Question 1

Which reagent is required to convert 2-methyl-2-butene to 2-bromo-2-methylbutane as shown below?

$$\mathrm{\ce{CH2=C(CH3)-CH2-CH3}} \longrightarrow \mathrm{\ce{CH3-C(Br)(CH3)-CH2-CH3}}$$

Accepted Answer

Aqueous $$\mathrm{HBr}$$

Question 2

What is the major product of the reaction between 2-methyl-2-butene and aqueous $$\mathrm{HBr}$$?

$$\mathrm{\ce{CH2=C(CH3)-CH2-CH3}} + \mathrm{HBr} \longrightarrow$$

Accepted Answer

$$\mathrm{\ce{CH3-C(Br)(CH3)-CH2-CH3}}$$

Question 3

Which mechanism best describes the addition of $$\mathrm{HBr} to 2-$$methyl-2-butene in aqueous solution?

Accepted Answer

Electrophilic addition via Markovnikov rule

Question 4

In the reaction of 2-methyl-2-butene with $$\mathrm{HBr}$$, which intermediate is formed?

Accepted Answer

A tertiary carbocation

Question 5

What is the first step in the mechanism for the reaction of 2-methyl-2-butene with $$\mathrm{HBr}$$?

Accepted Answer

Protonation of the alkene to form a carbocation

Question 6

What is the product of the reaction between 1-methylcyclopentene and $$\mathrm{CH_3CO_3H}$$ followed by hydrolysis with $$\mathrm{H_2O}$$?

Accepted Answer

trans-1-methyl-1,2-cyclopentanediol

Question 7

Which type of reaction mechanism is involved in the conversion of 1-methylcyclopentene to a diol using $$\mathrm{CH_3CO_3H}$$ and $$\mathrm{H_2O}$$?

Accepted Answer

Epoxidation followed by acid-catalyzed ring opening

Question 8

What is the intermediate formed when 1-methylcyclopentene reacts with $$\mathrm{CH_3CO_3H}$$?

Accepted Answer

An epoxide

Question 9

Which statement best explains the stereochemistry of the diol formed from 1-methylcyclopentene via epoxidation and hydrolysis?

Accepted Answer

The diol is formed via anti addition, resulting in a trans product.

Question 10

Which of the following best describes the role of $$\mathrm{CH_3CO_3H} in $$the reaction with 1-methylcyclopentene?

Accepted Answer

It acts as an oxidizing agent to form an epoxide.

Question 11

If the reaction of 1-methylcyclopentene with $$\mathrm{CH_3CO_3H}$$ and $$\mathrm{H_2O} is $$performed in $$\mathrm{D_2O}$$ instead of $$\mathrm{H_2O}$$, what is the expected product?

Accepted Answer

trans-1-methyl-1,2-cyclopentanediol-d2

Question 12

Which of the following is a common misconception about the reaction of alkenes with peroxyacids followed by hydrolysis?

Accepted Answer

The reaction proceeds via a carbocation intermediate.

Organic Chemistry Reaction Mechanisms: Bromination and Epoxidation

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