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Chapter 17: Q22P (page 820)

What product is obtained from the aldol condensation of cyclohexanone?

Short Answer

Expert verified

A reaction followed as:

Step by step solution

01

Aldol condensation

It is defined as the reaction which forms the 尾-hydroxy aldehyde or 尾 -hydroxy ketone on reacting the enol or enolate ion with the carbonyl group in presence of NaOH.

02

Aldol condensation of cyclohexanone

The two moles of cyclohexanone react with each other and form hydroxy aldehyde. In the reaction the 1 mole of cyclohexanone -CH group which behave as a nucleophile to the another mole of cyclohexanone carbonyl carbon. Followed by the water leads to the elimination of the hydroxyl group and the double bond is generated between two rings as shown below:

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Most popular questions from this chapter

Describe how the following compounds could be prepared from cyclohexanone using an enamine intermediate:

a.

b.

Using cyclopentanone as the reactant, show the product of a. acid-catalyzedketo鈥揺nolinterconversion. b. an aldol addition. c. an aldol condensation.

Starting with methyl propanoate, how could you prepare 4-methyl-3-heptanone?

An aldol addition can be catalyzed by acids as well as by bases. Propose a mechanism for the acid-catalyzedaldol addition of propanal.

Draw the products of the following reactions:

a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl

b. pentanoic acid + PBr3 + Br2, followed by hydrolysis

c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl

d. diethyl 2-ethylhexanedioate: (1) sodium ethoxide; (2) HCl

e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + 鈭�

f. acetophenone + LDA/THF: (1) slow addition of diethyl carbonate; (2) HCl
See all solutions

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