4 pts total) re is Aromatic (A), (circle one) A AAN ion with Cl₂/FeCls. (6 pts) acids shown to right) (6 pts) al 3 1. Consider the Friedel-Crafts (FC) alkylation of N-phenylacetamide (shown below) in which reaction with 1-chloropropane and AlCl3 produces two isomers of isopropyl N-phenylacetamide. (20 pts) 1. Draw the complete reaction mechanism for the formation of the ortho product (para is also formed) (10 pts) 2. Is this reaction faster or slower than the similar FC reaction starting with benzene (C6H6)? Explain why. (4 pts) 3. Explain why this reaction produces the ortho and para products (but not meta). (6 pts) Use your mechanism to help explain parts #2 and #3. Use additional drawings and words as needed. to AICI N-phenylacetamide 455 sta AHO O 00 10H СОИН 08H НИ MOHO HO HO 10

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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4 pts total)
re is Aromatic (A),
(circle one)
A AAN
ion with Cl₂/FeCls. (6 pts)
acids shown to right) (6 pts)
al
3
1. Consider the Friedel-Crafts (FC) alkylation of N-phenylacetamide (shown below) in which reaction with
1-chloropropane and AlCl3 produces two isomers of isopropyl N-phenylacetamide. (20 pts)
1. Draw the complete reaction mechanism for the formation of the ortho product (para is also formed) (10 pts)
2. Is this reaction faster or slower than the similar FC reaction starting with benzene (C6H6)? Explain why. (4 pts)
3. Explain why this reaction produces the ortho and para products (but not meta). (6 pts)
Use your mechanism to help explain parts #2 and #3. Use additional drawings and words as needed.
to
AICI
N-phenylacetamide
455
sta
AHO O
00 10H
СОИН
08H
НИ
MOHO HO
HO
10
Transcribed Image Text:4 pts total) re is Aromatic (A), (circle one) A AAN ion with Cl₂/FeCls. (6 pts) acids shown to right) (6 pts) al 3 1. Consider the Friedel-Crafts (FC) alkylation of N-phenylacetamide (shown below) in which reaction with 1-chloropropane and AlCl3 produces two isomers of isopropyl N-phenylacetamide. (20 pts) 1. Draw the complete reaction mechanism for the formation of the ortho product (para is also formed) (10 pts) 2. Is this reaction faster or slower than the similar FC reaction starting with benzene (C6H6)? Explain why. (4 pts) 3. Explain why this reaction produces the ortho and para products (but not meta). (6 pts) Use your mechanism to help explain parts #2 and #3. Use additional drawings and words as needed. to AICI N-phenylacetamide 455 sta AHO O 00 10H СОИН 08H НИ MOHO HO HO 10
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