Question 1

Which of the following statements best describes Markovnikov's rule in the addition of HX to an alkene?

Accepted Answer

The hydrogen adds to the carbon atom of the double bond with the greater number of hydrogen atoms.

Question 2

Which of the following acids is the strongest Brønsted acid?

Accepted Answer

$\mathrm{HCl}$ (hydrochloric acid)

Question 3

What is the product of the reaction between 1-butene and $\mathrm{Br_2}$ in $\mathrm{CCl_4}$?

Accepted Answer

1,2-dibromobutane

Question 4

Which of the following best explains why carbocation rearrangements (such as hydride or alkyl shifts) occur during addition reactions?

Accepted Answer

To form a more stable carbocation intermediate.

Question 5

Which of the following solvents would most likely increase the nucleophilicity of $\mathrm{Cl^-}$ in an alkene addition reaction?

Accepted Answer

$\mathrm{CCl_4}$

Question 6

In the reaction of cyclohexene with $\mathrm{Br_2}$ in water, what is the major product?

Accepted Answer

trans-1-bromo-2-hydroxycyclohexane

Question 7

Which of the following statements about the oxidation of alkenes with $\mathrm{OsO_4}$ is correct?

Accepted Answer

It produces a vicinal diol via syn addition.

Question 8

Which of the following is the correct formula for calculating the index of hydrogen deficiency (IHD) for a compound?

Accepted Answer

$\mathrm{IHD = \frac{2C + 2 - H}{2}}$

Question 9

Which of the following best describes the stereochemistry of the addition of $\mathrm{Br_2}$ to an alkene?

Accepted Answer

Anti addition via a bridged bromonium ion intermediate.

Question 10

Which of the following is a correct statement about Lewis acids and bases?

Accepted Answer

Lewis acids are electron pair acceptors.

Question 11

A student reacts 2-methyl-2-butene with $\mathrm{HBr}$. Which major product is expected, considering carbocation rearrangement?

Accepted Answer

2-bromo-2-methylbutane

Question 12

Which of the following is the correct order of carbocation stability?

Accepted Answer

tertiary > secondary > primary

Question 13

Which reagent would you use to convert an alkene to a vicinal diol via syn addition?

Accepted Answer

$\mathrm{OsO_4}$

Question 14

Which of the following is true about the addition of $\mathrm{H_2O}$ to an alkene in the presence of acid?

Accepted Answer

The reaction proceeds via a carbocation intermediate and follows Markovnikov's rule.

Question 15

Which of the following is the product of ozonolysis of 1-hexene followed by reductive workup?

Accepted Answer

Propanal and butanal

Question 16

Which of the following is a characteristic of anti addition in alkene reactions?

Accepted Answer

Addition of substituents to opposite faces of the double bond.

Question 17

Which of the following is the correct product of hydroboration-oxidation of 1-methylcyclopentene?

Accepted Answer

1-methylcyclopentanol

Question 18

Which of the following is the correct description of the role of $\mathrm{Hg(OAc)_2}$ in oxymercuration-demercuration?

Accepted Answer

It forms a mercurinium ion intermediate, preventing carbocation rearrangement.

Question 19

Which of the following is the correct product of the reaction of 1-hexene with $\mathrm{Br_2}$ in $\mathrm{CCl_4}$?

Accepted Answer

1,2-dibromohexane

Organic Chemistry Study Notes: Acids, Bases, Alkenes, and Alkene Reactions

Study Guide - Practice Questions