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Chapter 21: Q14P (page 1107)

Propose a mechanism for the following ring-opening transesterification. Use the mechanism in Problem 21-13 as a model.

Short Answer

Expert verified

Mechanism of the reaction:

Step by step solution

01

About the first reactant:

The first reactant contains one oxygen atom in the ring of cyclohexane and another oxygen atom bonded to the ring.

The name of this compound is tetrahydro-2H-pyran-2-one.

02

About methanol:

The given second reactant CH3OH is methanol. It the simplest alcohol and is used as a solvent in the synthesis of organic chemicals that has wide industrial applications.

03

Mechanism of the reaction:

The lone pairs of electrons present on the oxygen atom of carbonyl carbon of cyclic structure attack the acidic hydrogen.

This will give resonance structures. After several rearrangements, a reaction with methanol takes place leading to the formation of the desired product.

The mechanism is given below.

Mechanism of the reaction

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Most popular questions from this chapter

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.

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b.

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e.

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Show how you would convert the following starting materials to the indicated nitriles:

(a)phenylaceticacidphenylacetonitrile

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Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.(a)N-ethylbenzamide鈫�benzylethylamine

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

a. PH3C-OH
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