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CHEM 242 - Aromatic Compounds and their Reactions - Ch15/16

Total questions: 87

Worksheet time: 2hrs 13mins

Name
Class
Date
1.

What is electrophilic substitution?

a)

A substitution reaction in which an electrophile is substituted for the electrons in the benzene ring

b)

A substitution reaction in which the benzene ring is attacked by a lone pair of electrons from an electrophile

c)

A substitution reaction in which an electrophile is attacked by the electrons in the benzene ring

2.

Which is least reactive in aromatic electrophilic substitution?

a)

Ethyl Benzene

b)

Anisole

c)

Acetophenone

d)

Chlorobenzene

3.

Which gives a meta nitro compound as the main product upon nitration with a nitric acid-sulfuric acid mixture?

a)

Ethyl Benzene

b)

Anisole

c)

Acetophenone

d)

Chlorobenzene

4.

With respect to the electrophilic aromatic substitution of benzene which of the following is not true?

a)

A non-aromatic intermediate is formed

b)

Benzene acts as an electrophile

c)

A proton is lost in the final step

d)

Resonance forms are important

5.

When considering electrophilic aromatic substitution reactions electron withdrawing substituents (e.g. cyano) are described as...

a)

Ortho/para directing and activating

b)

Ortho/para directing and deactivating

c)

Meta directing and activating

d)

Meta directing and deactivating

6.

What will be the attacking electrophile in the reaction of halogenation of Benzene?

a)

Halonium ion

b)

carbocation

c)

Benzene

d)

Halogen

7.

Why does benzene undergo substitution reactions rather than addition reactions

a)

Benzene is a planar, aromatic compound

b)

All the carbon atoms in benzene is sp2 hybridised

c)

All the carbon-carbon bonds in benzene is strong

d)

Benzene has extra stability due to the delocalized π electrons

8.

Aromatic compounds usually undergo which type of reaction

a)

Electrophilic substitution reaction

b)

Electrophilic addition reaction

c)

Nucleophilic substitution reaction

d)

Nucleophilic addition reaction

9.

Which of these is an activating group?

a)

NH2

b)

NO2

c)

COCH3

d)

SO3H

10.

Which is deactivating group?

a)

OH

b)

CHO

c)

CH3

d)

OCH3

11.

What is the reagent used in reaction 3?

a)

HNO3+H2SO4

b)

H2SO4

c)

Cl2/AlCl3

d)

CH3Cl/ AlCl3

12.

What is the reagent used in reaction 1?

a)

HNO3+H2SO4

b)

H2SO4

c)

Cl2/AlCl3

d)

CH3Cl/ AlCl3

13.

What is the reagent used in reaction 4?

a)

HNO3+H2SO4

b)

H2SO4

c)

Cl2/AlCl3

d)

CH3CH2Cl/ AlCl3

14.

Identify the product (s).

a)

I

b)

II

c)

I & II

d)

I & III

e)

II & III

15.
a)

I

b)

II

c)

I & III

d)

II & IV

16.

What is the product when methylbenzene(CH3)C6H5 react with HNO3/H2SO4?(More than 1 answer is allow)

a)

Ortho-nitro-methylbenzene

b)

Meta-nitro-methylbenzene

c)

Para-nitro-methylbenzene

d)

No reaction

17.

Which is an electrophile?

a)

OCH3-

b)

NO2+

c)

OH-

d)

H2O

18.

What is an electrophile?

a)

A species that takes part in a reaction by donating a lone pair of electrons

b)

A species that takes part in a reaction by accepting a lone pair of electrons

c)

A species with a positive charge that takes part in a reaction

19.

What is electrophilic substitution?

a)

A substitution reaction in which an electrophile is substituted for the electrons in the benzene ring

b)

A substitution reaction in which the benzene ring is attacked by a lone pair of electrons from an electrophile

c)

A substitution reaction in which an electrophile is attacked by the electrons in the benzene ring

20.

What are delocalised electrons?

a)

Electrons that are not attached to any of the atoms in a molecule

b)

Electrons that are shared between more than two atoms in a molecule

c)

Electrons that are not attached to any one particular atom but free to move over all the atoms in a molecule

21.

What is acylation?

a)

Substitution of one of the hydrogen atoms of a benzene ring by an acyl group from an acyl chloride

b)

Addition to the benzene ring of an alkyl group from a halogenoalkane

c)

Addition to the benzene ring of an acyl group from an acyl chloride

22.

What is a Friedel-Crafts reaction?

a)

An electrophilic substitution reaction

b)

A reaction to form a C-C bond to an aromatic ring

c)

A reaction involving a Lewis acid

23.

What is the electrophile in the acylation of benzene?

a)

AlCl3

b)

CO+

c)

Cl+

d)

R-CO+

24.

Which of the following statements is correct about benzene?

a)

All 6 carbon atoms lie in the same plan

b)

The C-C bond lengths are all the same

c)

It has delocalized electrons

d)

All of them

25.

How many double bonds in the benzene molecule?

a)

1

b)

2

c)

3

d)

4

26.

Who discovered benzene's stable structure?

a)

Faraday

b)

Lomonosov

c)

Kekule

d)

Priestley

27.

Due to its cyclic structure with a surrounding cloud of delocalised electrons, benzene is accurately described by which of the following chemical adjectives?

a)

Pungent

b)

Smelly

c)

Odorous

d)

Aromaticity

28.

Am I Aromatic?

a)

Aromatic

b)

Non-Aromatic

29.

Am I Aromatic?

a)

Aromatic

b)

Non-Aromatic

30.

Am I Aromatic?

a)

Aromatic

b)

Non-Aromatic

31.

Am I Aromatic?

a)

Aromatic

b)

Non-Aromatic

32.

Am I Aromatic?

a)

Aromatic

b)

Non-Aromatic

33.

Am I Aromatic?

a)

Aromatic

b)

Non-Aromatic

34.

Am I Aromatic?

a)

Aromatic

b)

Non-Aromatic

35.

Am I Aromatic?

a)

Aromatic

b)

Non-Aromatic

36.

Am I Aromatic?

a)

Aromatic

b)

Non-Aromatic

37.

Am I Aromatic?

a)

Aromatic

b)

Non-Aromatic

38.

The reaction in which benzene reacts with alkyl halide in the presence of a lewis acid as a catalyst to produce alkylbenzene is known as ___________

a)

Nitration

b)

Halogenation

c)

Friedel-Crafts Acylation

d)

Friedel-Crafts Alkylation

39.

Which of the following is rate determining step in electrophilic substitution reaction?

a)

Generation of electrophile

b)

Attack by an electrophilic reagent on benzene ring

c)

Formation of product

d)

All of the mentioned

40.

Chlorination of toluene gives

a)

o-chlorotoluene

b)

m-chlorotoluene

c)

p-chlorotoluene

d)

o & p -chlorotoluene

41.

Which of the following is rate determining step in electrophilic substitution reaction?

a)

Generation of electrophile

b)

Attack by an electrophilic reagent on benzene ring

c)

Formation of product

d)

All of the mentioned

42.

Which of the following act as catalysis in the nitration of benzene?

a)

Conc. HCl

b)

Dil. HCl

c)

Conc. H2SO4

d)

Dil. H2SO4

43.

Chlorination of toluene gives

a)

o-chlorotoluene

b)

m-chlorotoluene

c)

p-chlorotoluene

d)

o & p -chlorotoluene

44.

The electrophile used in sulphonation is

a)

SO2

b)

SO3

c)

H2SO4

d)

H2S2O6

45.

Electrophile used in chlorination is

a)

chloride ion

b)

chloride free radical

c)

chloronium ion

d)

chlorine atom

46.

Which is not a correct resonating structure of carbocation formed in electrophilic substitution of aniline?

a)
b)
c)
d)
47.

Which of the following is not the correct resonating structure?

a)
b)
c)
d)
48.

Aromatic group reacts easily with

a)

OH-

b)

Cl-

c)

Br+

d)

H2O

49.

Which aromatic substitution requires catalyst Lewis acid

a)

Nitration

b)

Sulphonation

c)

Halogenation

d)

Alkylation

50.

Which is the correct drawing of o-bromonitrobenzene?

a)
b)
c)
d)
51.

These statements about aromatic compounds are correct EXCEPT

a)

They are cyclic and planar

b)

They follow Huckel's 4n rule

c)

They have conjugated double bonds

d)

They have delocalized undefinedelectrons

52.
How many delocalised electron are there for each benzene molecules?
a)
2
b)
3
c)
6
d)
12
53.

Which of the following molecules is aromatic?

a)
b)
c)
d)
54.

Name the following compound

a)

Benzene

b)

Benzol

c)

Phenyl

d)

Phenol

55.

Use your understanding of the bonding in benzene to identify the compound that has the most exothermic enthalpy of hydrogenation.

a)
b)
c)
d)
56.

Why does aromatic compounds prefer to undergo electrophilic substitution reaction?

a)

Aromatic compounds are electron rich so they attract electrophiles

b)

Aromatic compounds are electron rich so they attract nucleophiles

c)

Aromatic compounds are electron poor so they attract electrophiles

d)

Aromatic compounds are electron poor so they attract nucleophiles

57.

Name the compound (hint: you can chose more than one answer)

a)

Nitro benzene

b)

Ammonia benzene

c)

Aniline

d)

amino benzene

58.

Name the compound

a)

Methane benzene

b)

Toluene

c)

Benzene methane

d)

methane phenyl

59.

For benzene; Which of the statements is/are correct?

a)

It is an aromatic compound.

b)

Its empirical formula is CH.

c)

It contains 3 π and 12 σ bonds.

60.
What is the C-C Bond angle in benzene?
a)
1200
b)
1200 & 109.50
c)
109.50
d)
104.50 & 1200
61.

What is reagent X?

a)

CH3CH2Br, AlBr3

b)

CH3Br, AlBr3

c)

CH3CH2CH2Br, AlBr3

d)

CH3CH(Br)CH3, AlBr3

62.

What is the product F?

a)
b)
c)
d)
63.

Which of the following molecule is aromatic?

a)

I

b)

II

c)

III

d)

IV

64.

In an electrophilic substituted reaction, Halobenzenes are

a)

Ortho director

b)

Para director

c)

Ortho and para director

d)

Meta director

65.

Choose the incorrect statement(s)

a)

All activating groups are ortho and para director

b)

Weakly deactivating groups like halogens are ortho and para director

c)

Strongly deactivating groups are ortho and para director

d)

Activating groups increases the rate of electrophilic substitution reaction

66.

Which is most reactive in aromatic electrophilic substitution?

a)

Ethyl Benzene

b)

Anisole

c)

Acetophenone

d)

Chlorobenzene

67.

What does the o in o-Xylene means?

a)

ortho

b)

one

c)

opposite

d)

Original

68.

What is the reaction called for the production of styrene produced from ethylbenzene?

a)

Dehydrogenation

b)

Dehydration

c)

Alkylation

d)

Alkenation

69.

Aromatic compounds are non-polar and so they are not soluble in polar water solvent. Is the statement true or false?

a)

True

b)

False

70.

Which one of the following is the chemical formula for ethyl benzene?

a)

C6H5CHCH2

b)

C6H5CH2CH3

c)

C8H10

71.

What is this compound?

a)

P-xylene

b)

m-xylene

c)

o-xylene

d)

Toluene

72.

TRUE OR FALSE:

FeBr3 is a good catalyst in the bromination of benzene.

a)

TRUE

b)

FALSE

73.

TRUE OR FALSE:

Sulfonation is a reversible process.

a)

TRUE

b)

FALSE

74.

a)

Aromatic

b)

Anti-Aromatic

c)

Non-Aromatic

75.
a)

Aromatic

b)

Anti-Aromatic

c)

Non-Aromatic

76.

Why can you get polyalkylation after the first Friedel-Crafts Alkylation?

(a)  

77.

Which is NOT one of the four limitations of Friedel-Crafts Alkylation?

a)

Vinyl and aryl halides can be used

b)

Aromatics must not contain a strong deactivating group or an amine

c)

carbocation rearrangement may occur in any reaction containing a carbocation

d)

polyalkylation

78.

What would be the product of aniline undergoing a Friedel-Crafts Alkylation

a)

b)

c)

d)

79.

Which nitration product will form faster - nitration of aniline or nitration of nitrobenzene

(a)  

80.

Does Bromide activate or deactivate the ring?

a)

Neither

b)

Both

c)

Activate

d)

Deactivate

81.

True or False: Benzylic Radical is more stable than an alkyl radical

a)

True

b)

False

82.

What is wrong with the following reaction:

a)

NO2 should be ortho or para

b)

H2 Pd/C cannot reduce an aldehyde

c)

Bromine should be meta

d)

Nothing is wrong

83.

Name this compound

a)

amidobenzene

b)

acetanilide

c)

benzoic acid

d)

aminobenzene

84.
a)

Benzoic acid

b)

Amidobenzene

c)

aminobenzene

d)

phenol

85.

Name this compound

a)

Benzoic Acid

b)

Aniline

c)

Anisole

d)

phenol

86.

Name this compound

a)

3-carboxylic-1-bromobenzene

b)

3-bromobenzoic acid

c)

2-bromophenyl-carboxylic acid

d)

3-bromo-Anisole

87.

What is the common name?

a)

xylene

b)

toluene

c)

ethylbenzene

d)

methylbenzene

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