0
20

79

9
3

10
F1

9C
15

A5

9
AD

20

79

09
3
F1

32582 Page 3 of 5
15

91
BF

A5
AD

79
47

12

8
15
BF

DF

A5
20
47

3
FA

47BFADF120153A587991099CE04A3290
F1

15
 47 12 87 CE 04
BF 0 15 99 04 7B
AD 3 10 A3 FA
A5 9 9C 29 DF
47 F1
20 8 79 E 04 1
BF 15 9 04 7B 20
AD 3 A5
10
9
A3 F AD 15
3A
9C 29
F1
20 8 79 E 0 47 F1 58
15 9 04 B 20 79

5.
FA 3 10 A3 FA 15 91
DF A5 9 9C 29 DF 3A 09
8 0 9C

32582
E

B
12 79 47 12 58
0 15 9 04 B 01 79 E0
3 10 A3 FA 53 91 4A
9

i)
09

ii)
A5 29 32

(c)
(a)
iv)

(b)
iii)

F1 8 9C 0 DF A5 9C
20 79 E 47 12 8 79
90
47
15 9 04 B 01 91
E0
3 A5
10
9
A3
29
FA 5 3A 09
4A
32
BF
AD
8 9C 0 DF 9C
79 E 47 12 58
79
90
47 F1
15 9 04 B 20 01 91
E0
3 A5
10
9
A3
29
FA 15 5 3A 09
4A
32
BF
AD
8 9C DF 9 0 9 3A 5
79 E0 47 12 87 CE 04 58 F1
91 4A BF 01 99 04 7B 20 79
09 3 A 5 1 0 A 3 F A 1 5 91
9C 29 D 3A 9 9C 2 D 3 09
E0 04
7B
F1
20
58
79 E0
90
47 F 12
A5
87 9C
4A FA 15 91 4A BF 01 99 E0
32 3 0 5 1 4A

How will you convert?

90 DF A5 99 32
90
AD 3 A 0 9 32
47 12 87 CE 4 F1 58 9C 90
BF 01 99 04 7B 20 79 E 0 47
AD 53 10 A3 F A 15 91 4A BF
99 2 D 3A 09 3

analysis of phenyl cyclohexane

F1 A5
87 CE 9 04 F1 58 9C 2 90
AD
20 F1

Attempt any one of the following:

99 20 79 47

Answer any four of the following:

04 7B E0 20
15 1 A 3 FA 1 5 9 1 4 A B F 15
3 0

Page 4 of 5
3A 09
58 9C 29 D A 9 9 32 AD 3A
79 E0 04 F1 58 C 90 F 58
91 4A 7B
F
20
1
79
9
E0
4
47
B
12
0 7
09
9C 3 2 A DF
53
A5
10
99
A3 F A 15
3A
90 29

47BFADF120153A587991099CE04A3290
CE DF 58
E0
4A
47
BF
12
01
87
99 04
04
7B 1 20 79
32 AD 53 10 A3 F 1 5 91
90 A 9 9 2 AD 3A 09
47 F1
20
58
79 C E0
90
47 F 12 587
BF
compounds, alkyl halides and α-functionalized carbonyls.
15 91 4A BF 01 99
AD 3A 09
9C 3 2 A 53 10
99
Give name, product and mechanism of the following reaction

F1 58 90 DF A5
20 79 E0 47 12 87 CE
Complete the following reactions by identifying A, B, C and D.

Explain the term Convergent synthesis using suitable examples.

15 91 4A BF 01 99
Give the product, name and mechanism of the following reaction.

Using functional group addition as one of the steps, write the retro
3A 09 32 AD 53 10
58 9C 90 F1 A 58 99
79 E0 47 20 79 CE
91 4A BF 15 91 04
3 A
What is the action of SmI2 on the following compounds - aldehydes, nitro

09 29 D 3A 0 9
A3
9C
E0 04 F 12 58 9 CE
4

7B 0 79

12
4A FA 15 91 04
32
90 DF 3 A5 0 99
A3
29
47 12 87 CE 0
BF 01 99 04
AD 53 10 A3
A 9 9 29
F1 58 C 0
Paper / Subject Code: 92879 / Chemistry : Paper II - Organic Chemistry: Synthetic Organic Chemistry - II. (R-2019)
 47 12 87 CE 04
BF 0 15 99 04 7B
AD 3 10 A3 FA
A5 9 9C 29 DF
47 F1
20 8 79 E 04 1
BF 15 9 04 7B 20
AD 3 A5
10
9
A3 FAD 15
3A
9C 29
F1
20 8 79 E 047 F1 58
FA 15 9 04 B 20 79
3 10 A3 FA 15 91
DF A5 9 9C 29 DF 3A 09
8 0 9C

32582
12
0 79 E 47 12 58
79
15 9 10
04 B 01 91
E0
4A
3 9
A3 FA 53 09

(f)
A5 29 32
(e)

(h)
(g)
(d)

F1 8 9C 0 DF A5 9C
20 79 E 47 12 8 79
90
47
15 9 04 B 01 91
E0
3 A5
10
9
A3
29
FA 5 3A 09
4A
32
BF
AD
8 9C 0 DF 9C
79 E 47 12 58
79
90
47 F1
15 9 04 B 01 91
E0 20
3 A5
10
9
A3
29
FA 53A 09 15 4A
32
BF
AD
8 9C DF 0 9 5 9 3A
79 E0 47 12 87 CE 04 58 F1
91 4A BF 01 99 04 7B 20 79
09 3 A 5 1 0 A 3 F A 1 5 91
9C 29 D 3A 9 9C 2 D 3 09
E0 04 F1 58 90 F A5 9C

deprotection agent.
4A 7B 20 79 E0 47 12 87 E0
FA 15 91 4A BF 01 99
32 3 0 32 AD 5 3 1 0
4A
90 DF A5
87
99
CE 90 F1 A58 9 9C 32
90
47 12
99 4 20 79 E 47
BF 01
53 10
04 7B
F 15 91 04A BF
AD 99
A3
2 A D 3A 09 3
F1 A5
87 CE 9 04 F1 58 9C 2 90
AD
20 99 04 7B 20 79 E0 47 F1
15 1 A 1 9 4 B 20
3 FA 5 1 A F

**************
3 0 15

Page 5 of 5
3A 09
58 9C 29 D A 9 9 32 AD 3A
79 E0 04 F1 58 C 90 F 58
91 4A 7B
F
20
1
79
9
E0
4
47
B
12
0 7
09
9C 3 2 A DF
53
A5
10
99
A3 F A 15
3A
90 29

47BFADF120153A587991099CE04A3290
CE DF 58
E0
4A
47
BF
12
01
87
99 04
04
7B 1 20 79
32 AD 53 10 A3 F 1 5 91
A 9 3
Discuss with examples cathodic reduction of olefins.

90 9C 2 AD A 09
47 F1
20
58
79 E0
90
47 F 12 587
Complete the following reaction and give its mechanism.

BF 15 91 4A BF 01 99
AD 3A 09
9C 3 2 A DF
53
A5
10
99
F1 58 90 CE
20 79 E0 47 12 87
How will you synthesise the following molecule from acetylene?

15 91 4A BF 01 99
3A 09 32 AD 53 10
9C A 99
Give the applications of Ce(IV) in i) synthesis of quinoxaline ii) as a

58 90 F1 58 CE
79 E0 47 20 79
91 4A BF 15 91 04
What are micelles? Write two applications of micelle catalysed reactions.

09 3 29 A D 3A 0 9
A3
9C
E0 04 F 12 58 9 CE
4A 7B 0 79 04
FA 15 91
32
90 DF 3 A5 0 99
A3
29
47 12 87 CE 0
BF 01 99 04
AD 53 10 A3
A 9 9 29
F1 58 C 0
Paper / Subject Code: 92879 / Chemistry : Paper II - Organic Chemistry: Synthetic Organic Chemistry - II. (R-2019)