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Topic: Why 3 equivalence of NaNH2 and not just 2 equivalence to get alkyne?  (Read 3144 times)

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Offline andy1111

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Why 3 equivalence of NaNH2 and not just 2 equivalence to get alkyne?
« on: May 07, 2012, 02:13:57 PM »
Hi Everyone,

Just working on some organic chemistry notes and I'm stuck on this 3 equivalence of NaNH2 vs just only 2. I mean if you start off with a vicinal dihalide and put in 2 equivalence of NanNH2 you will still get an alkyne. So, why the extra equivalence?

Thank you very much for your help in advance. :)
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Offline Dan

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Re: Why 3 equivalence of NaNH2 and not just 2 equivalence to get alkyne?
« Reply #1 on: May 07, 2012, 04:02:39 PM »
Is the product a terminal alkyne?
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Offline andy1111

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Re: Why 3 equivalence of NaNH2 and not just 2 equivalence to get alkyne?
« Reply #2 on: May 07, 2012, 06:22:41 PM »
Quote from: Dan on May 07, 2012, 04:02:39 PM
Is the product a terminal alkyne?

Can you explain to me why it would matter if it was a terminal alkyne compared to a internal alkyne?
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Offline orgopete

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Re: Why 3 equivalence of NaNH2 and not just 2 equivalence to get alkyne?
« Reply #3 on: May 07, 2012, 07:05:07 PM »
If the product were a terminal alkyne, would it compete in the elimination reaction?
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Offline Dan

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Re: Why 3 equivalence of NaNH2 and not just 2 equivalence to get alkyne?
« Reply #4 on: May 08, 2012, 04:18:34 AM »
Quote from: andy1111 on May 07, 2012, 06:22:41 PM
Quote from: Dan on May 07, 2012, 04:02:39 PM
Is the product a terminal alkyne?

Can you explain to me why it would matter if it was a terminal alkyne compared to a internal alkyne?

Compare the pKa of a terminal alkyne with that of ammonia.
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