Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 6, Problem 47P
1-Bromo[2.2.1] bicycloheptane is unreactive toward both
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2-vinylmethylenecyclopropane rearranges in the gas phase to 3- methylenecyclopentene. Two possible mechanisms are:
a)Sketch a reaction diagram for each process
b)How might an isotopic labeling experiment distinguish between these mechanisms?
Poly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3-
dimethylcyclopentane. To accomplish their syntheses, Poly chooses to start from a trisubstituted
alkene while B-Ryan chooses to start from a disubstituted alkene isomer. Poly's synthesis
provides a mixture of isomers while B-Ryan's provides two stereoisomers. Both synthetic
approaches are shown below.
Me
Me,
Me,
.CI
Me
HCI
A
B-Ryan's
Synthesis
Me
'CI
+
75%
25%
Ме
Me
Me
Me...
Me
B
Me
C
HCI
A
Poly's
Synthesis
-Me
Ме
'CI
'CI
+
+
Me..
.CI
+
a trace mixture ;
of constitutional
D
Ме
chloroalkane
isomers
Using your mechanistic knowledge of alkene reactions:
(a) Explain the selectivity (regio and stereo) observed in B-Ryan's synthesis.
(b) Propose a mechanism that accounts the formation of isomer C in Poly's synthesis.
(c) Draw the major stereoisomer(s) formed in the "trace mixture of constitutional isomers" isolated
in Poly's synthesis.
9.
2c.
Chapter 6 Solutions
Organic Chemistry
Ch. 6 - Prob. 1PPCh. 6 - Prob. 2PPCh. 6 - Prob. 3PPCh. 6 - Prob. 4PPCh. 6 - Prob. 5PPCh. 6 - PRACTICE PROBLEM 6.6
reactions that involve...Ch. 6 - PRACTICE PROBLEM 6.7 Rank the following...Ch. 6 - Prob. 8PPCh. 6 - Prob. 9PPCh. 6 - Prob. 10PP
Ch. 6 - Prob. 11PPCh. 6 - Prob. 12PPCh. 6 - Prob. 13PPCh. 6 - Prob. 14PPCh. 6 - Prob. 15PPCh. 6 - Prob. 16PPCh. 6 - Prob. 17PPCh. 6 - Prob. 18PPCh. 6 - Prob. 19PPCh. 6 - Prob. 20PCh. 6 - Prob. 21PCh. 6 - Prob. 22PCh. 6 - Prob. 23PCh. 6 - Prob. 24PCh. 6 - Listed below are several hypothetical nucleophilic...Ch. 6 - Prob. 26PCh. 6 - 6.27 Write conformational structures for the...Ch. 6 - 6.28 Consider the reaction of with .
(a) Would...Ch. 6 - Prob. 29PCh. 6 - Prob. 30PCh. 6 - Prob. 31PCh. 6 - Prob. 32PCh. 6 - 1-Bromobicyclo[2, 2,1] heptane is extremely...Ch. 6 - When ethyl bromide reacts with potassium cyanide...Ch. 6 - Prob. 35PCh. 6 - Prob. 36PCh. 6 - When the alkyl bromides (listed here) were...Ch. 6 - Prob. 38PCh. 6 - Prob. 39PCh. 6 - Prob. 40PCh. 6 - Prob. 41PCh. 6 - 6.42 The reaction of chloroethane with water in...Ch. 6 - Prob. 43PCh. 6 - Prob. 44PCh. 6 - Prob. 45PCh. 6 - Prob. 46PCh. 6 - 1-Bromo[2.2.1] bicycloheptane is unreactive toward...Ch. 6 - Open the computer molecular model tided...Ch. 6 - Prob. 49PCh. 6 - Consider the solvolysis reaction of (1S,...Ch. 6 - 2. Consider the following sequence of reactions,...
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