Problem Set 11 (Answer Key)
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CHEM 2320 1 Problem Set 11: Chapter 11 Instructions: Working with your assigned group, answer each of the questions below. If necessary, you may include answers on extra sheets of paper. This assignment is due by January 2
5
th
, 202
4
. For students
at distance campuses: please scan your completed problem sets as pdf files and email them to m.christiansen@usu.edu by the due date. The answer key will be posted the day after. Late problem sets will be
docked by 50 percent. Each question is worth 0.5 points (10 points for the assignment). You may use any material
(your book, instructor, notes, the Internet, your classmates, etc.) you wish to complete this assignment. Where
applicable, you must show your work for full credit
.
11.1. How to Determine Aromaticity 1.
Question 11.11
Identify the following compounds as aromatic, non-aromatic, or anti-aromatic (the order of options in the answer
choices correspond to the left-to-right order of the compounds).
A.
Aromatic; Aromatic
B.
Aromatic; Non-aromatic
C.
Non-aromatic; Non-aromatic
D.
Anti-aromatic; Non-aromatic
E.
Non-aromatic; Anti-aromatic
Answer: A Click here for a video explanation: https://www.youtube.com/watch?v=x7J20TBYSMc&feature=youtu.be
2.
Question 11.13
Identify each of the following compounds as aromatic, non-aromatic, or anti-aromatic (the order of options in
the answer choices correspond to the left-to-right order of the compounds).
A.
Anti-aromatic; Aromatic
B.
Aromatic; Non-aromatic
C.
Non-aromatic; Non-aromatic
D.
Anti-aromatic; Non-aromatic
E.
Anti-aromatic; Anti-aromatic
Answer: D Click here for a video explanation: https://www.youtube.com/watch?v=v-SMEUN80iA&feature=youtu.be
CHEM 2320 2 3. Question 11.14 Identify each of the following compounds as aromatic, non-aromatic, or anti-aromatic (the order of options in the answer choices correspond to the left-to-right order of the compounds). A. Non-aromatic; Anti-aromatic; Anti-aromatic B. Anti-aromatic; Aromatic; Non-aromatic C. Anti-aromatic; Aromatic; Anti-aromatic D. Non-aromatic; Anti-aromatic; Non-aromatic E. Non-aromatic; Anti-aromatic; Aromatic Answer: E Click here for a video explanation: https://www.youtube.com/watch?v=EUTRu5q-eTw&feature=youtu.be
4. Question 11.15 Identify each of the following compounds as aromatic, non-aromatic, or anti-aromatic (the order of options in the answer choices correspond to the left-to-right order of the compounds). A. Non-aromatic; Aromatic; Aromatic; Anti-aromatic B. Non-aromatic; Non-aromatic; Anti-aromatic; Anti-aromatic C. Non-aromatic; Aromatic; Anti-aromatic; Aromatic D. Aromatic; Aromatic; Anti-aromatic; Anti-aromatic E. Non-aromatic; Aromatic; Anti-aromatic; Anti-aromatic Answer: C Click here for a video explanation: https://www.youtube.com/watch?v=ub-YQKDATcE&feature=youtu.be
5. In which of the following compounds is the nitrogen’s lone pair in a p
-orbital?
(Hint: the correct answer(s) have N atoms whose lone pairs DO resonance-delocalize into adjacent double bonds. If needed, please review Sections 11.1 and 2.5 of our Tophat text.)
Answer: A
A. I B. II C. I and II D. None of the above
CHEM 2320 3 11.2. Effects of Aromaticity 6. Question 11.3 Which of the following molecules will undergo an SN1 reaction more quickly? Why? A. I because it forms an aromatic carbocation. B. II because it forms an aromatic carbocation. C. Both I and II are equally reactive in an S
N
1
reaction. D. I because it forms an anti-aromatic carbocation. E. II because it forms an anti-aromatic carbocation. Answer: B Click here for a video explanation: https://www.youtube.com/watch?v=ZGtj1guad8E&feature=youtu.be 7. Question 11.4 Which of the following molecules will be more acidic and why? A. I because it forms an aromatic conjugate base. B. II because it forms an aromatic conjugate base. C. Both I and II are equally acidic. D. I because it forms an anti-aromatic conjugate base. E. II because it forms an anti-aromatic conjugate base. Answer: B Click here for a video explanation: https://www.youtube.com/watch?v=0XxggxEQ9gs&feature=youtu.be
CHEM 2320 4 11.3. Side Reactions of Benzenes 8. Question 11.5 Predict the product of the following reaction: Answer: C Click here for a video explanation: https://www.youtube.com/watch?v=T0yHbQna0pQ&feature=youtu.be 9. Question 11.6 Predict the product of the following reaction: Answer: A Click here for a video explanation: https://www.youtube.com/watch?v=88uy-gNrs4c&feature=youtu.be
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CH3CH2CH2CI
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