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Arrange the following compounds in increasing order of S_(N)1 reactivity. (i) ClCH_(2)CH = CHCH_(2)CH_(3), CH_(3)C(Cl) = CHCH_(2)CH_(3), CH_(3)CH = CHCH_(2)CH_(2)Cl , CH_(3)CH = CHCH(Cl)CH_(3) (ii) CH_(3)CH_(2)Br, CH_(2) = CHCH(Br)CH_(3), CH_(2) = CHBr, CH_(3)CH(Br)CH_(3) (iii) (CH_(3))_(3)C Cl , C_(6)H_(5)C(CH_(3))_(2)Cl , (CH_(3))_(2)CHCl , CH_(3)CH_(2)CH_(2)Cl |
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Answer» Solution :The REACTIVITY for Spi reactivity follows the order : `(i) CH_(3) - underset(I)underset(Cl)underset(|)C = CH - CH_(2) - CH_(3) lt CH_(3) - CH = underset(II) (CH - CH_(2) - CH_(2)Cl)lt ClCH_(2) - CH = underset(III) CH - CH_(2) - CH_(3)lt CH_(3) - CH = CH - underset(IV)underset(Cl)underset(|)CH - CH_(3) ` IVshows maximum reactivity because the carbocation is stabilised by resonance (CONJUGATION from double bond). I is least reactive because the carbocation is least stable, being linked to double bond directly. (ii) `CH_(2) = CHBr lt CH_(3)CH_(2)Br lt CH_(3) - underset(Br)underset(|)CH - CH_(3) lt CH_(3) = CH - underset(Br)underset(|)CH - CH_(3) ` This is againbased upon the STABILITY of the carbocation . (iii) `CH_(3)CH_(2)CH_(2)Cl lt (CH_(3))_(2)Cl lt (CH_(3))_(2)CHCl lt (CH_(3))_(3) C Cl lt C_(6)H_(5) - underset(CH_(3))underset(|)overset(Cl)overset(|)C - CH_(3)` The carbocation from `C_(6)H_(5)C(CH_(3))_(2)Cl ` is stabilised to the maximum extent. |
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