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Topic: Is this Correct?  (Read 3467 times)

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Offline w451208

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Is this Correct?
« on: October 17, 2010, 10:25:44 PM »

Offline majorjp

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Re: Is this Correct?
« Reply #1 on: October 17, 2010, 10:57:41 PM »
Essentially yes, this is a reaction with a Grignard reagent and a terminal alkyne. In this case the sp hybridization of the C-C triple bond makes the teminal hydrogen quite acidic therefore the acidic hydrogen would attack the Gringnard reagents nucleophilic R-group to form ethane, leaving a negative charge on the alkyne and a postive charge on the Mg-Br complex.

Offline w451208

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Re: Is this Correct?
« Reply #2 on: October 17, 2010, 11:25:59 PM »
Thanks for your help. Could you help me with this one as well. Why cant the answer be B?


Offline orgopete

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Re: Is this Correct?
« Reply #3 on: October 20, 2010, 09:06:02 AM »
I see you are having a problem understanding the curved arrow convention. Try printing out and doing the problems here:
http://www.curvedarrowpress.com/agocm/inside/sampler/sampler.html
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline karlosshughes

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Re: Is this Correct?
« Reply #4 on: October 27, 2010, 01:15:39 AM »
Thanks for your help. Could you help me with this one as well. Why cant the answer be B?



Because amines are not electrophilic. Enolates are nucleophilic on carbon and these will react with electrophilic species, such as carbonyl compounds but not amines. The nitrogen already has a full octet and so can't accept any more electrons, which is what would happen if the double bond attacked the nitrogen.
Chemistry student & organic kid.
Dabbles in other chemistry too (but only because I have to XD).

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