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Question

CH2|ClOH is more acidic than CH2|NO2CH2OH


A

True

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B

False

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Solution

The correct option is A

True


Whenever there is a difference in the distance between two electronegative groups, the intensity of effect decreases when the distance from the source increases.

The acidity of effect alcohols depends on the stability of alkoxide ion (i.e., the conjugate base of alcohol) which is obtained by the dissociation of alcohols.

ROHRO+H

Acid strength of alcohol α stability of alkoxide ion

The stability of the alkoxide ion depends on the -I effect of the group attached. -I effect stabilises the alkoxide ion as a result of the reduction in charge density on the oxygen atom.

In our case, -I effect of Cl is greater because of its proximity as we discussed.

CH2|ClOH CH2|NO2CH2OH

I is more acidic than II even though the -I effect of NO2 is higher.


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