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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

Propose a mechanism for the formation of 9-hydroxynonanoic acid lactone, as show in the preceding figure.

Show how you would use anhydrides to synthesize the following compounds. In each

case, explain why an anhydride might be preferable to an acid chloride.

(d) succinic acid monomethyl ester

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

Show how you would use anhydrides to synthesize the following compounds. In each

case, explain why an anhydride might be preferable to an acid chloride.

(b) n-octyl acetate

Show how you would synthesize each compound, starting with an ester containing nomore than eight carbon atoms. Any other necessary reagents may be used.

g. PhCH2COOHCH32
See all solutions

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