Q: What is the molecular formula for benzenesulfonic acid?

$$\text{C}_6\text{H}_5\text{SO}_3\text{H}$$

Question 1

What is the most appropriate name for the following compound: $$\displaystyle 	ext{C}_6	ext{H}_5	ext{CH}_2	ext{CH}_3$$?

Accepted Answer

1-phenylethane

Question 2

Cyclooctatetraene should be antiaromatic and quite unstable according to Hückel, yet this compound is commercially available and reasonably stable. What is the most plausible reason for this?

Accepted Answer

This compound probably adopts a non-planar shape, thereby staying non-aromatic

Question 3

Consider the preparation of deuterated benzene by treatment of benzene with deuterated sulfuric acid. What type of mechanism is plausible in this case?
$$\displaystyle 	ext{C}_6	ext{H}_6 + 	ext{D}_2	ext{SO}_4 ightarrow 	ext{C}_6	ext{D}_6 + 	ext{H}_2	ext{SO}_4$$

Accepted Answer

Electrophilic substitution with D$$^+ as $$the electrophile

Question 4

Which of the following is NOT an ortho-para director in electrophilic aromatic substitution?

Accepted Answer

$$-	ext{COOH}$$

Question 5

What is the molecular formula for benzenesulfonic acid?

Accepted Answer

$$	ext{C}_6	ext{H}_5	ext{SO}_3	ext{H}$$

Question 6

Which of the following compounds is aromatic?

Accepted Answer

III only

Question 7

Consider the molecular orbital model of 1,3-cyclobutadiene and sketch Frost's circle: how many electrons are in non-bonding molecular orbitals?

Accepted Answer

4

Question 8

Only one of the following compounds is a hemiacetal. Which one?

Accepted Answer

C

Question 9

On tribromobenzene isomer 1,2,3-tribromobenzene, overall, how many isomeric tribromobenzenes exist?

Accepted Answer

Four

Question 10

The major product(s) of the following reaction would be:
$$\displaystyle 	ext{C}_6	ext{H}_5	ext{Cl} + 	ext{SO}_3	ext{H}_2	ext{SO}_4 ightarrow$$

Accepted Answer

III only

Question 11

Which of the following groups is a formyl group?

Accepted Answer

A formyl group

Question 12

Which of the following compounds would be most reactive to ring bromination?

Accepted Answer

V

Question 13

Toluene is the name commonly assigned to:

Accepted Answer

Methylbenzene

Question 14

The electrophile in the sulfonation of benzene is:

Accepted Answer

$$	ext{SO}_3$$

Question 15

Several conditions have to hold for a compound to be aromatic. Only one of the conditions below is NOT essential for aromaticity. Which one?

Accepted Answer

Aromatic compounds must show a ring current in the NMR

Question 16

What class of compounds does the product of the following reaction belong to?
$$\displaystyle 	ext{Ph}-	ext{NH}_2 + 	ext{CHO} \xrightarrow{	ext{H}_2	ext{O}}$$

Accepted Answer

Imine

Question 17

Which of these is an aromatic molecule?

Accepted Answer

III

Question 18

Cyclopentadiene is unusually acidic for a hydrocarbon. An explanation for this is the following statement:

Accepted Answer

The conjugate base of cyclopentadiene is an aromatic anion

Question 19

Which one is the least reactive towards electrophiles?

Accepted Answer

Nitrobenzene

Question 20

Benzoic acid, $$	ext{C}_6	ext{H}_5	ext{COOH}$$, will:

Accepted Answer

Nitrate slowly in the meta position

Question 21

How many peaks would you expect to see in the proton NMR spectrum of the aromatic cyclopentadienyl cation?

Accepted Answer

One only

Aromatic Compounds and Electrophilic Aromatic Substitution: Study Guide

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