Organic Chemistry

776 CHAPTER 18 Carbonyl Compounds II

g.Reaction with acetylide ions:

h.Reaction with cyanide ion:

2. Reactions of carbonyl compoundswith hydride ion donors (Section 18.5).

a.Reaction of an aldehydewith sodium borohydride forms a primary alcohol:

b.Reaction of a ketonewith sodium borohydride forms a secondary alcohol:

c.Reaction of an esterwith lithium aluminum hydride forms two alcohols:

d.Reaction of an esterwith diisobutylaluminum hydride forms an aldehyde:

e.Reaction of a carboxylic acidwith lithium aluminum hydride forms a primary alcohol:

f. Reaction of an acyl chloridewith lithium aluminum hydride forms a primary alcohol:

ROHCH 2

1. LiAlH 4


2. H 3 O+

O

C

RCl

ROHCH 2

1. LiAlH 4


2. H 3 O+

O

C

ROH

C

R

O

C

ROR′

1. [(CH 3 ) 2 CHCH 2 ] 2 AlH, − 78 °C


2. H 2 O

O

H

RCH 2 OH + R′OH

O

C

R OR′

1. LiAlH 4


2. H 3 O+

O

C RRCH

R

1. NaBH 4


2. H 3 O+

OH

R

RCH 2 OH

R

1. NaBH 4


2. H 3 O+

O

H

C

RNC C

R

−CN

HCl

OH

R

O

R

C

RCRC C

1. RC C−


2. H 3 O+

OH

R

R

O

R

C