Sample 1Easy
Despite its unsaturation, benzene mainly undergoes
- A
nucleophilic substitution reactions
- B
electrophilic substitution reactions
- C
free radical addition reactions
- D
nucleophilic addition reactions
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The answer is B.The delocalised π electrons make benzene unusually stable and a source of electrons. It therefore mainly undergoes electrophilic substitution, as in nitration, halogenation and Friedel-Crafts reactions.
- A.
The electron-rich ring repels nucleophiles.
- C.
Addition, possible only under special conditions, would destroy the stable delocalised system.
- D.
Benzene has no polar multiple bond for a nucleophile to attack.
NCERT: Class 11 Chemistry, Unit 9 (Hydrocarbons), Aromatic Hydrocarbons: Chemical Properties
Sample 2Medium
Which of the following species is aromatic?
- A
Cyclopentadienyl cation
- B
Cyclopentadienyl anion
- C
Cyclooctatetraene (non-planar tub form)
- D
Cyclopenta-1,3-diene
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The answer is B.An aromatic species must be cyclic, planar, fully conjugated and contain (4n + 2) π electrons. The cyclopentadienyl anion is planar with all five carbons sp2 and has 6 π electrons (n = 1).
- A.
The cation has only 4 π electrons, which does not satisfy the (4n + 2) rule.
- C.
The tub-shaped molecule is non-planar and has 8 π electrons, so it is not aromatic.
- D.
Cyclopentadiene has an sp3 CH2 carbon, so its π system is not completely delocalised around the ring.
NCERT: Class 11 Chemistry, Chapter 9, 9.5