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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Section
BuyFindarrow_forward

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079
Textbook Problem

Which of the following is an incorrect characterization for a lactone?

  1. a. It is a heterocyclic compound.
  2. b. It is a cyclic ester.
  3. c. It is a cyclic ketone.
  4. d. no correct response

Interpretation Introduction

Interpretation:

Incorrect characterization of lactone has to be chosen among the given options.

Concept Introduction:

Esters are prepared by condensation of carboxylic acid with an alcohol.  A molecule of water is lost on this reaction.  The reaction that takes place in producing esters is known as esterification reaction.

Esterification reaction is the one in which the carboxylic acid is condensed with an alcohol (or phenol) in presence of strong acid catalyst to produce ester.  The general reaction scheme can be given as,

Organic And Biological Chemistry, Chapter 5.11, Problem 3QQ

In the above reaction, hydroxyl group is lost from carboxylic acid and hydrogen is lost from alcohol molecule to form water as the byproduct.

If the considered compound is a hydroxyacid, then there is a possibility of intermolecular esterification reaction.  The product obtained in this case is a cyclic ester.  Cyclic esters contain an oxygen atom in the ring and a carbonyl group also.

Explanation

Reason for correct option:

Cyclic ester is formally known as lactones.

Cyclic ester is formed by intermolecular esterification of hydroxyacid.  Cyclic ester contains an oxygen atom in the ring similar to cyclic ethers.

Cyclic ester is not a cyclic ketone.  Even though it has a ketone group in the ring, it is a part of the ester functional group.  Hence, the characterization of cyclic ester as cyclic ketone is incorrect.

Therefore the correct option is identified as option (c).

Reason for incorrect option:

Option (a) tells that the incorrect characterization of lactone is that it is a heterocyclic compound...

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