Review Of Organic Chemistry Page 12
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34Organic Chemistry I Review: Highlights of Key Reactions, Mechanisms, and Principles
12
Summary of Alkene Reactions, Ch. 8.
Memorize Reaction, Orientation where Appropriate, Stereochemistry where
Appropriate, and Mechanism where Appropriate.
-all are drawn using 1-methylcyclohexene as a prototype alkene, because both orientation and
stereochemistry effects are readily apparent.
Orientation
Stereo
Mechanism
1
HBr
Br
Markovnikov
None
Be able to
draw
(no peroxides)
completely
2
CH
3
HBr
H
Anti-Markovnikov Nonselective.
Be able to
Both cis
draw
peroxides
Br
and trans
propagation
both cis and trans
steps.
3
CH
3
+
H
O, H
OH
Markovnikov
None
Be able to
2
draw
completely
4
CH
1. Hg(OAc)
, H
O
3
2
2
OH
Markovnikov
None
Not
responsible
2. NaBH4
5
CH
3
1. BH
•THF
3
H
Anti-Markovnikov Cis
Not
responsible
2. H
O
, NaOH
OH
2
2
6
CH
1. Hg(OAc)
, ROH
3
2
OR
Markovnikov
None
Not
responsible
2. NaBH4
7
CH
3
H
, Pt
H
2
None
Cis
Not
responsible
H
D
D
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