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Chapter 21: Q60P (page 1142)

Explain this curious result. What does this reaction tell you about the relative reactivity of esters and ketones?

Short Answer

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Mechanism for reaction

Formation of the desired product

Step by step solution

01

The mechanism for the reaction

The product combination indicates that the ketone is more reactive as compared to the ester. Therefore, as soon as a small amount of ketone is formed, further attack by Grignard reagent takes place, although an excess amount of ester remains unreacted.

Mechanism for reaction

02

Formation of product

The low reactivity of ester can be attributed to the resonance of the oxygen lone pair with the carbonyl group, which decreases the electron deficiency of the carbonyl carbon.

Formation of the desired product

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Most popular questions from this chapter

What characteristics of the phenyl propanoate spectrum rule out an aldehyde or carboxylic acid functional group giving the absorption at 1730 cm-1?

Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.

(a) ethyl propionate

(b)phenyl 3-methylhexanoate

(c)benzyl benzoate

(d)cyclopropyl cyclohexanecarboxylate

(e)tert-butyl acetate

(f) diallyl succinate

Which of the following proposed reactions would take place quickly under mild conditions?

A chemist wanted to make the ethyl ester of 2-formylbenzoic acid, but the spectra of the product did not meet her expectations. The IR of product Z had an ester carbonyl, but no aldehyde absorption nor any absorption in the OH region. The HNMR data are given. What is the structure of Z? Propose a mechanism for its formation.

(a)Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize

(i) benzyl acetate and

(ii) N,N-diethylacetamide.

(b)Propose a mechanism for each synthesis in part (a).
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