Question 1

Which of the following statements best describes Markovnikov's Rule as it applies to the addition of HX to an alkene?

Accepted Answer

The hydrogen atom adds to the carbon with the most hydrogens already attached.

Question 2

Which of the following is the correct electron-pushing mechanism for the hydration of an alkene under acidic conditions?

Accepted Answer

Protonation of the alkene to form a carbocation, followed by nucleophilic attack by water, then deprotonation.

Question 3

Which of the following best explains why tert-butyl carbocations are more stable than methyl carbocations?

Accepted Answer

Tert-butyl carbocations are stabilized by hyperconjugation and inductive effects from three alkyl groups.

Question 4

Which product is expected from the reaction of 1-butene with Br$$_2 in $$water?

Accepted Answer

1-Bromo-2-butanol

Question 5

Which of the following is a correct statement about the Diels-Alder reaction?

Accepted Answer

It is a [4+2] cycloaddition reaction between a conjugated diene and a dienophile.

Question 6

Which of the following substituents is an activator for electrophilic aromatic substitution (EAS) reactions?

Accepted Answer

$$-\mathrm{OH}$$

Question 7

In the nitration of benzene, what is the electrophile that reacts with the aromatic ring?

Accepted Answer

$$\mathrm{NO}_2^+ ($$nitronium ion)

Question 8

Which of the following best describes the product of ozonolysis of 1-methylcyclohexene followed by reductive workup (Zn/AcOH)?

Accepted Answer

A cyclohexanone and acetaldehyde

Question 9

Which of the following statements about the Wittig reaction is correct?

Accepted Answer

It converts a carbonyl compound into an alkene using a phosphonium ylide.

Question 10

Which of the following is the major product when benzene reacts with methyl chloride ($$\mathrm{CH}_3\mathrm{Cl}) $$and AlCl$$_3$$?

Accepted Answer

Toluene

Question 11

Which of the following best describes the mechanism of the Claisen condensation?

Accepted Answer

A nucleophilic enolate attacks an ester, forming a $$\beta-$$keto ester.

Question 12

Which of the following is a correct statement about the effect of electron-withdrawing groups on the rate of electrophilic aromatic substitution?

Accepted Answer

They decrease the rate by destabilizing the arenium ion intermediate.

Question 13

Which of the following is the correct product of the reaction between 1-butyne and excess $$\mathrm{HBr}$$?

Accepted Answer

2,2-Dibromobutane

Question 14

Which of the following best describes the outcome of the Birch reduction of benzene?

Accepted Answer

Formation of 1,4-cyclohexadiene

Question 15

Which of the following is the correct order of reactivity for nucleophilic aromatic substitution (from most to least reactive)?

Accepted Answer

Nitrobenzene \u003e Chlorobenzene \u003e Toluene

Question 16

Which of the following is the correct product of the reaction of 2-methyl-2-butene with $$\mathrm{O}_3$$ followed by $$\mathrm{Zn}/\mathrm{AcOH}$$?

Accepted Answer

Acetone and propanal

Question 17

Which of the following best describes the effect of an $$-\mathrm{NO}_2$$ group at the para position on the reactivity of benzene toward EAS?

Accepted Answer

It deactivates the ring and directs new substituents to the meta position.

Question 18

Which of the following is the correct product of the reaction of benzene with acetyl chloride ($$\mathrm{CH}_3\mathrm{COCl}) $$and AlCl$$_3$$?

Accepted Answer

Acetophenone

Question 19

Which of the following best describes the mechanism of the aldol reaction under basic conditions?

Accepted Answer

Enolate ion attacks a carbonyl carbon, forming a $$\beta-$$hydroxy carbonyl compound.

Organic Chemistry: Nucleophilic Reactions, Aromaticity, and Radical Chemistry Study Guide

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