Consider the reaction scheme below NBS hv a. Draw the major regioisomer resulting from monobromination of cyclohexene with N-bromosuccinimide. If this major regioisomer is produced as a mixture of stereoisomers, draw each stereoisomer and indicate the relative amount of each stereoisomer (That is, if one stereoisomer is formed preferentially label it is as "major." If both are formed in equal amounts label each as "50%"). b. Draw an arrow pushing reaction mechanism for this reaction. You should draw an initiation step, two propagation steps, and two possible termination steps for the radical chain reaction and clearly label which step is which. Your mechanism can use Br2 as the source of bromine radicals in the initiation step that will be present as a minor, low concentration impurity in the NBS.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 46CTQ
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1. Consider the reaction scheme below
NBS
hv
a. Draw the major regioisomer resulting from monobromination of
cyclohexene with N-bromosuccinimide. If this major regioisomer is
produced as a mixture of stereoisomers, draw each stereoisomer and
indicate the relative amount of each stereoisomer (That is, if one
stereoisomer is formed preferentially label it is as "major." If both are formed
in equal amounts label each as "50%").
b. Draw an arrow pushing reaction mechanism for this reaction. You should
draw an initiation step, two propagation steps, and two possible termination
steps for the radical chain reaction and clearly label which step is which.
Your mechanism can use Br2 as the source of bromine radicals in the
initiation step that will be present as a minor, low concentration impurity in
the NBS.
36°F
Transcribed Image Text:1. Consider the reaction scheme below NBS hv a. Draw the major regioisomer resulting from monobromination of cyclohexene with N-bromosuccinimide. If this major regioisomer is produced as a mixture of stereoisomers, draw each stereoisomer and indicate the relative amount of each stereoisomer (That is, if one stereoisomer is formed preferentially label it is as "major." If both are formed in equal amounts label each as "50%"). b. Draw an arrow pushing reaction mechanism for this reaction. You should draw an initiation step, two propagation steps, and two possible termination steps for the radical chain reaction and clearly label which step is which. Your mechanism can use Br2 as the source of bromine radicals in the initiation step that will be present as a minor, low concentration impurity in the NBS. 36°F
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