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Topic: Why amine group attack and not hydroxyl?  (Read 1209 times)

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Offline JoeyBob

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Why amine group attack and not hydroxyl?
« on: March 18, 2020, 09:05:56 PM »
??? Isn't O a better electrophile than N?
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ch3mist

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Re: Why amine group attack and not hydroxyl?
« Reply #1 on: March 18, 2020, 09:51:51 PM »
The NH2 is a better nucleophile than the OH.
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Offline JoeyBob

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Re: Why amine group attack and not hydroxyl?
« Reply #2 on: March 19, 2020, 01:23:10 AM »
Quote from: ch3mist on March 18, 2020, 09:51:51 PM
The NH2 is a better nucleophile than the OH.

How?
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Offline rolnor

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Re: Why amine group attack and not hydroxyl?
« Reply #3 on: March 19, 2020, 09:32:18 AM »
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Offline hollytara

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Re: Why amine group attack and not hydroxyl?
« Reply #4 on: March 19, 2020, 02:08:49 PM »
Nucleophilicity is inversely correlated to electronegativity.  So N lone pairs react faster than O lone pairs - the N is more willing to share, being less electronegative. 
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