H H3C N. N. H3C. N. AICI 3 N-phenylacetamide

Chemistry for Today: General, Organic, and Biochemistry
9th Edition
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Chapter16: Amines And Amides
Section: Chapter Questions
Problem 16.72E: The stimulant in coffee is: a. tannic acid b. theobromine c. theophylline d. caffeine
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Consider the Friedel-Crafts (FC) alkylation of N-phenylacetamide (shown below) in which a reaction with 1-chloropropane and AlCl3 produces two isomers of isopropyl N-phenylacetamide.

1. Draw the complete reaction mechanism for the formation of the ortho product (para is also formed).

2. Is this reaction faster or slower than the similar FC reaction starting with benzene (C6H6)? Explain why.

3. Explain why this reaction produces the ortho and para products (but not meta). 

Use your mechanism to help explain parts #2 and #3. Use additional drawings and words as needed. 

H
H3C N.
N.
H3C.
N.
AICI 3
N-phenylacetamide
Transcribed Image Text:H H3C N. N. H3C. N. AICI 3 N-phenylacetamide
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