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Basics of Organic Chemistry question

2022 · 28 Jul · Shift 2 · Q8
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Basics of Organic Chemistry question

2022 · 28 Jul · Shift 2 · Q8

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Arrange the following in increasing order of reactivity towards nitration A. p-xylene B. bromobenzene C. mesitylene D. nitrobenzene E. benzene Choose the correct answer from the options given below
  1. A
    C < D < E < A < B
  2. B
    D < B < E < A < C
  3. C
    D < C < E < A < B
  4. D
    C < D < E < B < A
View written solutionFree

Correct answer: B

  1. Identify the effect of each substituent on electrophilic aromatic substitution (nitration).
    Nitration is an electrophilic aromatic substitution reaction. The rate depends on whether the group already present on benzene is activating or deactivating.

  2. Analyze each compound.

    • D. Nitrobenzene: −NO2-NO_2−NO2​ is a very strong deactivating group due to both −I-I−I and −M-M−M effects. Hence it is the least reactive.

    • B. Bromobenzene: Halogens are overall deactivating in electrophilic substitution because of their strong −I-I−I effect, though they are ortho/para directing due to resonance donation. So bromobenzene is less reactive than benzene.

    • E. Benzene: reference compound.

    • A. p-Xylene: has two methyl groups. Each −CH3-CH_3−CH3​ group is activating by +I+I+I effect and hyperconjugation, so p-xylene is more reactive than benzene.

    • C. Mesitylene: has three methyl groups, so it is even more activated than p-xylene and thus the most reactive.

  3. Arrange in increasing order of reactivity.

Nitrobenzene<Bromobenzene<Benzene<p-xylene<Mesitylene\text{Nitrobenzene} < \text{Bromobenzene} < \text{Benzene} < p\text{-xylene} < \text{Mesitylene}Nitrobenzene<Bromobenzene<Benzene<p-xylene<Mesitylene

So,

D<B<E<A<CD < B < E < A < CD<B<E<A<C
  1. Match with the given options.

This corresponds to Option B.

  1. Compare with stored correct answer.
    Stored correct answer = B. This matches our derived answer.
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