Which of the following sequences of rate of alkaline hydrolysis of esters is correct :

C H_{3} C H_{2} C O O C H_{3} < (C H_{3})_{2} C H C O O C H_{3} < (C H_{3})_{3} C C O O C H_{3}

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C H_{3} C H_{2} C O O C H_{3} > (C H_{3})_{2} C H C O O C H_{3} > (C H_{3})_{3} C C O O C H_{3}

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C H_{3} C H_{2} C O O C H_{3} > (C H_{3})_{2} C H C O O C H_{3} < (C H_{3})_{3} C C O O C H_{3}

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C H_{3} C H_{2} C O O C H_{3} < (C H_{3})_{2} C H C O O C H_{3} > (C H_{3})_{3} C C O O C H_{3}

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Solution

The correct option is B $C H_{3} C H_{2} C O O C H_{3} > (C H_{3})_{2} C H C O O C H_{3} > (C H_{3})_{3} C C O O C H_{3}$
The hydroxide nucleophiles attack at the electrophilic $C$ of the ester $C = O$ , break the $p i$ bond and create a tetrahedral intermediate. Esters with more electrophilic $C O$ would be more reactive. The increasing inductive effect decreases the electrophilc character of $C O$ , therefore the order of rate of alkaline hydrolysis of esters is $C H_{3} C H_{2} C O O C H_{3} > (C H_{3})_{2} C H C O O C H_{3} > (C H_{3})_{3} C C O O C H_{3}$

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Similar questions

C H_{3} C H_{2} C O N H_{2}

C H_{3} C H_{2} C O O C H_{3}

C H_{3} C H_{2} C O C l

List I	List II
(Compounds)	(Reactions)
(a) $C H_{3} (C H_{2})_{3} N H_{2}$	(i) Alkaline hydrolysis
(b) $C H_{3} C \equiv C H$	(ii) With $K O H$ (alcohol) and $C H C l_{3}$ produces bad smell
(c) $C H_{3} C H_{2} C O O C H_{3}$	(iii) Gives white ppt. with ammoniacal $A g N O_{3}$
(d) $C H_{3} C H (O H) C H_{3}$	(iv) With Lucas reagent cloudiness appears after 5 minutes

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