Practice Exercises

Question 1 Question 2
Organic CHEMISTRY

What is the major product of the dehydration of
2-methylcyclohexanol?
A) 1-methylcyclohexene
B) 2-methylcyclohexene
C) 3-methylcyclohexene
Of the isomeric alcohols having the molecular
formula C5H12O, which one will undergo acid-
catalyzed dehydration most readily?
A) 2-pentanol
B) 2-methyl-1-butanol

D) cyclohexene C) 2-methyl-2-butanol

D) 3-methyl-2-butanol

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 Practice Exercises
Question 3 Question 4
Organic CHEMISTRY

Which would react with KOCH2CH3 in ethanol Which would react with KOC(CH3)3/(CH3)3COH
faster? faster?

A) cis-2-tert-butylcyclohexyl bromide A) cis-3-tert-butylcyclohexyl bromide

B) trans-2-tert-butylcyclohexyl bromide B) trans-3-tert-butylcyclohexyl bromide

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 Practice Exercises
Question 5 Question 6
Organic CHEMISTRY

Which reaction would be most likely to proceed Which one of the following best describes a
by an E1 mechanism? mechanistic feature of the reaction of 3-
bromopentane with sodium ethoxide?
A) 2-chloro-2-methylbutane + NaOCH2CH3 A) The reaction occurs in a single step
in ethanol (heat) which is bimolecular.

B) 1-bromo-2-methylbutane + KOC(CH3)3 B) The reaction occurs in two steps, both of

in DMSO which are unimolecular.
C) The rate-determining step involves the
C) 2-bromo-2-methylbutane in ethanol
formation of carbocation (CH3CH2)2CH+.
(heat)
D) The carbon-halogen bond breaks fast
D) 2-methyl-2-butanol + KOH
and the rate-determining step follows.
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 Practice Exercises
Question 7 Question 8
Organic CHEMISTRY

3-Bromo-3-methylpentane reacts with sodium Which one of the following alkyl halides would be
ethoxide in ethanol by this mechanism: expected to give the highest ratio of
substitution to elimination on treatment with
sodium ethoxide in ethanol (50oC)?
A) S N1
A) 1-bromopentane
B) SN2
B) 2-bromopentane
C) E1
C) 3-bromopentane
D) E2
D) 2-bromo-3-methylbutane

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Question 9 Question 10
Organic CHEMISTRY

Give the product (or products) that you would Give the product (or products) that you would
expect to be formed in the following reaction. expect to be formed in the following reaction.

Predict and draw the mechanism/s (SN1, SN2, E1 Predict and draw the mechanism/s (SN1, SN2, E1
or E2) by which the product/s is/are formed or E2) by which the product/s is/are formed
and give the relative amount of each (i.e., only and give the relative amount of each (i.e., only
reaction product, major or minor product). reaction product, major or minor product).

- 50oC 25oC
CH3CH2CH2Br + CH3O (CH3CH2)3CBr
CH3OH CH3OH

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