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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 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.

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter27: Amines
Section: Chapter Questions
Problem 3CTQ
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Plz draw out a detailed mechanism for the ortho product !
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
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.
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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