ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
4th Edition
ISBN: 9781119659556
Author: Klein
Publisher: WILEY
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Chapter 25, Problem 83PP
Interpretation Introduction

Interpretation:

For the given Boc-protection of phenylalanine, a mechanism needs to be drawn.

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 d-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

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く Predicting the pr Predict the major products of the following organic reaction: Δ Some important notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. ? Click and drag to start drawing a structure.
propose synthesis

Chapter 25 Solutions

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS

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