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Topic: chloroacetat reactivity  (Read 1902 times)

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Offline perivar

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chloroacetat reactivity
« on: October 17, 2012, 10:14:13 AM »
Why is etyl 2 - chloroacetat more reactive towards ammonia than etyl acetat?
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Offline Dan

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Re: chloroacetat reactivity
« Reply #1 on: October 17, 2012, 10:39:19 AM »
Ammonia is a nucleophile (and a base), so it reacts with electrophiles (and acids).

Do you have any ideas about why ethyl 2-chloroacetate might be more electrophilic (or acidic) than ethyl acetate?
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Offline perivar

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Re: chloroacetat reactivity
« Reply #2 on: October 17, 2012, 11:48:55 AM »
Quote from: Dan on October 17, 2012, 10:39:19 AM
Ammonia is a nucleophile (and a base), so it reacts with electrophiles (and acids).

Do you have any ideas about why ethyl 2-chloroacetate might be more electrophilic (or acidic) than ethyl acetate?

Hello, is it because chloro draws electrons from the carbon atom in the carbonyl - group making it a stronger electrophile?
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Offline Dan

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Re: chloroacetat reactivity
« Reply #3 on: October 17, 2012, 11:56:34 AM »
Yes, keyword: Inductive effect.
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