Modified Mastering Chemistry with Pearson eText -- Standalone Access Card -- for Organic Chemistry (8th Edition)
Modified Mastering Chemistry with Pearson eText -- Standalone Access Card -- for Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134261430
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 19, Problem 27P

Benzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a Lewis acid such as AlCl3.

  1. a. What are the major and minor products of the following reaction?
  2. b. Would you expect epoxides to undergo similar reactions?

Chapter 19, Problem 27P, Benzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a

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1. Br₂, PBrg 2. H₂O H₂C OH H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br₂ reacts in an α- substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H3C :0: :0::Br: Br Br H3C CO-P H Br Br
Benzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a Lewis acid such as AlCl3.a. What are the major and minor products of the following reaction?b. Would you expect epoxides to undergo similar reactions?
Rank the compounds according to their increasing reactivity toward electrophilic substitution. 1. Benzaldehyde 2. o-dimethylbenzene 3. nitrobenzene 4. phenol

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Modified Mastering Chemistry with Pearson eText -- Standalone Access Card -- for Organic Chemistry (8th Edition)

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