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n-Propyl benzene can be obtained in quantitative yield by following method :
(i) By treating benzene with n-propyl chloride in presence of ${AlCl}_{3}$
(ii) By treating excess of benzene with n-propyl chloride in presence of ${AlCl}_{3}$
(iii) By treating benzene with allyl chloride in presence of ${AlCl}_{3}$ followed by reduction
(iv) By treating benzene with propionyl chloride in the presence of ${AlCl}_{3}$ followed by Clemmensen reduction.

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By (iii) and (iv)

By (ii), (iii) and (iv)

By (i), (iii) and (iv)

By (ii) only

answer is C.

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Detailed Solution

(i) and (ii) methods will form isopropyl benzene because n-propyl carbocation, being less stable, rearranges to the more stable $(2^{o})$ isopropyl carbocation. More ever, method

(i) will lead to polyalkylation. Methods (iii) and (iv) can be used for preparing n-propyl benzene.

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