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Carbonyl Condensation Reactions Explained

This document summarizes carbonyl condensation reactions including aldol reactions, Claisen condensations, Michael additions, and Robinson annulations. Specific reactions are given to predict products and identify starting materials. Intramolecular reactions like aldol condensations and Robinson annulations are also discussed. Key reaction types covered include addition, condensation, and dehydration reactions of carbonyl compounds.

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255 views19 pages

Carbonyl Condensation Reactions Explained

This document summarizes carbonyl condensation reactions including aldol reactions, Claisen condensations, Michael additions, and Robinson annulations. Specific reactions are given to predict products and identify starting materials. Intramolecular reactions like aldol condensations and Robinson annulations are also discussed. Key reaction types covered include addition, condensation, and dehydration reactions of carbonyl compounds.

Uploaded by

張湧浩
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd

Chapter 23.

Carbonyl
Condensation Reactions
23.1
Predict the aldol reaction product of the following
ketone.
O NaOH
2 aldol product
Ethanol

1. 2.
O OH
O OH

3. 4.
O
O OH

HO

5.
O
OH
23.1 answer
O NaOH
2 aldol product
Ethanol

1. 2.
O OH
O OH

3. 4.
O
O OH

HO

5.
O
OH
23.2 O
OH
2 C Enone product
CH3CH2 H heat
(a) (b)
H

O O

(c) (d)
H
H

O
O
23.2 answer
(a) (b)
H

O O

(c) (d)
H
H

O
O
23.3 Which starting material(s) will produce the
following aldol reaction product?

2.
1.

3.
4.
2

5.

2
23.3 answer
 

2.
1.

2

3.
4.
2

5.

2
23.4 Which pair of compounds would be required to
prepare the following aldol product?

2.
1. O O
O
O H +
H + O

4.
3. O
O O
H +
+ O
H

5.
O

H +
O
23.4 answer 

2.
1. O O
O
O H +
H + O

3. 4.
O
O O
+
H +  H O

5.
O

H +
O
23.5 Which of the following reactions will yield the
compound shown below?

1. 2.

3.
4.

5.
23.5 answer 

1. 2.

3.
4.

intramolecular aldol condensation

5.
O
23.6
NaOCH3
2 C
CH3CH2 OCH3

(a) OCH3
(b)
OCH3
OCH3

O O
O

(c) (d) O

O
OCH2CH3
OCH3

O O

O
23.6 answer
(a) OCH3
(b)
OCH3
OCH3

O O
-keto ester
O

(c) (d) O

O
OCH2CH3
OCH3

O O
O

A -keto ester is produced from a Claisen


condensation.
O

23.7 OH
+

O O
O

(a) (b)

O O
O

(c) O O
(d) O

O
O
23.7 answer
O

(a) (b)

O O
O
(c) O O
(d) O

O
O

The Michael Reaction:


the -diketone undergoes an 1,4-addition.
23.8 Predict the outcome of the following reaction.

2.
1.

3. 4.

5.
23.8 answer

2.
1.

3. 4.

5. The Michael Reaction:


Enamines undergoes an
1,4-addition
O
23.9
OH
+ Robinson
heat annulation
O O
O

(a) (b)

O O
O
(c) O O
(d)

O O
23.9 answer
O

(a) (b)

O O
O
(c) O O
(d)

O O
In the Robinson annulation, (1) Michael reaction (1,4-
addition) (2) the -diketone undergoes an
intramolecular aldol condensation, followed by
dehydration.

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