Question 1

Which of the following reagents is most appropriate for the nitration of benzene to form nitrobenzene?

Accepted Answer

$$\mathrm{$$HNO_3$$}$$ and $$\mathrm{H_2SO_4}$$

Question 2

A chemist wants to introduce a sulfonic acid group ($$\mathrm{SO_3H}) $$onto a benzene ring. Which set of reagents should be used?

Accepted Answer

$$\mathrm{SO_3$}$$ and $$\mathrm{H_2SO_4}$$

Question 3

Which of the following substituents on a benzene ring will direct incoming electrophiles to the ortho and para positions during electrophilic aromatic substitution?

Accepted Answer

$$\mathrm{OH}$$

Question 4

A student treats toluene with $$\mathrm{$$KMnO_4$$}$$ under acidic conditions. What is the major product?

Accepted Answer

Benzoic acid ($$\mathrm{C_6H_5COOH})$$

Question 5

Which of the following sequences will convert a nitrobenzene to an aniline ($$\mathrm{C_6H_5NH_2}$$)?

Accepted Answer

$$\mathrm{NO_2$}$$ $$\xrightarrow{\mathrm{H_2},\ \mathrm{Pd/C}}$$ $$\mathrm{NH_2$}$$

Question 6

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

Accepted Answer

Toluene $$\u003e$$ Benzene $$\u003e$$ Nitrobenzene

Question 7

A chemist wants to brominate anisole ($$\mathrm{C_6H_5OCH_3}). $$Which positions on the ring will be most favored for substitution?

Accepted Answer

Ortho and para positions

Question 8

Which of the following is the best method to reduce a nitro group ($$\mathrm{NO_2$}) to an $$amine ($$\mathrm{NH_2$}) on a $$benzene ring?

Accepted Answer

$$\mathrm{Sn}$$ and $$\mathrm{HCl}$$

Question 9

Which of the following substituents is a meta-director in electrophilic aromatic substitution?

Accepted Answer

$$\mathrm{NO_2$}$$

Question 10

A benzene ring is substituted with a bromine atom. Which reagent will best introduce a nitro group at the meta position relative to the bromine?

Accepted Answer

None of the above; bromine is an ortho/para director, so meta substitution is not favored

Question 11

Which of the following transformations is achieved by the use of $$\mathrm{Zn(Hg)}$$ and $$\mathrm{HCl} ($$Clemmensen reduction)?

Accepted Answer

Reduction of a carbonyl group to a methylene group

Question 12

A student wants to synthesize $$p-$$bromonitrobenzene from benzene. Which sequence of reactions is most efficient?

Accepted Answer

Bromination, then nitration

Question 13

Which of the following statements best explains why $$\mathrm{NO_2$} is a $$meta-directing group?

Accepted Answer

It destabilizes the ortho and para intermediates due to electron withdrawal

Question 14

Which of the following is the correct product when benzene is treated with $$\mathrm{Cl_2$}$$ and $$\mathrm{$$FeCl_3$$}$$?

Accepted Answer

Chlorobenzene

Question 15

A chemist oxidizes ethylbenzene with $$\mathrm{$$KMnO_4$$}. $$What is the major product?

Accepted Answer

Benzoic acid

Question 16

Which of the following reagents will convert a methyl group on a benzene ring to a carboxylic acid group?

Accepted Answer

$$\mathrm{$$KMnO_4$$}$$

Question 17

Which of the following is the best explanation for why $$\mathrm{OH} is an $$activating group in electrophilic aromatic substitution?

Accepted Answer

It donates electrons to the ring via resonance and induction

Question 18

A chemist wants to introduce a nitro group at the meta position of benzoic acid. Which of the following is the correct sequence?

Accepted Answer

Nitration of benzoic acid

Question 19

Which of the following is the correct product when phenol is treated with $$\mathrm{Br_2$} in $$water?

Accepted Answer

2,4,6-tribromophenol

Question 20

Which of the following best describes the effect of an $$\mathrm{NH_2$}$$ group on the reactivity of a benzene ring toward electrophilic aromatic substitution?

Accepted Answer

It activates the ring and is an ortho/para director

Aromatic Substitution and Functional Group Transformations – Organic Chemistry Study Guide

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