NPTEL Chemistry Reagents and Organic reactions

Solutions

Lecture 1
OH
OH CHO
1. HCHO
A B C

MeO2C OH
2.
MeO2C OH

H O H O
HO O
3. NCOPh NCOPh
HO O
H O H O
D E
OH
4. Ph
Ph
OH

OH OH
5. O HO

O OH O G OH
F
TsHN O
6.
Ph OCH3
OH
NHTs
OH
7.

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NPTEL Chemistry Reagents and Organic reactions

Lecture 2
OH

N CO2H
1. 1. 2. 3. 4. CO2Me 5.
OH N CO2H N
OH O
O

OH
6.

2. 1. MnO2, solvent free, RT 2. Mn(III)salen, NaOCl 3. A. KMnO4/aq. NaOH. B. MnO2/CH2Cl2, RT

4. MnO2, benzene/reflux

Lecture 3
O
O OH
O CO2H
1. 1. CH3 CO2H 5.
Me 2. 3. 4. CO2H
O

Lecture 4
O O
OH O O O
1. 2. 3. 4. Ph 5. 6.
CHO

O CH2OH
N
MeO
7. 8. 9. CHO
O
N

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NPTEL Chemistry Reagents and Organic reactions

Lecture 5
O Me
O
O O MeO OMe
Me
1. 2. Me 3. 4.
O
MeO OCHO Me

O
O Ph
5. 6. Ph S N 7. O
O O O

Lecture 6
CONH2
NO2 CH3
1. O 2. 3. 4. B(OR)3 5. EtNHOH
OH
OH
6. RSO3H 7. 8.
O O
OH

Lecture 7
O O
OAc
1. C 2. 3. 4. Me C O + Me C O
H
O Me Me

5. + OHC
O

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NPTEL Chemistry Reagents and Organic reactions

Lecture 8

O OOH OH
OOH
O
A. 1. 2. 3. 4. 5.

CHO

Lecture 9
O O
HO Me
Me CO2H
1. CH3CHO 2. 3. 4. CO2H 5. CHO
Me CO2Me
O

OH
CO2H
8. O 9.
6. O 7. O

Lecture 10
O
O OTBS
A. 1. O 2. OHC
O
O MeMe Me

MCPBA
MCPBA
B. NH N OH N O.

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NPTEL Chemistry Reagents and Organic reactions

Lecture 11

O O O

1. 2. 3. 4.
NHCOCH3 O
S HO
HO O
O
O Me OH

5. 6. O 7.
O
Ph Ph

Lecture 12

OH Me Me
HO OH MeO2C OH HO HO
OH
1. Ph 2 MeO2C 3. 4. 5.
Me Ph MeO2C OH HO HO
H H

O Me
HO H
O
6.
H

Lecture 13

OH OH OH O
OH
1. HO CHO + HO
OH OH OH OH

OH
CO2H
2. 3. HO2C CO2H 4.
OH OH

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NPTEL Chemistry Reagents and Organic reactions

Lecture 14
1. LAH (inverse addition) 2. LAH 3. LiAlH(OEt)3 4. LiAlH(OEt)3 5. DIBAL, Toluene, -78 oC

Lecture 15
Me
A. 1. NaCNBH3 2. NaCNBH3
OH H H H
Ph O OH N S
B. 1. OEt N
Ar 2. 3. O
N O
O O

OH O Cl H H
H H
H-BH3Na OH
CCl3 NaOH Cl Cl
C.
O O

Lecture 16
OH CO2H OEt
O
1. 2. 3. 4. 5. 6.

OH
7. 8. 9.
NH2 Ph
Br

Lecture 17

1. PtO2/ H2 2. Pd/H2 3. PtO2/H2/AcOH, 4. Raney Ni/H2, 5.

Pd/C/H2
6. H2, Wilkinson Catalyst, C6H6 7. Pd/CaCO3/H2

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NPTEL Chemistry Reagents and Organic reactions

Lecture 18
O
H
OH 5.
A. 1. 2. 3. 4. O
N O
H H
OH

Lecture 19

OH
OH O
OH O OH
1. Ph 3. HO OH + H C CH3 4.
2. 3
OEt
S

Lecture 20
OH Cl
1. OH 2. 3. 4. 5. CHO
OH
OTHP O
Br
Me

OH O O
8. 9.
6. 7.
O

Lecture 21
O
NC Me Me
O
1. 2. CH2OH 3. 4. NMe2 5. BnO OH
O
Li OH

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NPTEL Chemistry Reagents and Organic reactions

Lecture 22

MeO2C CO2Me
N O Me Me
OH
OEt
1. 2. MeO2C 3. Ph 4.
Me
Me
OLi

5. OTBDS 6. 7.

SiMe3

Lecture 23

CO2Me Me O O
CO2Me
CO2Me Me
A. B. C. Ph Et D. E. Me

OH
F. Me

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NPTEL Chemistry Reagents and Organic reactions

Lecture 24
N N H S
1. 2. N 3.
O N
Ph

OC8H17 SiMe3 O

O
4. 5. 6.

Me3Si OC8H17

Lecture 25

A. 1. BH3, H2O2/OH 2. BH3, H2O2/OH C. 1. 2.

N OH
H

B2H6 150 oC H2O2/NaOH

E. 1. BH2 OH
BH2

H thexyl H O
thexyl-BH2 B CO-H2O
2.
H2O2/NaOH
H H

Lecture 26
OH
1. (a) A Li/Me3SiCl B. MeCOCl/AlCl3 (b) C.
SiMe3 D. Ph
O
H O Ph
2. (a) (b) (c)
Me3Si SiPh3

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NPTEL Chemistry Reagents and Organic reactions

Lecture 27
SiMe3

O H
Ph Ph
O
1. 2. 3. S 4. 5. O
O Ph OH COPh
O
OMe H OBn
O

Ph3Sn O
6. 7.
O
O

Lecture 28
N N HO OAc
B. 1. 2. N 3. N 4. 5. AcO CH(CO2Me)2
N N
Ph
Ar Ar

Lecture 29
MeO2C Me
2. 3. Ph 4. Me2N Ph

O O

Ph
5. CO2Et 6. 7.

CN

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NPTEL Chemistry Reagents and Organic reactions

Lecture 30

CH3 CO2Me
1. CHO 2. F C 3.
3 CHO NEt2 4. NHAc

O
OH OH
5. Ph N N
6. 7.
Ph Ph
Ph

Lecture 31
OH
OH O O O
1. 2. 3. 4.
OH O

O
CO2Me OMe
5. HCONMe2 6. O 7. 8.
OH Et

9. Me OH

Lecture 32
OH Me OH
H
tBu CO2Me
1. 2. 3. (CO)3Cr 4. (CO)3Cr
MeO CO2Me
OMe Cr(CO)3 OH

OH
5. Me CO2Me 6. Ph 7. SnBu3
SiMe3

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NPTEL Chemistry Reagents and Organic reactions

Lecture 33
O
OH OMe OH H OTMS
NO2
1. Ph 2. 3. 4. 5. CN
H
O OAc

Lecture 34

O O
Br Br O
1. 2. 3. 4. OH
O Br Br
O O

O O
5. 6. 2 O 7.
I

Lecture 35
O
HO O
HO
HO CO2Me
1. 2. Ph 3. 4. 5. OH
OH

NHBn O
H

6. 7.
NHBn
H
O

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NPTEL Chemistry Reagents and Organic reactions

Lecture 36
Br O
1. O 4.
2. Cl 3.
Br Br Br

Br TsHN
O O
5. 6. 7.
Br Br Br
OH

Lecture 37

O O
NH HN Ph
O
O O
1. 2. 3. 4. BocHN N CO2Me
O O O H
CO2Me
O

Lecture 38
O O O O
N2 2. N2
1. EtO 3. Ph O N N2
H
O
O O O O
4. Ph O N N CO2Me 5. Ph O N OH
H H H

Lecture 39
CO2Et
1. 2. 3. Ph CHO
N
OMe

CN
OMe Ph O
4. 5. P OEt
Ph OEt

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NPTEL Chemistry Reagents and Organic reactions

Lecture 40
O
O
O OH
1. Me 3. 4.
2. 5.
OH

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