Chem 8a Elimination Reactions Worksheet Page 2
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2CHEM 8A
Lectures 14 & 15
SUBSITUTION AND ELIMINATION REACTIONS:
S
1 vs. S
2 vs. E1 vs. E2 vs. NR
N
N
Below are reactions of alkyl halides with nucleophiles and/or bases. Some reactions will give
only one product; others will give a mixture. Recall the specific conditions required for one
reaction mechanism to be favored (except for E1).
S
1 – tertiary alkyl halide
E1 – (always a mixture with Substitution)
N
S
2 – methyl alkyl halide
E2 – potassium tert-butoxide, KOt-Bu, KOC(CH
)
N
3
3
If any one of those conditions is not met (for example, a secondary alkyl halide), determine
whether the reagent is a nucleophile (substitution), base (elimination), or both.
Look out for non-leaving groups!
NaCl
(1)
I
Acetone
F
KOt-Bu
(2)
t-BuOH
Br
CH
OH
3
(3)
Br
NaOCH
3
(4)
CH
OH
3
I
KOt-Bu
(5)
t-BuOH
HBr
(6)
I
NaCl
(7)
CH
I
3
Acetone
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