Question 1

Which of the following statements best explains why benzene does not undergo addition reactions typical of alkenes, but instead undergoes electrophilic aromatic substitution?

Accepted Answer

Benzene is less reactive than alkenes due to its aromaticity, which would be disrupted by addition reactions.

Question 2

What is the major product when benzene reacts with bromine ($$\mathrm{Br_2$}) in $$the presence of iron(III) bromide ($$\mathrm{$$FeBr_3$$}$$)?

Accepted Answer

Bromobenzene

Question 3

Which of the following substituents on a benzene ring is an ortho/para-directing activator?

Accepted Answer

$$\mathrm{-$$OCH_3$$}$$

Question 4

A student wants to synthesize 4-nitroacetophenone from benzene. Which sequence of reactions would be most efficient?

Accepted Answer

Friedel-Crafts acylation with acetyl chloride, then nitration

Question 5

Which of the following is the correct IUPAC name for the compound with the structure $$\mathrm{CH_2$=CHCH_2CH_3}$$?

Accepted Answer

1-Butene

Question 6

When 2-methyl-2-butene reacts with $$\mathrm{HBr}$$, which carbocation intermediate is formed, and what is the major product?

Accepted Answer

A tertiary carbocation; 2-bromo-2-methylbutane

Question 7

Which reagent would convert 1-butyne to trans-2-butene?

Accepted Answer

$$\mathrm{Na/NH_3$} ($$sodium in liquid ammonia)

Question 8

Which of the following statements about the reaction of an alkene with $$\mathrm{BH_3$}$$ followed by $$\mathrm{H_2O_2, OH^-} is $$correct?

Accepted Answer

The reaction gives an anti-Markovnikov alcohol with syn addition.

Question 9

Which of the following is the correct product when 2-methyl-2-propanol is treated with concentrated $$\mathrm{H_2SO_4}$$ and heated?

Accepted Answer

Isobutylene ($$\mathrm{2-methylpropene})$$

Question 10

Which of the following statements best describes the reactivity of aldehydes compared to ketones toward nucleophilic addition?

Accepted Answer

Aldehydes are more reactive due to less steric hindrance and greater partial positive charge on the carbonyl carbon.

Question 11

Which of the following is the correct IUPAC name for the compound $$\mathrm{CH_3CH_2OCH_2CH_3}$$?

Accepted Answer

Ethoxyethane

Question 12

Which of the following reagents can be used to oxidize a primary alcohol to a carboxylic acid?

Accepted Answer

$$\mathrm{K_2Cr_2O_7} in$$ $$\mathrm{H_2SO_4}$$

Question 13

Which of the following statements about the Hofmann elimination is correct?

Accepted Answer

It produces the least substituted alkene as the major product.

Question 14

Which of the following best describes the product of the reaction between an aldehyde and a primary amine under acidic conditions?

Accepted Answer

An imine

Question 15

Which of the following is a correct statement about the basicity of amines?

Accepted Answer

Amines are more basic than amides due to the availability of the lone pair on nitrogen.

Question 16

Which of the following is the correct product when ethylene oxide (an epoxide) is treated with aqueous acid?

Accepted Answer

Ethylene glycol ($$\mathrm{HOCH_2CH_2OH})$$

Question 17

Which of the following best describes the mechanism of the Friedel-Crafts alkylation of benzene?

Accepted Answer

Generation of a carbocation electrophile, followed by its attack on the benzene ring

Question 18

Which of the following is the correct product when 2-butanol is treated with $$\mathrm{$$PBr_3$$}$$?

Accepted Answer

2-Bromobutane

Question 19

Which of the following statements about nucleophilic aromatic substitution (NAS) is correct?

Accepted Answer

NAS is favored when strong electron-withdrawing groups are ortho or para to the leaving group.

Question 20

Which of the following is the correct product when cyclohexene is treated with ozone ($$\mathrm{O_3$}) $$followed by zinc and acetic acid?

Accepted Answer

Adipaldehyde ($$\mathrm{OHC(CH_2$)_4CHO})$$

Comprehensive Study Guide: Aromatic Compounds, Alkenes, Alkynes, Alcohols, Ethers, Aldehydes, Ketones, and Amines

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