Q. The compound that reacts the fastest with sodium methoxide is

 2460  182 KCETKCET 2014Haloalkanes and Haloarenes Report Error

Solution:

The compound (where aryl, alkyl, or their derivatives on reaction with sodium methoxide (NaOMe) produces OMe and NaCl in accordance with following chemical equation

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The above reaction is a type of nucleophilic substitution reaction in which nucleophile [here OMe] replaces halogen atom of .

Reactivity of such organic halides in nucleophilic substitution reaction depends upon polarity of bond. Higher the polarity of bond easier will be the nucleophilic substitution reaction, hence, faster will be the reaction here bond in aryl halide has partially double bond character due to conjugation of lone pair of Cl with electrons of benzene ring as shown below

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Due to partial double bond character breaking of bond aryl halide become impossible. Among the given four substrates the compound having most polar bond will undergo faster nucleophilic substitution reaction. Greater the number of electron withdrawing group higher will be polarity of bond.

image Number of withdrawing groups

(a) has two electron withdrawing groups hence, (a) has most polar C - Cl bond and (a) will undergo fastest reaction chemical reaction occurring in the above reaction is as follows

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