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
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter27: Amines
Section: Chapter Questions
Problem 3CTQ
Question
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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