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
Mechanism of the reaction:
Step by step solution
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.
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.
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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