Deck 4: Alcohols and Alkyl Halides: Introduction to Reaction Mechanisms

Question 1

What is the IUPAC name of the compound below?

A) 8-chloro-4-isopropyl-4,7-dimethylnonane
B) 2-chloro-6-isopropyl-3,6-dimethylnonane
C) 2-chloro-3,6,7-trimethyl-6-propyloctane
D) 6-sec-butyl-2-chloro-3,6-dimethyloctane

Answer 1

2-chloro-6-isopropyl-3,6-dimethylnonane

Question 2

Chlorination of pentane gives a mixture of isomers having the molecular formula $\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{Cl}$ . The percentage of 1 -chloropentane is $22 \%$ . Assuming the secondary hydrogens in pentane are equally reactive to monochlorination, what is the percentage of 3-chloropentane in the mixture?

A) $48 \%$
B) $26 \%$
C) $22 \%$
D) $14 \%$

Answer 2

$26 \%$

Question 3

Which one of the following gives a single monochlorination product?

A) 2,2-dimethylpropane
B) 2,2-dimethylbutane
C) 2,3-dimethylbutane
D) 2-methylpropane

Answer 3

2,2-dimethylpropane

Question 4

What are the products of the following reaction?

A) 1-bromobutane and water
B) 1-bromobutane and hydrogen
C) butane and $\mathrm{HOBr}$
D) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OBr}+$ hydrogen

Question 5

Arrange the following alcohols in order of their decreasing reactivity with $\mathrm{HBr}$ (most reactive first).

A) I $>$ II $>$ III
B) I $>$ III $>$ II
C) III $>$ I $>$ II
D) II $>$ III $>$ I

Question 6

Arrange the following carbocations in order of their decreasing stabilities (most stable first).

A) I $>$ II $>$ III
B) III $>$ II $>$ I
C) I $>$ III $>$ II
D) II $>$ III $>$ I

Question 7

Which of the following is the most stable radical?

A)

B)

C)

D)

Question 8

The central carbon of the tert-butyl carbocation, $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}^{+}$ , is

A) $\mathrm{sp}^{2}$ hybridized with $\mathrm{a}+1$ formal charge.
B) $\mathrm{sp}^{2}$ hybridized with a 0 formal charge.
C) $\mathrm{sp}^{3}$ hybridized with $\mathrm{a}+1$ formal charge.
D) $\mathrm{sp}^{3}$ hybridized with a 0 formal charge.

Question 9

Dibromination of isopropylcyclopentane gives a product which can be isolated in good yields. Which of the following would you predict to be this product?

A) A
B) B
C) C
D) D

Question 10

Which of the following mechanistically depicts the protonation of tert-butyl alcohol by hydrogen bromide?

A)

B)

C)

D)

Question 11

If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of $\mathrm{HCl}$ , what major product would you expect?

A)
B)

C)

D) there is no way to know