Advices For Studying Organic Chemistry

CO Et^2 O 2

2 H LiAlH 4 CH 2 O)Al]Li

Li 2 SO 4

H 2 O/H 2 SO 4

CH 2 OH Al 2 (SO 4 ) 3

R [(R 4 H 2 LiAlO 2

Lithium

aluminum

hydride

4 +^3

4 + +

+ 4 +

R

C CO 2 H CH 2 OH

LiAlH 4 /Et 2 O

H 2 O/H 2 SO 4

CH 3

H 3 C

CH 3

C

CH 3

H 3 C

CH 3

1.

2.

2,2-Dimethylpropanoic acid Neopentyl alcohol

92%

3. Esters can be reduced by high-pressure hydrogenation (a reaction preferred for
   industrial processes and often referred to as “hydrogenolysis” because the C–O
   bond is cleaved in the process), or through the use of LiAlH 4.

R COR'

O

++ H 2 CuO-CuCr 175 oC^2 O^4 RCH 2 OH R'OH

5000 psi

1. LiAlH 4 /Et 2 O
   COR' H 2 O/H 2 SO 4

O

R 2. RCH 2 OH + R'OH

1) The latter method is the one most commonly used now in small-scale laboratory

syntheses.

4. Aldehydes and ketones can be reduced to alcohols by hydrogenation, or sodium in
   alcohol, and by the use of LiAlH 4.

1. The most often used reducing agent is sodium borohydride (NaBH 4 ).

R CH

O

4 + NaBH 4 +R 3 H 2 O^4 CH 2 OH + NaH 2 BO (^3)
H 3 CH 2 CH 2 C CH
O
NaBH 4
H 2 O CH^2 OH
CH 3 CH 2 CH 2
Butanal 85% 1-Butanol