Organic Chemistry

874 CHAPTER 20 More About Oxidation–Reduction Reactions

5. Oxidation of aldehydes and ketones (Section 20.3).

a. aldehydes

b.ketones

6. Oxidation of alkenes (Sections 20.4, 20.6, 20.8).

a.

b.

c.

7. Oxidation of 1,2-diols (Section 20.7).


8. Oxidation of alkynes (Section 20.9).

a. c.

b. RCOH

O O

RC CR′ 2. H + R′COH

2 O

1. O 3 , − 78 °C

RCOH

O

RC CH 2. H + CO 2

2 O

RC 1. O^3 , −^78 °C

O O

RC CR′ HO− CR′

KMnO 4

RCR

O

CHR′ R′CH

O

HIO 4

+

OHOH

RC

R

RCR

O

CHR′ R′CH

O

HIO 4

+

OHOH

RC

R

RC CHR′

R

CHR′

R

RC

O

cold

KMnO 4 , HO−, H 2 O

RCR + R′CH

OO

CHR′

HIO 4

OHOH

RC

R

2. H 2 O 2


3. OsO 4

RCOOH

O

RCR

O

R′COH

O

KMnO 4 , H+

RC CHR′ +

R

RCR

O

R′CH

O

RC CHR′

R

1. O 3 , − 78 °C


2. Zn, H 2 O
   or
   (CH 3 ) 2 S

+

RCR

O

R′COH

O

1. O 3 , − 78 °C
   2. H 2 O 2 +

RCR

O

RCOR

O

R’COOH

O

R′COH

O

+

RCH

O

RCOH

O

R’COOH

O

R′COH

O

+

RCH

O

metallic

silver

RCH

O

1. Ag 2 O, NH 3
   2. H 3 O+

Na 2 Cr 2 O 7

H 2 SO 4 RCOH

O

RCOH + Ag

O

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