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Question -

How will you convert benzene into (i)p-nitrobromobenzene (ii) m-nitrochlorobenzene (iii) p-nitrotoluene (iv) acetophenone?



Answer -

(i)The two substituents in the benzene ring are present at p-positions. Therefore,the sequence of reactions should be such that first an o, p-directing group,i.e., Br atom should be introduced in the benzene ring and this should befollowed by nitration. Thus,

(ii) Here since the two substituents are at p-position w.r.t. each other,therefore, the first substituent in the benzene ring should be a o, p-directinggroup (i.e., CH3) and then the other group (i.e., NO2)should be introduced. Therefore, the sequence of reactions is:

(iii)Here since the two substituents are at m-position w.r.t. each other,therefore, the first substituent in the benzene ring should be a m-directinggroup (i.e., NO2) and then other group (i.e.,Cl) should beintroduced.

(iv)Acetophenone can be prepared by F.C. acylation using either acetyl chlorideor acetic anhydride.

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