Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 15.6, Problem 15.8P
When Br2 is added to buta-1,3-diene at −15 °C, the product mixture contains 60% of product A and 40% of product B. When the same reaction takes place at 60 °C, the product ratio is 10% A and 90% B.
- a. Propose structures for products A and B. (Hint: In many cases, an allylic carbocation is more stable than a bromonium ion.)
- b. Propose a mechanism to account for formation of both A and B.
- c. Show why A predominates at −15 °C and B predominates at 60 °C.
- d. If you had a solution of pure A, and its temperature were raised to 60 °C, what would you expect to happen? Propose a mechanism to support your prediction.
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What is the relationship between A and B?
H3C
A
Br
Cl
H3C
B
Br
relationship
(check all that apply)
O same molecule
O enantiomer
O diastereomer
structural isomer
O stereoisomer
isomer
O need more information to decide
O same molecule
☐ enantiomer
Br
Br
Br
CH3
Br
CI
CH3
O diastereomer
☐ structural isomer
☐ stereoisomer
isomer
O need more information to decide
O same molecule
O enantiomer
Odiastereomer
structural isomer
O stereoisomer
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O need more information to decide
b. Please complete the zig-zag conformation of the compound
(3R,4S)-3,4-dichloro-2,5-dimethylhexane by writing the respective atoms in the boxes.
4
c. Serricornin, the female-produced sex pheromone of the cigarette beetle, has the following structure.
OH
What is the maximum number of possible stereoisomers?
Is this structure a meso compound?
d. Please consider the natural product alkaloids shown below.
Are these two structures enantiomers, diastereomers or conformers?
H
HO
H
H
HN
HO
HN
R
R
с
R=H
cinchonidine
R=ET
cinchonine
H
Chapter 15 Solutions
Organic Chemistry (9th Edition)
Ch. 15.2 - Prob. 15.1PCh. 15.2 - Prob. 15.2PCh. 15.2 - Prob. 15.3PCh. 15.4 - Prob. 15.4PCh. 15.4 - Prob. 15.5PCh. 15.5 - Treatment of an alkyl halide with AgNO3 in alcohol...Ch. 15.5 - Propose a mechanism for each reaction, showing...Ch. 15.6 - When Br2 is added to buta-1,3-diene at 15 C, the...Ch. 15.7 - Prob. 15.9PCh. 15.7 - When N-bromosuccinimide is added to hex-1-ene in...
Ch. 15.7 - Prob. 15.11PCh. 15.9 - Addition of 1-bromobut-2-ene to magnesium metal in...Ch. 15.10 - Show how you might synthesize the following...Ch. 15.11 - Predict the products of the following proposed...Ch. 15.11 - Prob. 15.15PCh. 15.11A - Prob. 15.16PCh. 15.11B - Prob. 15.17PCh. 15.11B - Predict the products of the following Diels-Alder...Ch. 15.12C - Prob. 15.19PCh. 15.12C - Prob. 15.20PCh. 15.13C - Prob. 15.21PCh. 15.13D - Using the examples in Table15-2 to guide you,...Ch. 15.14 - Phenolphthalein is an acid-base indicator that is...Ch. 15 - Prob. 15.24SPCh. 15 - Prob. 15.25SPCh. 15 - Show how the reaction of an allylic halide with a...Ch. 15 - Prob. 15.27SPCh. 15 - A solution was prepared using 0.0010 g of an...Ch. 15 - Prob. 15.29SPCh. 15 - Prob. 15.30SPCh. 15 - Prob. 15.31SPCh. 15 - Prob. 15.32SPCh. 15 - Prob. 15.33SPCh. 15 - Give the structures of the products represented by...Ch. 15 - Furan and malemide undergo a Diels-Alder reaction...Ch. 15 - Prob. 15.36SPCh. 15 - Prob. 15.37SPCh. 15 - Prob. 15.38SPCh. 15 - Prob. 15.39SPCh. 15 - Determine whether each structure is likely to be...Ch. 15 - An important variation of the Diels-Alder reaction...
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