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PART-A
Q.1 to Q.05: Carry 1 Mark each.
1. The major product (P) formed in the following reaction
O
NaOH
Me Me (P)
EtOH
O
O O
Me
(a) (b)
Me
Me
O
Me
(c) Me (d) Me Me
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O O O O
O
OH
CN
O OH
(a) (b)
OH Cl O Cl
CN CN
(c) (d)
O Cl Cl
CN CN
4. The major product (P) formed in the following reaction,
O
(i) m-CPBA
(P)
(ii) LiAlH4
OH
HO OH
CHCl3, KOH
(P)
Bu4NHSO4, H2O
N
H
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33
Cl
Cl
(a) (b)
N N
CH2 Cl
(c) (d)
N N
H H
Cl
Q.6 to Q.10: Carry 2 Marks each.
6. The major product (P) formed in the following reaction
O
O
(a) (b)
BPSO BPSO
H H
O
CHO
CH3
(c) (d)
BPSO
BPSO
H
H
7. The major product (P) formed in the following reaction
O
CO2Me
(i) Br2/Et2O (2 eq.)
(P)
(ii) NaOMe/MeOH
O
CO2Me MeO2C CO2Me MeO2C CO2Me
Br CO2Me
CO2Me
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North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
44
8. The major product (P) formed in the following reaction
(i) SOCl2
(ii) NaN3/H2O
(P)
(iii) heat
(iv) H2O/H+
C
O OH
Cl
(a) (b) (c) (d)
H OH
NH2 N
H
N NH
RO RO
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
55
Br
Br
(a) (b)
Br
(c) (d)
Br
PART-B
O
Me Me
COOMe
COOMe
NaH, Toluene
(b)
COOMe
Me Me Me Me
Bn Bn
CN
OH DEAD/ Ph3P O
(d)
THF
COOH
O
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North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
66
12. Correct statement(s) in the following is/are
(a) In Pinacol-Pinacolone rearrangement, migratory aptitude order is
NH2 COOH CH3 NO2
LDA
(a)
NNHTs
Me Me
CO2Me
Na, NH3 OH
(b) alcohol
CO2H COOH
COOEt
COOEt
NaOEt
+ EtOOC–COOEt O
Toluene, Et2O COOEt
(c) COOEt
COOEt
O COOEt
O
(d) ClCH2–COOEt
KOtBu, tBuOH
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77
PART-C
Q.16 to Q.17: Carry 1 Mark each.
16. Carbene intermediate formed in the following reaction
(1) Reimer Tiemann reaction (2) Simmons smith reaction
(3) Wolff rearrangement (4) Wagner Meerwein rearrangement
(5) Wittig reaction (6) Corey fuchs reaction
17. Number of radical initiated reactions in the following is ____________
(1) Cannizzaro reaction (2) Clemmension reduction reaction
(3) Acyloin condensation (4) Mc-murry reaction
(5) Birch reduction (6) Perkin reaction
Q.18 to Q.21: Carry 2 Marks each.
18. Number of product(s) formed in the following reaction,
O O
TiCl3, Zn
+
H3C C2H5 Ph H
19. Number of aldol product(s) formed in the following reaction,
CH3
20. Number of reactions/rearrangements in the following in which Isocyanate intermediate formed ________
(1) Hofmann rearrangement (2) Curtius rearrangement
(3) Lossen rearrangement (4) Schmidt rearrangement
(5) Baeyer villigers oxidation (6) Beckmann rearrangement
(7) Bamford-stevens reaction (8) Chichibabin reaction
21. Carbon-carbon bond formation occur in the following
(1) Perkin condensation
(2) Benzoin condensation
(3) Clemmension reduction
(4) Cannizzaro reaction
(5) Stobbe condensation
(6) Claisen ester condensation
(7) Mc-Murry reaction
(8) Baeyer villigers oxidation
(9) Fries rearrangement
(10) Reimer-Tiemann Reaction
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
88
PART - A
1. (b) 2. (c) 3. (b) 4. (d) 5. (b) 6. (b) 7. (b)
8. (a) 9. (c) 10. (a)
PART - B
11. (a,b,c,d) 12. (b,c) 13. (a,c) 14. (a,c,d) 15. (a,b,c,d)
PART - C
16. (2) 17. (4) 18. (6) 19. (4) 20. (4) 21. (7)
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455