ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Chapter 10, Problem 12PP

Practice Problem 10.12

Benzylic radicals, due to the adjacent benzene ring, have even greater possibility for delocalization than allylic radicals. Draw contributing resonance structures that show this delocalization for the benzylic radical derived from methyl benzene. (Hint: There are four contributing resonance structures for this benzylic radical.)

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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%
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