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Topic: Reactivity with hydroxide ion  (Read 3300 times)

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Offline LHM

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Reactivity with hydroxide ion
« on: January 08, 2011, 08:48:23 PM »
Why is (CH3)3CBr more likely to react with OH- than (CH3)3CCl? I think it has to do with electronegativity, but isn't Cl more electronegative so it's more likely to take the electrons from the C atom it's attached to and create a partial positive charge over that C?
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Offline Schrödinger

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Re: Reactivity with hydroxide ion
« Reply #1 on: January 09, 2011, 12:15:05 AM »
This is a substitution reaction, and the intermediate formed is a carbocation.
http://en.wikipedia.org/wiki/SN1_reaction

Br is a better leaving group than Cl, and since formation of the carbocation is the Rate Determining Step, (CH3)3CBr is more likely to react with OH- than (CH3)3CCl.
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Offline LHM

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Re: Reactivity with hydroxide ion
« Reply #2 on: January 09, 2011, 11:11:49 AM »
But what makes Br a better leaving group than Cl?
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Offline Schrödinger

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Re: Reactivity with hydroxide ion
« Reply #3 on: January 10, 2011, 10:47:37 AM »
C-Br bond is weaker than the C-Cl bond
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