EBK ORGANIC CHEMISTRY-PRINT COMPANION (
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
Question
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Chapter 25, Problem 76PP

(a)

Interpretation Introduction

Interpretation:

The product formed when L-valine is treated the given set of reagents need to be predicted.

Concept introduction:

Esterification is a process in which a carboxylic acid reacts with an alcohol in presence of acid to form an ester by loss of water molecule.  The general scheme of Fischer esterification can be shown as,

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 25, Problem 76PP

(b)

Interpretation Introduction

Concept introduction:

Boc-protection of amino group in amino acids is an important reaction in peptide chemistry.  This prevents the amino group from involving additional reactions forming by-products.  The nitrogen atom of carbamate is less nucleophilic than the nitrogen atom of amine because its lone pair is delocalized by the neighboring carboxyl group.  Boc-protection can be done by reaction of amino acid with di-tert-butyl dicarbonate.  The steps involved in Boc-protection of amino acid are,

  • Nucleophilic attack to form tetrahedral intermediate
  • Loss of leaving group to reform carbonyl
  • Proton transfer to give protected amino acid

(c)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively.  Deprotonation or protonation can occur depending upon the conditions.  The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

(d)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively.  Deprotonation or protonation can occur depending upon the conditions.  The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

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Chapter 25 Solutions

EBK ORGANIC CHEMISTRY-PRINT COMPANION (

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