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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: Grignard reagent
Forum Index -> Organic Chemistry like the article? email it to a friend.  
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srujana (3045)

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Which of the following reactions are not possible and why?
 
Grignard reagent with
1.R'-CC-H
2.R'-CC-R''
3.R-CH=CH2
What is meant by acidic hydrogen?

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karthik2007 (3349)

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edited - yeah, 2 shud be right.... I was having a doubt bet 1 and 2... and john has cleared it. In 2, the carbon is not sufficiently positively charged due to the presence of bulky alkyl groups.

Will nip in at times to solve problems :)
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johri_anshuman (1176)

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i think that the reaction in case 2 is not possible

here in case 2nd the necessary polarity for the reaction to occur is not available...

any hydrogen which is available in the form oh H+ is acidic hydrogen

in R-C(triple bond)C-H

the H is acidic hydrogen... because of the high polarity of the C-H bond this hydrogen is also available as H+ when reqd...

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srujana (3045)

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It has been given that even reaction 3 is not possible......dont know the reason though..........is it something related to stearic hinderance?

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johri_anshuman (1176)

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The very same reason applies to case 3 also...

Grignard reagent RMgX breaks as R-  and +MgX

so the reaction takes place only when the reactant is sufficiently polar.

the polarity of double bond is much less than  --C(triple bond)C-- or C=O and so the reaction will not take place...

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srujana (3045)

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Then what about the reaction with a compound like R-CH3.....is it possible?

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johri_anshuman (1176)

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such a compound cannot react with GR...

i dont think it is possible...

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