Cliffs AP Chemistry, 3rd Edition

Preparation of amides from acyl
chlorides and ammonia or amines

Preparation of amides from
anhydrides and ammonia or amines

Preparation of amides from carboxylic
acids and ammonia or amines
(with DCC-dicyclohexylcarbodiimide)

Preparation of carboxylic esters from
acylchlorides and alcohols

Preparation of carboxylic esters from
anhydrides and alcohols

Preparation of carboxylic esters from
carboxylic acids and alcohols

Reaction of amines with acids
Primary Primary RNH 2 + HCL→ RNH 3 + Cl–
Secondary Secondary R 2 NH + R'COOH→R 2 NH 2 + R'COO–
Tertiary Tertiary R 3 N + HNO 3 → R 3 NH + NO 3 –

Reaction of amines with nitrous acids
Primary Primary RNH 2 + HONO→N 2 + other products
Secondary Secondary R 2 NH + HONO→R 2 NNO

Reaction of carboxylic acids with bases

Reaction of tertiary
amines with alkyl halides

Reduction of aldehydes

Reduction of disulfides R
R S S [H] 2RSH

H

[H]

R C RCH 2 OH

O

Aldehyde Primary alcohol

R 3 N R'Cl++RNR'

R

R

Cl−

R C OH++NH 3 RCO−

O O

NH 4 +

R C OH++OH− RCO−

O O

H 2 O

R C OH++R'OH RCOR'

O O

H+

H 2 O

R C OCR+R'OH RCOR'+R

O

C OH

O O O

R C Cl+R'OH RCOR'+HCl

O O

R C OH++R'NH 2 DCC RCNH R'+DHU

O O

R C OCRNH+ 3 RCNH 2 +R

O

C OH

O O O

RCCl+R' 2 NH RCNR' 2 +HCl

O O

Writing and Predicting Chemical Reactions