Q: A compound undergoes oxidation at the benzylic position to form benzoic acid. Which starting material is most likely?

Toluene ($$\text{C}_6\text{H}_5\text{CH}_3)$$

Q: Which spectroscopic feature is most characteristic of aromatic compounds in IR spectroscopy?

A set of absorptions near $$1600\ \text{cm}^{-1}$$ due to $$\text{C}=\text{C}$$ stretching

Q: Which reagent is required for the halogenation of benzene via electrophilic aromatic substitution?

A Lewis acid such as $$\text{FeCl}_3$$

Q: In the nitration of benzene, which species acts as the electrophile?

Nitronium ion ($$\text{NO}_2^+)$$

Q: Which substituent on a benzene ring is an ortho/para director in electrophilic aromatic substitution?

Methoxy group ($$\text{OCH}_3)$$

Question 1

Which of the following compounds is NOT aromatic according to Huckel's rule?

Accepted Answer

Cyclobutadiene

Question 2

What is the correct IUPAC name for the compound shown below?

$$	ext{A benzene ring with a methyl group at position 1 and a nitro group at position 3}$$

Accepted Answer

3-nitrotoluene

Question 3

Which of the following statements best explains the unusual stability of benzene?

Accepted Answer

Benzene's $$	ext{6} \pi$$ electrons are delocalized over the ring, lowering its energy.

Question 4

Which compound is classified as an aromatic compound other than benzene?

Accepted Answer

Pyrrole

Question 5

A compound undergoes oxidation at the benzylic position to form benzoic acid. Which starting material is most likely?

Accepted Answer

Toluene ($$	ext{C}_6	ext{H}_5	ext{CH}_3)$$

Question 6

Which spectroscopic feature is most characteristic of aromatic compounds in IR spectroscopy?

Accepted Answer

A set of absorptions near $$1600\ 	ext{cm}^{-1}$$ due to $$	ext{C}=	ext{C}$$ stretching

Question 7

During electrophilic aromatic substitution, which step is rate-determining?

Accepted Answer

Formation of the arenium ion (carbocation intermediate)

Question 8

Which reagent is required for the halogenation of benzene via electrophilic aromatic substitution?

Accepted Answer

A Lewis acid such as $$	ext{FeCl}_3$$

Question 9

In the nitration of benzene, which species acts as the electrophile?

Accepted Answer

Nitronium ion ($$	ext{NO}_2^+)$$

Question 10

Which of the following is a limitation of Friedel–Crafts alkylation?

Accepted Answer

Carbocation rearrangements can lead to unexpected products.

Question 11

Which substituent on a benzene ring is an ortho/para director in electrophilic aromatic substitution?

Accepted Answer

Methoxy group ($$	ext{OCH}_3)$$

Question 12

If a benzene ring has both a methyl group and a nitro group, which position will a new substituent most likely add to?

Accepted Answer

The position ortho to the methyl group and meta to the nitro group

Question 13

Which sequence of reactions would best synthesize p-nitrotoluene from benzene?

Accepted Answer

Friedel–Crafts alkylation with methyl chloride followed by nitration

Question 14

What is the correct IUPAC name for the following compound?

$$	ext{A ketone with the structure CH}_3	ext{COCH}_2	ext{CH}_3$$

Accepted Answer

2-Butanone

Question 15

Which mechanism best describes the reaction of aldehydes and ketones with alcohols to form acetals?

Accepted Answer

Nucleophilic addition followed by dehydration

Question 16

Which nitrogen nucleophile reacts with aldehydes to form imines?

Accepted Answer

Primary amines ($$	ext{RNH}_2)$$

Question 17

Which conditions are required for the hydrolysis of acetals back to aldehydes or ketones?

Accepted Answer

Aqueous acid

Question 18

A chemist wants to synthesize an aldehyde from a primary alcohol. Which reagent should they use?

Accepted Answer

PCC (Pyridinium chlorochromate)

Question 19

Which of the following best describes the outcome when a ketone reacts with a secondary amine?

Accepted Answer

An enamine is formed

Aromatic Compounds, Substitution Reactions, and Aldehydes & Ketones: Study Guide

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