Which of the following compounds will react with two moles of ${C H}_{3} M g B r$ ?

C_{2} H_{5} C O O H

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{C H}_{3} C O O H

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{C H}_{3} C \equiv C C H_{3}

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H C \equiv C - {C H}_{2} O H

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Solution

The correct option is D $H C \equiv C - {C H}_{2} O H$
Reaction of carboxylic acid with Grignard is shown above. It'll only consume 1 mole of $C H_{3} M g B r$ .

$C H_{3} C \equiv C C H_{3}$ won't react with Grignard reagent because it doesn't have active H-atom.

In $H C \equiv C - {C H}_{2} O H$ two active hydrogen atoms are present, hence it will react with two moles of ${C H}_{3} M g B r$ (Grignard reagent) as shown below.

$H C \equiv C - {C H}_{2} O H + 2 {C H}_{3} M g B r ⟶ 2 {C H}_{4} + B r M g C \equiv C C H_{2} O M g B r$

Option D is the correct answer.

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