Complete the following reactions.

a)
O

MgBr 2) H3O

enantiomer
+

OH

b)
CH2 CH2 OH

O OH

K2CrO4

H2SO4

CH2

NH3

CH2

NH4

c)

(CH3(CH2)4)2CuLi

OH

enantiomer 2) H3O
+

d)

HO O

TBDMS-Cl imidazole

Si O O

Li

HO

*
OH

2) H3O

3)( CH3CH2CH2CH2)4N+ F-

diastereomer

e)

CH2 OH

CH2 CH2

OH

excess PCC
O

f)

HO

DIBAL-H 2) H3O
+

O HO O

Aldehyde formed from ester or acid chloride

g)

HO

1) NaBH4 2) H3O
+

O HO

* OH

*isomers here

h)

C C H

NaNH2

C C O

OH

2) H3O+

C C

i)

CH3

CH2

C O CH3

CH3

OH CH3 CH2 CH3

2 CH3 C MgI
CH3

2) H3O

CH3 C C CH3 CH3 C CH CH3 3

KMnO4, KOH 2) H3O

+

no Reaction
O H C OH

CH3OH

j)
CH3 CH2

O C O CH3

LiAlH4 2) HOH
CH3 CH2 CH2 OH HO CH3

k)
C C CH2 CH2 CH3

O HO C CH2 CH2 CH3

O3 2) HOH

C OH

l)
Cl

AlCl3

KMnO4

no reaction since 3o C's don't oxidize; otherwise would make benzoic acid!

m)

OH

(CH3CH2)2CuLi

K2Cr2O7 diastereomer

2) H3O+

n)
H3C O

excess
O O

LiAl(OtBu)3H 2) H3O+
H

O O CH3 MgI

2) HOH

H HO

* diastereomer

OH

CH3OH

o)

O MgCl

CO2

2) H3O+

C OH

C6H5-Li 2) HOH

C OH

LiAlH4 2) HOH

CH2 OH

1) deprotonate acid 2) reprotonate

H C CH2 OH

1) Mg
CH2 Br C H O

PCC, CH2Cl2

2) HOH

enantiomer