Answered: Aromatic heterocycles can undergo…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Aromatic heterocycles can undergo electrophilic aromatic substitution like benzene. Groups attached to the heterocycle can therefore have similar directing effects as they can on benzene. Keeping this in mind, consider the following reaction, where E+ is a general electrophile:

a) Draw all relevant resonance structures for the intermediate of each product

b) Based on your answers to part a), which product do you expect to be the major product and why? (2 points)
c) If you performed this reaction in the laboratory, which instrumental technique (ex: 1H NMR, IR, Mass Spectrometry) would be best to determine which product you obtained of the three and why?

2. Aromatic heterocycles can undergo electrophilic aromatic substitution like benzene.
Groups attached to the heterocycle can therefore have similar directing effects as they can
on benzene. Keeping this in mind, consider the following reaction, where E+ is a general
electrophile:
.S
E+
.S.
E-
or
or
Br
Br
E
Br
Br
A
a) Draw all relevant resonance structures for the intermediate of each product.
Product A:
.S.
Br
Product B:
.S.
E
Br
Product C:
E-
(+)
Br

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