Organic Chemistry

Summary of Reactions 873

c.

2. Reduction of alkynes to alkenes (Section 20.1).


3. Reduction of carbonyl compounds with reagents that donate hydride ion (Section 20.1).

a. e.

b. f.

c. g.

d. h.

4. Oxidation of alcohols (Section 20.2).

RCH

O

primary alcohols

secondary alcohols

RCH 2 OH

H 2 CrO 4

Na 2 Cr 2 O 7

RCR

O

H 2 SO 4

RCH

O

RCH

O

RCHR

OH

RCR

O

RCHR

OH

RCH 2 OH

RCH 2 OH

PCC

CH 2 Cl 2

further

oxidation RCOH

O

O

ClC CCl

O O

2. triethylamine

, − 60 °C

CH 3 SCH 3 , , − 60 °C

O

ClC CCl

O O

1.

1. CH 3 SCH 3 ,
   2. triethylamine

[]

RCCl

1. LiAl[OC(CH 3 ) 3 ] 3 H, − 78 °C


2. H 2 O

O

RCH

O

RCOR′

1. [(CH 3 ) 2 CHCH 2 ] 2 AlH, − 78 °C


2. H 2 O

O

RCH

O

+ R′OH

RCNHR′

1. LiAlH 4


2. H 2 O

O

RCCl RCH 2 OH RCH 2 NHR′

1. NaBH 4


2. H 3 O+

O

RCOR′

1. LiAlH 4


2. H 3 O+

O

RCR RCHR RCH 2 OH + R′OH

1. NaBH 4


2. H 3 O+

O OH

RCOH

1. LiAlH 4


2. H 3 O+

O

RCH RCH 2 OH RCH 2 OH

1. NaBH 4


2. H 3 O+

O

H 2

Lindlar

catalyst

RC CR CC

HH

R R

Na or Li

RC CR NH 3 (liq) CC

H R

R H

RCCl + H 2 RCH

partially

deactivated

Pd

O O

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