Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 11, Problem 47P
Interpretation Introduction

Interpretation:

The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed.

Concept introduction:

Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride.

Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl group of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

Example:

  Essential Organic Chemistry (3rd Edition), Chapter 11, Problem 47P

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1) Calculate the longest and shortest wavelengths in the Lyman and Paschen series. 2) Calculate the ionization energy of He* and L2+ ions in their ground states. 3) Calculate the kinetic energy of the electron emitted upon irradiation of a H-atom in ground state by a 50-nm radiation.
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Essential Organic Chemistry (3rd Edition)

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