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Q.

n-Propylbenzene can be obtained in quantitative yield by following method :
(i) Bytreating benzene with n-propyl chloride in presence of AICI₃
(ii) By treating excess of benzene with n-propyl chloride in presence of AICI₃
(iii) By treating benzene with allyl chloride in presence of AICI₃ followed by reduction
(iv) Bytreating benzene with propinoyl chloride in presence of AICI₃ followed by Clemmensen reduction.

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a

By (iii) and (iv)

b

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

c

By(ii) only

d

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

answer is C.

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Detailed Solution

(i) and (ii) methods will form isopropylbenzene because n-propyl carbocation, being less stable, rearranges to the more stable (2°) isopropyl carbocation. Moreover, method (i) will lead to polyalkylation. Methods (iii) and (iv) can be used for preparing n-propylbenzene.

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