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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

Problem: starting with bromocyclohexane, how can each of the following compounds be prepared?

Propose a mechanism for the following reaction:

A ketone undergoes acid-catalyzed bromination, acid-catalyzed chlorination, racemization, and acid-catalyzed deuterium exchange at the 伪-carbon. All of these reactions have similar rate constants. What does this tell you about the mechanisms of these reactions?

How many stereoisomers are obtained from each of the synthesis described in Problem 14?

The 1 H NMR chemical shifts of nitromethane, dinitromethane, and trinitromethane are at d 6.10, d 4.33, and d 7.52. Match each chemical shift with the compound. Explain how chemical shift correlates with pKa.
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