Chapter 22: Q12P (page 1161)
Propose a mechanism for the reaction of cyclohexyl methyl ketone with excess bromine in the presence of sodium hydroxide.
Short Answer

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Chapter 22: Q12P (page 1161)
Propose a mechanism for the reaction of cyclohexyl methyl ketone with excess bromine in the presence of sodium hydroxide.

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Propose a mechanism for the crossed Claisen condensation between ethyl acetate and ethyl benzoate.
When propionaldehyde is warmed with sodium hydroxide, one of the products is 2-methylpent-2-enal. Propose a mechanism for this reaction.
Question:Show how you would use an aldol, Claisen, or another type of condensation to make each compound
d.

(a) Although the following compound is a substituted acetone derivative, it cannot be made by the acetoacetic ester synthesis. Explain why (two reasons).

(b) The use of LDA to make enolate ions (Sections 22-2B and 22-3) has provided alternatives to the acetoacetic ester synthesis. Show how you might make the compound shown in part (a), beginning with 1,3-diphenylacetone.
(c) Enamine reactions (Section 22-4) occur under relatively mild conditions, and they often give excellent yields of compounds like the one shown in part (a). Show how you might use an enamine reaction for this synthesis, beginning with 1,3-diphenylacetone.
Predict the products of self-condensation of the following esters.
(a) methyl propanoate +
(b) ethyl phenylacetate + NaOCH2CH3
(c)

(d)

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