ORGANIC CHEMISTRY
Assignment
Reagents
2 1. NaNH (excess)
2 4 1. H / Pd / BaSO
1. H C C H
2. H CO (2eq)
A
B
2 2. O H
3. mCPBA
What is the major product B and what selectivity involves from product A to B
OH
O O
(a) and stereoselectivity (b) O and stereoselectivity
O O
OH
(+)
–
H
O
(c) O and stereoselectivity (d) None of these
O
H
2.
Br
CHEM ACADEMY
1. Mg / Et 2O(dy)
O
1. PCC / CH 2Cl2
A
2. Ph CH CH MgBr2
B
2
|| 3. H3O
2. CH3 C H
3. H3O
What is the major product B
OH O OH
O
(a) Ph (b) Ph (c) Ph (d) Ph
Me Me Me Me
O O 1. EtO Na 1. NaNH2
3. A
2. Me I
B
2.
OMe Br 3. H3O
3. OH OH H 3O /
What is structure of major product B
O
O
(a) (b)
Me Me
O
O
(c) Me (d) OH
Me
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1. Mg / dry ether 1. PBr3 MeOH / H
A B C
4. 2. EtCHO 2. Mg / dry ether
Br 3. CO2
What is the major product C
CH2OH
(a) (b) (c) O (d) O
EtOOC HOOC MeO C MeO C
O
1. Me CuLi / 0ºC
2
A
O Me
5. 2.
H
What is the major product A and its mechanism
O H2 OH O H2 OH O H2 OH O H2 OH
C C H C C H C C H C C H
Me Me Me Me
(a) Me (b) Me (c) Me (d) Me
(SN2) (SN2) (SN2) (SN2)
6.
O
CHEM ACADEMY
1. PhMgBr / dry ether
2. H PO
2
A
3 4
B
H / Pd / C
What is major product B
Ph Ph
(a) (b) (c) (d) None of these
HO
CN
1. NaOH(excess) 1. LiAlH 4
A B
7. 2. MeI (2eq.) 2. NaNO / dil. HCl 2
05ºC
HO
What is the major product B
MeO N2 Cl MeO OH
(a) (b)
MeO MeO
Me
HO OH MeO
OH
(c) (d)
MeO MeO
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1. mCPBA
8.
2. NaOH / H O
A
2
Me O
What is major product (A)?
COOH COOH COOH
(a) (b) (c) (d) None of these
OH OH OH
Me Me Me
O
Me
1. PPh 3 CH COOMe H2O
A B
9. 2. mCPBA
3. NaCN / DMF
What is the major product B?
MeOOC CN MeOOC OH HOOC COOH HOOC OH
OH CN COOH
Me Me Me Me
(a) (b) (c) (d)
O
MgBr
CHEM ACADEMY
Me
1.
1. O3 / Me2S / 78ºC
10. A
2. KOH / EtOH
B
2. H3PO 4
What is structure of major product B
O
Ph
(a) O (b) Ph (c) (d) None of these
C Me Ph
Me
O
1.
O NaOH / H2O
11. A B
2. O3/H2O2/–78ºC
O
What is the major product B and it mechanism of formation
HOOC COOH HOOC COOH
(a) and Nu substitution (b) and Nu additon
HOOC COOH HOOC COOH
O O O O
O O
(c) and Nu substitution (d) and Nu addition
HOOC COOH HOOC COOH
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Me
12. mCPBA(1eq)
A
What is the structure of major product A and its selectivity
Me
Me
O
(a) and regio selectivity (b) and regio selectivity
O
Me Me
O O
(c) and chemo selectivity (d) and chemo selectivity
13. 1. H 2 / Pd / C 1. O / Me S / 78ºC
3 2
Heat
A
2. KOH / EtOH
B
CHEM ACADEMY 2. MeLI
3. H 2SO4
What is the major product B O
O O C Me
Me
Me
(a) Me (b) (c) (d)
14. PCC
1. MeLi / Et O
A B
2
2. H3O
What is major oxidizing product B
Me Me Me
OH OH
(a) (b) (c) No reaction (d)
O OH
Br
1. nBuLi / dry ether
3 1. H O
A
2. mCPBA
B
15. 2. CO2 / H
3. NaOH / H 2O
3. MeLi
What is the major product B?
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O O
OH
O C Me C OMe
(a) (b) (c) (d) None of these
NO2 NO2
16. A
NO2 NH2
What is the reagent A used in following conversion
(a) Sn/HCl (b) Fe/HCl
(c) (NH4)2Sx (yellow ammonium sulphide) (d) None of these
ANSWER KEY
1. B 2. A 3. A 4. C 5. B 6. A 7. B
8. A 9. A 10. B 11. A 12. A 13. A 14. A
15. C 16. C
CHEM ACADEMY
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Ph.: 011-41415514, 09136597244, Web.: www.chemacademy.co.in
