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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Chapter
Section
BuyFindarrow_forward

Organic And Biological Chemistry

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

Which of the following directly influences the proton-acceptor behavior (basicity) of the nitrogen atom in a amide functional group?

  1. a. partial positive charge on the carbonyl carbon atom
  2. b. partial negative charge on the carbonyl carbon atom
  3. c. partial positive charge on the carbonyl oxygen atom
  4. d. no correct response

Interpretation Introduction

Interpretation:

The proton-acceptor behavior of nitrogen atom in amide functional group is directly influenced by what has to be chosen from the given options.

Concept Introduction:

Amides have a carbonyl group bonded to the nitrogen atom.  The carbonyl carbon atom pulls the lone pair of electrons present on the nitrogen strongly.  Hence, the nitrogen atom cannot act as a proton acceptor.  Amides are not basic in nature.

Explanation

Reason for correct option:

Amides have a nitrogen atom that is bonded to a carbonyl group.  The carbonyl carbon atom pulls the lone pair of electrons on nitrogen towards itself.  Hence, amides cannot act as proton acceptor.  The carbonyl carbon possesses a partial positive charge and the oxygen atom possesses a partial negative charge.  Due to this partial positive charge on carbon atom, the lone pair of electrons are not free.  Therefore, amines are basic in nature while amides are not.

Hence, option (a) is a correct one.

Reason for incorrect option:

Option (b) tells that partial negative charge on the carbonyl carbon atom influences directly the proton-acceptor behavior of amide...

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