Organic Chemistry> ethanol + HBr -----> ethylbromide + water...

ethanol + HBr -----> ethylbromide + water please give mechanism this question came in cbse 2014 exam

SIDDHARTH CHANDRASEKARAN , 11 Years ago

Grade 12th pass

3 Answers

Ruchi Shaw

Last Activity: 11 Years ago

When treated with HBr,ethanol goes a nucleophilic substitution reaction to generate ethylbromide and water.Reaction usually proceeds via SN1 mechanism which proceeds via a carbocation intermediate that can also undergo rearrangement.

Mechanism:

Step 1 ) An acid base reaction takes place,Protonation of the alcoholic oxygen takes place to make it a better leaving group. This step is very fast and reversible. The lone pairs on the oxygen make it a Lewis base.

Step 2) Cleavage of the C-O bond allows the loss of the good leaving group, a neutral water molecule to give a carbocation intermediate.This is the rate determining step (bond breaking is intermediate)

Step 3 ) Attack of the nucleophilic bromide ion on the elctrophilic carbocations create ethylbromide.

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Ruchi Shaw

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So if do it

Last Activity: 3 Years ago

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Sachin D

Last Activity: 3 Years ago

It is an SN1 mechanism. SN1 reaction mechanism follows a step-by-step process wherein first, the carbocation is formed from the removal of the leaving group. Then the carbocation is attacked by the nucleophile.