Cliffs AP Chemistry, 3rd Edition

Hydrolysis of amides-acid catalyzed

Hydrolysis of amides-base catalyzed

Hydrolysis of carboxylic esters — acid

catalyzed

Hydrolysis of carboxylic esters — base

catalyzed (saponifications)

Neutralization of carboxylate salts

Nitration of aromatic rings

Oxidation of alcohols

Oxidation of aldehydes

Oxidation of ketones

Oxidation of thiols 2RSH [O] RRS S

[O]

Mild

conditions

RCR'

O

Ketone

no reaction

[O] RCOH

O

RCH

O

Aldehyde Carboxylic acid

Tertiary

RCOH

[O]

R"

R'

no reaction

Secondary

RCHR' [O]

OH

RCR'

O

Primary

RCH 2 OH [O] R C H [O]

O

RCOH

O

NO 2

HNO 3

H 2 SO 4

+

RCO−+HCl

O

RCOH Cl+ −

O

RCOR'+OH−

O

RCO−+R'OH

O

H+

RCOR'+H 2 O

O

RCOH+R'OH

O

RCNHR' H OH–

+ 2 O

O

RCO−+R'NH 2

O

H+

RCNH 2 +H 2 O

O

RCOH NH+ 4 +

O

Part II: Specific Topics