Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 6, Problem 47P
1-Bromo[2.2.1] bicycloheptane is unreactive toward both
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The compound below is treated with chlorine in the presence of light.
CH-CH3
Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond.
. You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms.
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?
Both bicyclo[3.3.1]nonane and bicyclo[2.2.1]heptane are saturated hydrocarbons composed of only 2° and 3° carbons.
Recall that radical substitution generally takes place preferentially at a 3° carbon. Indeed, when bicyclo[3.3.1]nonane is
treated with bromotrichloromethane under irradiation, substitution takes place 100% at the 3° carbon. Under the same
conditions, however, no substitution is observed at the 3° carbon in bicyclo[2.2.1]heptane. Explain. Hint: Build molecular
models of each of these compounds.
BrCCl.
hv
hv
Br
Br
Bicyclo[3.3.1]nonane
100%
Bicyclo[2.2.1]heptane
0%
Chapter 6 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
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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