Reactions And Synthesis Of Alkenes Worksheet - Chapter 8

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Chapter 8 Homework—Alkenes: Reactions and Synthesis
SHORT ANSWER
Section 8-1
To answer the question(s) below consider the following reaction:
When cyclohexene reacts with chlorine in carbon tetrachloride the trans-dihalide is formed.
1.
Refer to Section 8-1. Write the complete stepwise mechanism for this reaction. Be sure to
show all intermediate structures and all electron flow using arrows.
ANS:
2.
Refer to Section 8-1. Since the two chlorine atoms add to opposite faces of the cyclohexene
double bond, we say that the reaction occurs with:
a.
syn stereochemistry
b. cis stereochemistry
c.
anti stereochemistry
d. retention of stereochemistry
ANS:
c
3.
Refer to Section 8-1. The observed stereochemistry of addition of chlorine to cyclohexene is
explained by the intermediacy of a:
a.
cyclonium ion
b. carbocation
c.
carbene
d. chloronium ion
ANS:
d
1

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