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  • Mark the correct increasing order of reactivity of the following compounds with HBr/HCl.

Mark the correct increasing order of reactivity of the following compounds with HBr/HCl.

(i) a < b < c

(ii) b < a < c

(iii) b < c < a

(iv) c < b < a

Answers (1)

The answer is the option (iii). The type of reaction taking place in this process is the nucleophilic substitution reaction. The mechanism followed is S_{N}1, so the first slow step of the mechanism involves the formation of carbocation that determines the rate of reaction and then the addition of a nucleophile. The carbocation formed also controls the reactivity of this product formed. But in case of the presence of a highly electron-withdrawing group (-NO_{2}), the carbocation will be destabilised, and the reaction will not be favoured.

Whereas the high electron-withdrawing nature of the (-Cl) group due to lone pair presence, its tendency of electron-withdrawing is slightly low than (-NO_{2}), it will also manage to destabilise the carbocation and do not favour the reaction.

In the case of the first compound, C_{6}H_{5}CH_{2}OH, the absence of any destabilising factors makes the reaction occurrence favourable. Thus, the concluded increasing order of reactivity will be Option (iii) b < c < a

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