Answer Key for Problem Set 1 1. 2. 3. 4.

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Answer Key for Problem Set 1 1. 2. 3. 4.

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Answer Key for Problem Set 1. 1. C. C. H. NaNH2. NH3(l), 33oC. C. C: O. 1. 2. H3O+. OH. OH under harsh acid conditions. 2. Br. OH. 1 eq BuLi. Et2O. Br. OLi.

Answer Key for Problem Set 1

1. C

C

OH

H C

NaNH2 NH3 (l),

C: 1.

33oC

O

2. H3 O+

OH under harsh acid conditions

2.

Br

Br 1 eq BuLi

Li 1 eq BuLi

Et2 O

O

Et2 O

OH

OLi

1.

2. NH4Cl

OH

OLi

OH (extra credit for the right stereochemistry)

3. NC

Et2CuLi I

4. CH2I2 Zn-Cu

THF, 0oC

NC

Et

5. Br Br (CH3)2CuLi

CHBr3 OH-

Et2O

6. a) Br

H

-

Cu

Cu

2

2Br

H

b) Br

-

Cu

Cu

2

7. H

H Li2 2CuCN THF, 0oC

O

OH

2Br

H

8. H

H

+

Br

1 eq BuLi

H

Li

OSiEt3 +

Br

1 eq BuLi Li

H2, Pd/CaCO3

OSiEt3

quinoline OSiEt3 CH2 I2 , Zn-Cu

TBAF OH

OSiEt3

OSiEt3

Na NH3 OSiEt3

CH2 I2 , Zn-Cu

TBAF OH

OSiEt3

9. a) H

+ 1 eq BuLi

H

H

Li

O H

Li

OH H

+

MeO

MeO

b) O

OCH3

HO Li

+

c) MgBr

I +

+

10. Br

1.

2CuCN

Li2

2. CH2I2, Zn-Cu

Br

2CuCN

2. CH2I2, Zn-Cu

Li2