Deck 13: Benzene and Its Derivatives

Question 1

On what basis was the name aromatic originally given to compounds?

A) They had strong odors.
B) Their first application was in aromatherapy.
C) Their odors were considered to be pleasant.
D) Their odors were considered to be unpleasant.

Answer 1

C

Question 2

Which of the following compounds is an aldehyde?

A)
B)
C)
D)

Answer 2

B

Question 3

Which of the following observations was troublesome to 19^th century chemists?

A) Benzene contains more hydrogen atoms than expected.
B) Benzene does not undergo combustion.
C) Benzene does not react similarly to alkenes.
D) Benzene reacts similarly to alkenes.

Answer 3

C

Question 4

Which of the following is true of the reactivity of benzene?

A) It reacts readily with bromine to form 1,2-dibromobenzene.
B) It can be readily hydrogenated with H₂/Pd.
C) It reacts readily with HBr to form bromobenzene.
D) None of the above is true.

Question 5

What is an acceptable name of the following compound?

A) o-dimethylbenzene
B) m-dimethyllbenzene
C) p-diethylbenzene
D) m-diethylbenzene

Question 6

Which of the following correctly describes the two aromatic ring substituents in the xylenes?

A) They are both hydroxyl groups.
B) They are both methyl groups.
C) One is a methyl and one is an hydroxyl.
D) One is a methyl and one is an ethyl.

Question 7

Which of the following was true of Kekulé's proposal for the structure of benzene?

A) It was readily accepted.
B) It was rejected because it was inconsistent with experiment.
C) It was not readily accepted since it did not account for the very different reactivity of benzene compared with alkenes.
D) It was not readily accepted since it did not account for the known structure of benzene.

Question 8

What is the most specific name for the C₆H₅− group?

A) aryl
B) arenyl
C) phenol
D) phenyl

Question 9

Which of the following compounds is a carboxylic acid?

A)
B)
C)
D)

Question 10

Which of the following compounds is an aliphatic hydrocarbon?

A) aniline
B) anisole
C) phenol
D) none of these

Question 11

Which of the following statements about the structure of benzene is true?

A) All the C-C bonds in benzene are longer than a typical C=C.
B) All the C-H bonds in benzene are longer than a typical C-H bond.
C) The benzene molecule contains alternating double and single bonds.
D) Benzene is a 1:1 mixture of two equilibrating structures.

Question 12

Which of the following compounds is anisole?

A)
B)
C)
D)

Question 13

Which of the following chemists contributed to our understanding of the structure and bonding in benzene?

A) Linus Pauling
B) Friedrich August Kekulé
C) Both a and b
D) Neither a nor b

Question 14

Which of the following compounds is an amine?

A) aniline
B) anisole
C) phenol
D) toluene

Question 15

Which of the following is an appropriate definition of an aromatic compound?

A) Any compound that contains one or more benzene-like rings
B) Any compound that contains one or more 6-membered rings.
C) Any compound that contains a double bond within a 6-membered ring.
D) Any compound with a pleasant odor.

Question 16

Which of the following compounds is an ether?

A) aniline
B) anisole
C) phenol
D) toluene

Question 17

Which of the following is one of the starting materials in the manufacture of Dacron?

A) o-xylene
B) m-xylene
C) p-xylene
D) none of these

Question 18

Which of the following is true of the C-C bonds in benzene?

A) They are shorter than typical C-C single bonds
B) They have the same length as typical C-C single bonds
C) They are longer than typical C-C single bonds but shorter than typical C=C double bonds
D) They have the same length as typical C-C double bonds

Question 19

Which of the following best describes the odors of aromatic compounds?

A) They all have strong odors.
B) They all have pleasant odors.
C) They all have unpleasant odors.
D) Some have pleasant odors, some have unpleasant odors, and some are odorless.

Question 20

What is the correct IUPAC name of the following compound?

A) 1-ethyl-4-bromobenzene
B) 4-ethyl-1-bromobenzene
C) 1-bromo-4-ethylbenzene
D) 4-bromo-1-ethylbenzene

Question 21

The conversion of nitrobenzene to aniline is an example of which of the following?

A) reduction
B) oxidation
C) substitution
D) none of these

Question 22

How many constitutional isomers are possible when there are three identical substituents on a benzene ring?

A) 2
B) 3
C) 4
D) 5

Question 23

Which of the following structures represents m-nitrobenzoic acid?

A)
B)
C)
D)

Question 24

If both a methyl group and a hydroxyl group are attached to a benzene ring, which of the following is the preferred way to name the compound in the IUPAC system?

A) as a hydroxymethylbenzene
B) as a hydroxytoluene
C) as a methylphenol
D) all of these are equally acceptable

Question 25

Which of the following explosives does not include a ring as part of its structure?

A) nitroglycerine
B) RDX
C) TNT
D) none, they all include a ring

Question 26

What reagents are used to convert nitrobenzene to aniline?

A) H₂ in the presence of a Ni catalyst
B) sulfuric acid
C) nitric acid in the presence of sulfuric acid
D) Ni in the presence of sulfuric acid

Question 27

Which aromatic ring substitution reaction is used in the preparation of synthetic detergents?

A) reduction
B) halogenation
C) nitration
D) sulfonation

Question 28

Match up the applications to the compounds shown below?

A) (i) explosive; (ii) detergent
B) (i) detergent; (ii) explosive
C) (i) explosive; (ii) vitamin
D) (i) vitamin; (ii) detergent

Question 29

Which of the following structures represents 2,4,6-tribromophenol?

A)
B)
C)
D)

Question 30

In a phenol, which group is the substituent on the benzene ring?

A) amino
B) carbonyl
C) carboxyl
D) hydroxyl

Question 31

The structure of benzo[a]pyrene has how many 6-membered rings?

A) 3
B) 4
C) 5
D) 6

Question 32

What is produced when benzene reacts with chlorine in the presence of an iron catalyst?

A) only chlorobenzene
B) chlorobenzene and chlorine atoms
C) chlorobenzene and hydrogen chloride
D) chlorobenzene and water

Question 33

What organic product is formed when benzene reacts with nitric acid in the presence of concentrated sulfuric acid?

A)
B)
C)
D)

Question 34

Which of the following is a correct IUPAC name?

A) 1,2-dichloro-4-bromobenzene
B) 1-bromo-3,4-dichlorobenzene
C) 4-bromo-1,2-dichlorobenzene
D) 3,4-dichloro-1-bromobenzene

Question 35

Which of the following statements is false?

A) Anthracene is a polycyclic aromatic hydrocarbon.
B) Benzo[a]pyrene is a carcinogenic polynuclear aromatic hydrocarbon.
C) The most common polycyclic aromatic hydrocarbons are found in natural gas.
D) Naphthalene was once used as mothballs.

Question 36

Which of the following is a polynuclear aromatic hydrocarbon with three rings in a linearly fused arrangement?

A) anthracene
B) benzene
C) naphthalene
D) phenanthrene

Question 37

What is produced when benzene reacts with nitric acid in the presence of sulfuric acid?

A) only nitrobenzene
B) nitrobenzene and NO
C) nitrobenzene and NO₂
D) nitrobenzene and water

Question 38

What is the IUPAC name for the following compound?

A) 1-amino-2-chloro-5-bromobenzene
B) 5-bromo-2-chloroaniline
C) 1-chloro-4-bromo-2-aniline
D) 4-bromo-1-chloro-2-aniline

Question 39

Which of the following statements is false?

A) Anisole is an aromatic ether.
B) Phenanthrene contains an OH group bonded to an aromatic ring.
C) Aniline is an aromatic amine.
D) The C₆H₅- substituent is called a phenyl group.

Question 40

Which of the following is a correct IUPAC name?

A) 2-chloro-3-bromotoluene
B) 3-bromo-2-chlorotoluene
C) 2-chloro-4-bromotoluene
D) 6-bromo-4-chlorotoluene

Question 41

In the radical chain propagation steps during the autoxidation of unsaturated fatty acids, which of the following statements is false?

A) Oxygen reacts with an alkyl radical to form a hydroperoxy radical.
B) A hydroperoxy radical abstracts a hydrogen atom from another fatty acid molecule.
C) Two hydroperoxy radicals combine to give a peroxy product.
D) None, all these statements are true.

Question 42

Which of the following is the correct IUPAC name of the following compound?

A) 1-propylphenol
B) 2-propylphenol
C) 2-hydroxypropylbenzene
D) 2-propyl-1-hydroxybenzene

Question 43

Which reagents/catalysts would be needed to convert benzene to p-bromonitrobenzene?

A) Br₂/FeBr₃
B) HNO₃/H₂SO₄/Heat
C) NaOH
D) H₂SO₄/Heat
E) both a and b

Question 44

Consider the following structure. If a chlorine at were substituted for each of the labeled hydrogen atoms, which of the following is true of the resulting compound?

A) Could exist as cis-trans isomers.
B) Would represent the meta isomer.
C) Would represent the 1,4 isomer.
D) Both b and c would be correct.

Question 45

Which of the following is the correct IUPAC name of the following compound?

A) 1-ethyl-4-hydroxybenzene
B) 4-ethylphenol
C) 1-hydroxy-4-methylbenzene
D) phenolstyrene

Question 46

p-bromonitrobenzene is treated with hydrogen gas in the presence of a Pd catalyst. What would be the product of the reaction?

A) 4-bromoaniline
B) benzene
C) bromobenzene
D) nitrobenzene

Question 47

Of the molecules catechol, hydroquinone, resorcinol and thymol, which is not an isomer of the other three?

A) catechol
B) hydroquinone
C) resorcinol
D) thymol

Question 48

Which of the following compounds is produced by the body as a natural "radical scavenger"?

A)
B)
C)
D) All three compounds are naturally occurring radical scavengers.

Question 49

Consider the following compound, albuterol, used in bronchodialators. How many acidic groups are present in this compound?

A) 1
B) 2
C) 3
D) 4

Question 50

How many unpaired electrons are present in an oxygen molecule?

A) 0
B) 1
C) 2
D) 4

Question 51

Which of the following is the correct IUPAC name of the following compound?

A) 2-hydroxy-4-methyl-1-nitrobenzene
B) 4-methyl-1-nitro-2-phenol
C) 5-methyl-2-nitrophenol
D) 1-nitro-2-hydroxy-4-methylbenzene

Question 52

Which of the following compounds is found in peppers?

A) capsaicin
B) hydroxyquinone
C) thymol
D) urushiol

Question 53

Consider the following compound, BHT, used as an antioxidant in foods. Which of the following describes the product of the reaction of this compound with NaOH?

A) phenoxide
B) hydroperoxide
C) hydrocarbon
D) None of these, BHT will not react with NaOH.

Question 54

The reaction of oxygen with an unsaturated fatty acid gives which of the following products?

A) a phenol
B) a hydroperoxide
C) vitamin E
D) none of the above

Question 55

Which of the following is a common feature of catechol, hydroquinone, and resorcinol?

A) They all have two methyl groups as substituents on a benzene ring.
B) They all have two hydroxyl groups as substituents on a benzene ring.
C) They all have one methyl and one hydroxyl as substituents on a benzene ring.
D) None of the above, these compounds do not have any common features.

Question 56

Consider the following structure. Which of the following correctly applies to this structure?

A) It is called an arene.
B) It is classified as an aromatic compound.
C) All carbon to carbon bonds are equivalent.
D) All hydrogen atoms are equivalent.
E) All of the above apply to this structure.

Question 57

Consider the following step is the autoxidation of a fatty acid. Which step of the mechanism does this represent?

A) chain initiation
B) chain propagation
C) chain termination
D) None of these, this is an oxidation.

Question 58

Consider the following structure. This is commonly called BHT which is an antioxidant added to food. In the IUPAC name for this compound, the -OH group would correspond to which position in the numbering scheme?

A) 1
B) 2
C) 4
D) 5
E) 6

Question 59

Consider the following structure. If one of the hydrogen atoms were replaced with an -NH₂ group and another with a -Br group, the compound would as named as which of the following?

A) a derivative of benzene
B) a derivative of bromobenzene
C) a derivative of aminobenzene
D) a derivative of aniline
E) a derivative of anisole

Question 60

Which of the following compounds is found in the oil of poison ivy?

A) capsaicin
B) hydroxyquinone
C) thymol
D) urushiol