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%

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%

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Question

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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