Elimination Reactions And Alkene Synthesis - Organic Chemistry Worksheet With Answers Page 2

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9) What major product results when 2-bromo-2-methylbutane is treated with sodium ethoxide.
10) How many distinct alkenes can result from E2 elimination of the compound below? Give their
structures and IUPAC names.
I
CH
3
11) Give the major product and the mechanism of the following reaction.
H
C
H
3
NaOCH
3
Ph
Ph
CH
OH
3
Br
12) Predict the most likely mechanism and the product for the reaction below.
NaOCH
3
CH
OH
H
C
3
3
H
C
3
Cl
13) Predict the most likely mechanism and the product from the reaction between
2-chloro-2-methylpentane and sodium ethoxide in ethanol.
14) The major product which results when 2-chloro-2-methylpentane is heated in ethanol is an
ether. Show and name the mechanism by which this ether forms.
15) Which of the following mechanisms feature carbocation intermediates?
A) S N 1 only
B) S N 2 only
C) E1 only
D) E2 only
E) both S N 1 and E1
16) Which mechanism(s) give(s) alkenes as the major products, Sn1, Sn2, E1, or E2?
17) Which compound produces only one alkene when treated with sodium methoxide?
A) 2-chloro-2-methylpentane
B) 3-chloro-3-ethylpentane
C) 3-chloro-2-methylpentane
D) 2-chloro-4-methylpentane
E) 2-chloro-3-ethylpentane
18) When 3-iodo-3-ethylpentane is treated with sodium methoxide in methanol, the major
organic product is an ______ that is generated through an ______ mechanism.
A) ether, S N 1
B) ether, S N 2
C) ether, E1
D) alkene, E2
E) alkene, E1

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