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Chapter 22: Q5Pc (page 1155)

Predict the major products of the following reactions.

c)

Short Answer

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c)

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01

Alkylation of enolate ions

When enolates are alkylated directly with LDA, it produces the best yields when one kind of alpha hydrogen is substituted by an alkyl group. Aldehydes are not good for direct alkylation as they lead to side reactions.

02

Predicting the major products of the reaction

(c) The given compound reacts with LDA and to form a product where the methyl group is attached to the five-membered ring. The reaction is given below:

Product formed in reaction (c)

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Most popular questions from this chapter

In Solved Problem 22-9, the target molecule was synthesized using a Michael addition to form the bond that is β,γ to the upper carbonyl group. Another approach is to use a Michael addition to form the bond that isβ,γto the other (lower) carbonyl group. Show how you would accomplish this alternative synthesis.

Propose a mechanism for the conjugate addition of a nucleophile (Nuc:-) to acrylonitrile (H2C=CHCN) and to nitroethylene. Use resonance forms to show how the cyano and nitro groups activate the double bond toward conjugate addition.

Question: Predict the products of the following reactions

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