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 I. Short Answer (24 pts total) 1. For each molecule or ion circle the appropriate letter to indicate if the structure is Aromatic (A), Anti-Aromatic (AA) or Neither (N) aromatic or anti-aromatic. (1 pt each, 4 pts total) A AAN (circle one) A AAN (circle one) A AAN (circle one) A AAN (circle one) 2. Rank the following molecules from #1 (fastest) to #3 (slowest) in their reaction with Cl₂ / FeCl3. (6 pts) Br NCH3 H II. Conside 1-chlo 1. Dr 2. Is 3. Explain why pyrrole is a much WEAKER base than pyridine (pK,'s for their conjugate acids shown to right) (6 pts) H... HOH Pyrrole Pyridine pKa = -4 pKa = +5 4. Explain the differences in pK, (vs benzoic acid) of these substituted benzoic acids based on fundamental chemical principles (not just what pK, means). (8 pts) OH .OH OH PK, 4.20 OCH3 4.47 3.70 3.
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 I. Short Answer (24 pts total) 1. For each molecule or ion circle the appropriate letter to indicate if the structure is Aromatic (A), Anti-Aromatic (AA) or Neither (N) aromatic or anti-aromatic. (1 pt each, 4 pts total) A AAN (circle one) A AAN (circle one) A AAN (circle one) A AAN (circle one) 2. Rank the following molecules from #1 (fastest) to #3 (slowest) in their reaction with Cl₂ / FeCl3. (6 pts) Br NCH3 H II. Conside 1-chlo 1. Dr 2. Is 3. Explain why pyrrole is a much WEAKER base than pyridine (pK,'s for their conjugate acids shown to right) (6 pts) H... HOH Pyrrole Pyridine pKa = -4 pKa = +5 4. Explain the differences in pK, (vs benzoic acid) of these substituted benzoic acids based on fundamental chemical principles (not just what pK, means). (8 pts) OH .OH OH PK, 4.20 OCH3 4.47 3.70 3.
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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Question
Plz draw out a detailed mechanism for the ortho product !
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
Transcribed Image Text:I. Short Answer (24 pts total)
1. For each molecule or ion circle the appropriate letter to indicate if the structure is Aromatic (A),
Anti-Aromatic (AA) or Neither (N) aromatic or anti-aromatic. (1 pt each, 4 pts total)
A AAN
(circle one)
A AAN
(circle one)
A AAN
(circle one)
A AAN
(circle one)
2. Rank the following molecules from #1 (fastest) to #3 (slowest) in their reaction with Cl₂ / FeCl3. (6 pts)
Br
NCH3
H
II. Conside
1-chlo
1. Dr
2. Is
3. Explain why pyrrole is a much WEAKER base than pyridine (pK,'s for their conjugate acids shown to right) (6 pts)
H...
HOH
Pyrrole Pyridine
pKa = -4
pKa = +5
4. Explain the differences in pK, (vs benzoic acid) of these substituted benzoic acids based on fundamental chemical
principles (not just what pK, means). (8 pts)
OH
.OH
OH
PK,
4.20
OCH3
4.47
3.70
3.
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