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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

An ether extraction of nutmeg gives large quantities of triolein, a waxy crystalline solid of melting point 57 °C. The IR spectrum of triolein shows a very strong absorption at1735 cm-1 . Basic hydrolysis of triolein gives 1 equivalent of glycerol and 3 equivalents of oleic acid ((9Z)-Octadec-9-enoic acid).

(a) Draw the structure of triolein.

(b) Predict the products formed when triolein is treated with lithium aluminum hydride, followed by aqueous hydrolysis of the aluminum salts.

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.

d.Ph2CHOH

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

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

(a)phenylaceticacidphenylacetonitrile

(b)phenylaceticacid→3-phenylpropionitrile

(c)p-chloronitrobenzenep-chlorobenzonitrile

Show how you would use anhydrides to synthesize the following compounds. In eachcase, explain why an anhydride might be preferable to an acid chloride.

(a) n-octylformate
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