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Aromaticity

Total questions: 60

Worksheet time: 52mins

Name
Class
Date
1.

Which of the following is aromatic?

a)

A

b)

B

c)

C

d)

D

e)

E

2.

Which of the following has significant resonance stabilization?

a)

I

b)

II

c)

III

d)

None

e)

All of the above

3.

Which is NOT aromatic?

a)

I

b)

II

c)

III

d)

IV

e)

V

4.

Which reagent can be used as a simple chemical test to distinguish between benzene and 1-hexene?

a)

A

b)

B

c)

C

d)

D

e)

E

5.

How many equivalent resonance structures can be drawn for the cyclopentadienyl anion?

a)

3

b)

6

c)

5

d)

2

6.

Consider the molecular orbital diagram of benzene. In ground state, how many molecular orbitals are filled with electrons?

a)

6

b)

3

c)

1

d)

2

7.

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

a)

All of the atoms are sp2 hybridized

b)

Cyclopentadiene is aromatic

c)

Removal of a hydride ion yields a highly stable aromatic cation

d)

Removal of a proton yields a highly stable aromatic anion

8.
a)

I

b)

II

c)

III

d)

IV

9.

Choose the correct statement

a)

Carbon to carbon bond in benzene have the same bond length

b)

Cyclobutene has delocalised electrons

c)

C=C bond in cyclobutene is longer than C-C bond in butane

d)

All atoms in cyclobutene, pentane and benzene are planar

10.

Which compound below is aromatic?

a)
b)
c)
11.

Which of the following statements about benzene is true?

a)

All the six hydrogens are on a different plane.

b)

The actual benzene structure is the rapid equilibrium of the two Kekule's structure.

c)

All carbon atoms are sp-hybridised.

d)

Benzene is a gas at room temperature.

12.

Which of the following compound is aromatic haloalkane?

I. C6H5Cl

II. C6H5CH2Cl

III. CH3CH2Cl

a)

I only

b)

I and II only

c)

II and III only

d)

I, II and III

13.

Choose the correct statement

a)

Carbon to carbon bond in benzene have the same bond length

b)

Cyclobutene has delocalised electrons

c)

C=C bond in cyclobutene is longer than C-C bond in butane

d)

All atoms in cyclobutene, pentane and benzene are planar

14.

Aromatic compounds usually undergo which type of reaction?

a)

Electrophilic substitution reaction

b)

Electrophilic addition reaction

c)

Nucleophilic substitution reaction

d)

Nucleophilic addition reaction

15.

Does benzene decolorise bromine?

a)

Yes

b)

NO

16.

How many delocalised electrons (pi electrons) are there for each benzene molecule?

a)

2

b)

3

c)

6

d)

12

17.

Which compound below is aromatic?

a)
b)
c)
d)
18.

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

a)
b)
c)
d)
19.

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

20.

What is the minimum number of carbon for the simplest aromatic compound?

a)

4

b)

6

c)

8

d)

12

21.

Aromatic compounds are polar and insoluble in water. Is the statement true or false?

a)

True

b)

False

22.

The ratio of carbon to hydrogen for aromatic compounds are ________________, which is why they usually don't burn completely.

a)

High

b)

Low

23.

Aromatic compounds usually undergo which type of reaction?

a)

Electrophilic substitution reaction

b)

Electrophilic addition reaction

c)

Nucleophilic substitution reaction

d)

Nucleophilic addition reaction

24.

The following are the methods to extract aromatic compounds from non-aromatic compounds except ________________.

a)

Liquid-liquid extraction

b)

Distillation, Extractive or Azeotropic distillation

c)

Adsorption

d)

Crystallisation

e)

Absorption

25.

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

26.

Which of the following molecule is aromatic?

a)

I

b)

II

c)

III

d)

IV

27.

Choose the correct statement(s) for aromatic compounds 

a)

They are cyclic and planer

b)

The follow Huckel's 4n rule

c)

They have conjugated double bonds

d)

They have  \pi delocalized electrons

28.

The name of the intermediate of an electrophilic aromatic substitution is

(a)  

29.

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.

30.

Which of the following molecules is aromatic?

a)
b)
c)
d)
31.

Benzene can only undergoes reaction of ______________

a)

elimination

b)

addition

c)

substitution

d)

none

32.

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

a)
b)
c)
d)
33.

Which one of the following does not contain any delocalised electrons?

a)

poly(propene)

b)

benzene

c)

graphite

d)

sodium

34.

Which of the following is FALSE about ethene and benzene?

a)

A. Both are planar molecules

b)

B. Both are non-polar molecules

c)

C. Both exhibit sp2 hybridisation

d)

D. Both have the same C:H ratio

35.

Which of the following reagent does not react with benzene?

a)

A. Concentrated H2SO4

b)

B. HNO3/ H2SO4

c)

C. Iodoehane in the presence of iron

d)

D. Sodium hydroxide solution

36.

The species that attacks the benzene molecule in the nitration of benzene using a mixture of concentrated sulphuric acid and concentrated nitric acid is

a)

A. ⋅NO2

b)

B. NO2+

c)

C. HNO3

d)

D. NO3 -

37.

Which of the following structures does not exist?

a)
b)
c)
d)
38.

Benzene can only undergoes reaction of ______________

a)

elimination

b)

addition

c)

substitution

d)

none

39.

What is the C-C Bond angle in benzene?

a)

1200

b)

1200 & 109.50

c)

109.50

d)

104.50 & 1200

40.

How many degrees of unsaturation is present in benzene?

a)

5

b)

4

c)

6

d)

3

41.

This mono-substituted benzene with a common name has a vinyl group attached to the phenyl ring

a)

What is allyl benzene?

b)

What is Styrene?

c)

What is Vinylbenzyl?

d)

What is Benzenethene?

42.

Which of the following is considered an aromatic ether?

a)

Aniline

b)

Phenol

c)

Acetophenone

d)

Anisole

43.

Benzene is ......

a)

trigonal planar

b)

tetrahedral

c)

planar

d)

hexagonal

44.

What did Kekulé suggest as a structure for benzene?

a)

A long, long chain of carbons and hydrogens with alternating single and double bonds between the carbons

b)

A 3D cage of carbons with a complex system of bonds between them, with one hydrogen attached to each carbon

c)

A ring of six carbons with alternating single and double bonds between the carbons, with one hydrogen atom bonded to each carbon

d)

A ring of six carbon atoms with a stable, delocalised system of s-electrons forming bonds between the carbons and the single hydrogen atom bonded to each carbon

45.
What is the accepted current view of the model for bonding in benzene?
a)
Delocalised model
b)
Kekule structure
c)
Resonance structure
d)
Arrhenius structure
46.

Which of the following represents the lowest energy bonding π molecular orbital of benzene?

a)

4

b)

3

c)

2

d)

1

47.

Which of the following compounds is aromatic?

a)

ethane

b)

cyclooctatetraene

c)

cyclobutadiene

d)

benzene

48.

Which of the following compounds is antiaromatic?

a)

ethane

b)

cyclobutadiene

c)

cyclooctatetraene

d)

benzene

49.

Which of the following is formed by Diels-Alder dimerization of cyclobutadiene?

a)

3

b)

4

c)

1

d)

2

50.

Which of the following ions is aromatic?

a)

1

b)

2

c)

3

d)

4

51.

Which of the following molecules is the strongest acid?

a)

1

b)

2

c)

3

d)

4

52.

Which of the following heterocycles is not aromatic?

a)

1

b)

2

c)

3

d)

4

53.

Which of the following represents the energy levels of the six π molecular orbitals of benzene?

a)

1

b)

2

c)

3

d)

4

54.

Which of the following features accounts for the downfield shift of the signal in the 1H NMR spectrum for the hydrogen atoms of benzene?

a)

The N+1 rule

b)

The presence of electronegative elements

c)

The presence of six identical protons

d)

Ring currents which reinforce the applied field

55.

Why is there a huge gain in the stability of benzene's double bonds compared to cyclohexene?

a)

Cyclic congugation increases the number of p orbital interactions in the conjugated system, stabilizing the pi bonds. Cyclohexene lacks this stability, and the energy of its pi bond is greater (less stable).

b)

The linear conjugation of the cyclohexene makes it less stable

c)

Cyclic congugation increases the number of p orbital interactions in the conjugated system, stabilizing the pi bonds. Cyclohexene has only linear delocalized pi electrons.

56.

Choose the answer that best fills in the blanks of the following statement:

An aromatic must have _____________ of pi electrons, above and below the _____ of the molecule. This cloud must have an ________ of electon pairs.

a)

A uniform cloud, plane, even number

b)

An uninterrupted cyclic cloud, plane, odd number

c)

A high energy cloud, most polar region, odd number

d)

A low energy clod , plane , even number

57.

[10]-annulene is not an aromatic compound becuase it is not (a)   . This causes it to be classified as a non aromatic.

58.

Why would a compound be anti-aromatic?

a)

If a compound has a 4n number of pi electrons, it will be anti-aromatic.

b)

If a compound fits Huckel's Rule

c)

If a compound cannot escape being planar and has 4n number of pi electrons.

d)

If a compound has an odd number of atoms in its ring structure.

59.

Which of the following are aromatic?

Cyclopropene, Cyclopropenyl cation, Cycloheptatrienly cation, Cycloheptatrenyl anion?

a)

Cyclopropenyl cation, Cycloheptatrienly cation

b)

Cyclopropene, Cycloheptatrienly cation, Cycloheptatrenyl anion

c)

Cyclopropenyl cation

d)

Cyclopropene, Cyclopropenyl cation, Cycloheptatrienly cation, Cycloheptatrenyl anion

60.

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