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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

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

Complete the mechanism for this acid-catalyzed transesterification by drawing out all the individual steps. Draw the important resonance contributors for each resonance stabilized intermediate.

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

(a)phenylaceticacidphenylacetonitrile

(b)phenylaceticacid→3-phenylpropionitrile

(c)p-chloronitrobenzenep-chlorobenzonitrile

An unknown compound of the molecular formula C5H9NO gives the IR and NMR spectra shown here. The broad NMR peak at d 7.55 disappears when the sample is shaken with D2O . Propose a structure, and show how it is consistent with the absorptions in the spectra.

Show how you would accomplish the following syntheses using amides as intermediates.

You may use any necessary reagents.

(a)benzoicacid→benzyldimethylamine
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