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Chapter 21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

The document describes reactions involving carboxylic acid derivatives. It discusses nucleophilic acyl substitution reactions where an alcohol reacts with a carboxylic acid to form an ester and a carboxylate ion. It also describes similar reactions where an amine reacts with an ester to form an amide and an alcohol. The document provides examples of hydrolysis, reduction, and anhydride formation reactions.

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172 views20 pages

Chapter 21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

The document describes reactions involving carboxylic acid derivatives. It discusses nucleophilic acyl substitution reactions where an alcohol reacts with a carboxylic acid to form an ester and a carboxylate ion. It also describes similar reactions where an amine reacts with an ester to form an amide and an alcohol. The document provides examples of hydrolysis, reduction, and anhydride formation reactions.

Uploaded by

張湧浩
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Chapter 21.

Carboxylic Acid
Derivatives: Nucleophilic Acyl
Substitution Reactions
21.1 O O
CH3OH
C C
CH3CH2 O CH2CH3

• Ethanoic acid + ethanol


• methyl ethanoate + Propanoic acid
• ethyl ethanoate + Ethanoic acid
• methyl propanoate + Propanoic acid
• ethyl propanoate + Ethanoic acid
21.1 answer
• Ethanoic acid + ethanol
• methyl ethanoate + Propanoic acid
• ethyl ethanoate + Ethanoic acid
• methyl propanoate + Propanoic acid
• ethyl propanoate + Ethanoic acid

An anhydride reacts with an alcohol to give a carboxylic acid


and an ester.
Alcoholysis 醇解
O
21.2
CH3CH2CH2NH2
C
CH3CH2 OCH3

• N-Propyl propanamide + methanol


• N-Propyl ethanamide + ethanol
• N-Ethyl propanamide + methanol
• N-Ethyl ethanamide + ethanol
• N-Ethyl ethanamide + propanol
Level 3
Challenging
21.2 answer

• N-Propyl propanamide + methanol


• N-Propyl ethanamide + ethanol
• N-Ethyl propanamide + methanol
• N-Ethyl ethanamide + ethanol
• N-Ethyl ethanamide + propanol
Aminolysis 胺解
An ester reacts with an amine to produce an amide
and an alcohol.
Level 3
Challenging
O
21.3 HCl
C
CH3CH2 NHCH3 heat

O
O
(a) (b)
NH2
H

(c) CH3COOH (d)


COOH
21.3 answer
O
O
(a) (b)
NH2
H

(c) CH3COOH (d)


COOH

Hydrolysis 水解
21.4
Predict the outcome of the following
reaction.
O

OH SOCl2

1. 2. 3.
O O
OH
H Cl

4. 5.
O
O
S
OH S OH
O
21.4 answer
O

OH SOCl2

1. 2. 3.
O O
OH
H Cl

4. 5.
O
O
S
OH S OH
O
O
21.5 1. 2CH3MgBr
C
+
CH3CH2 Cl 2. H3O

(a) (b)

HO
OH

(c) (d)

OH HO
21.5 answer

(a)
(b)
HO
OH

(c) (d)

OH HO
21.6 O
1) LiAlH4

NH2 2) H2O

O
(a) COOH (b)

NH2

(d)
(c)
CH2NH2 CH2NHCH3
21.6 answer

O
(a) COOH (b)

NH2

(d)
(c)
CH2NH2 CH2NHCH3
21.7 O
1) LiAlH4

NHCH3 2) H2O

O
(a) COOH (b)

NH2

(d)
(c)
CH2NH2 CH2NHCH3
21.7 answer

O
(a) COOH (b)

NH2

(c) (d)
CH2NH2 CH2NHCH3
O O
21.8
C C
CH3CH2 Cl
+ -
HO CH3

a.Ethanoic methanoic anhydride


b.Methanoic propanoic anhydride
c.Ethanoic anhydride
d.Ethanoic propanoic anhydride
21.8 Answer

a.Ethanoic methanoic anhydride


b.Methanoic propanoic anhydride
c.Ethanoic anhydride
d.Ethanoic propanoic anhydride

An acid halide reacts with a carboxylic acid


to form an anhydride.
21.9
What sequence of reagents will accomplish the
following transformation?
OH
OH

1. 2.
+ +
H 2 PhMgBr H3O H3O+
2 PhMgBr
CH3OH Et2O Et2O

3. 4.
H+ H+ 2 PhOH

PhOH CH3OH

5.
SOCl2 2 PhOH
21.9 answer
OH
OH

1.
+
2.
H +
2 PhMgBr H3O 2 PhMgBr H3O+

CH3OH Et2O Et2O

3. 4.
H+ H+ 2 PhOH

PhOH CH3OH

5.
SOCl2 2 PhOH
1.

5.

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