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Chapter 22: Q.69-F (page 1204)

Question: Predict the products of the following reactions

f.

Short Answer

Expert verified

Answer

Step by step solution

01

Claisen ester condensation

In this sodium ethoxide is used for condensation to avoid the transesterification. Ethoxide is the base which protonate the acidic hydrogen to form 尾keto ester.

02

Formation of the product followed by alkylation

Ethoxide is used as base to form enolate ion which form keto ester on further reaction with the alkyl halide the alkylation occur means the by removal of halide ion the alkyl group attached at the alpha position to the carbonyl.

03

Mechanism

  1. Acidic hydrogen protonated
  2. Formation of the enolate ion
  3. Alkylation

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Most popular questions from this chapter

Question:Show how you would use the Robinson annulation to synthesize the following compounds

Question:Show how you would use the Robinson annulation to synthesize the following compounds.

C.

Many of the condensations we have studied are reversible. The reverse reactions are often given the prefix retro-, the Latin word meaning 鈥渂ackward.鈥� Propose mechanisms to account for the following reactions.

a.

b.

c.

d.

(A true story.) Chemistry lab students added an excess of ethyl magnesiumbromide to methyl furoate, expecting the Grignard reagent to add twice and form the tertiary alcohol. After water workup, they found that the product was a mixture of two compounds. One was the expected product having two ethyl groups, but the unexpected product had added three ethyl groups. Propose a mechanism to explain the formation of the unexpected product.

Show how cyclohexanone might be converted to the following 未- diketone .
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