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Organic Chemistry

Blazing goIITian

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26 Jun 2008 14:43:20 IST

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708

GIve the product of the reaction.

None

GIve the product of the reaction.

CH3-NO2 + -----> ?

Also tell the intermediate and show the mechanism.

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Comments (13)

sohraan

Blazing goIITian

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26 Jun 2008 14:47:21 IST

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i think the base will accept proton since the compound is acidic (due to no2 grp)

so product will be

ch2-no2(with a negative sign) and BH

CORRECT ME IF AM WRONG

U V

Blazing goIITian

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26 Jun 2008 14:52:23 IST

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So, what will be the intermediate here?

sohraan

Blazing goIITian

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26 Jun 2008 14:59:24 IST

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CH2NO2(WITH A NEGATIVE SIGN WILL BE INTERMEDIATE)

U V

Blazing goIITian

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26 Jun 2008 21:50:08 IST

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Options are:

Carbocation

Carbonanion - not the answer

Carbene

OR something like that.

iberis

Hot goIITian

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26 Jun 2008 22:37:39 IST

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Just like aldehydes and ketones, the alpha-hydrogen of nitro compounds are also acidic. So treatment with a base will lead to formation of a resonance stabilized carbanion..

Gaurav Sood

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26 Jun 2008 23:15:32 IST

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i think that ch3-B will be formed bu sn2 reaction as hno2 is a good leaving group... a transition state will be formed and then hno2 will leave.

Gaurav Sood

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26 Jun 2008 23:15:50 IST

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U V

Blazing goIITian

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27 Jun 2008 22:10:53 IST

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Nup, the carbonanion is not the answer.

Gaurav Sood

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27 Jun 2008 22:20:49 IST

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is it a transition state then??

U V

Blazing goIITian

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27 Jun 2008 22:25:20 IST

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nup, neither transition state.

The answer is Carbocation.

gaurang

Cool goIITian

Joined: 27 Jun 2008

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27 Jun 2008 22:31:52 IST

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the product will be CH3B and NO2 with a negative charge..

the mechanism would be sn2

n the intermidiate wiil be a partial bond between B and C and C would have delta positive charge as electrons would be attracted NO2 as it will be leavin group...

correct me if im wrong

Gaurav Sood

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27 Jun 2008 22:33:54 IST

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but primary amines do not favour an sn1 reaction. the carbocation will not be stable at all (primary carbocation)... am i wrong there??

U V

Blazing goIITian

Joined: 26 Oct 2007

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28 Jun 2008 22:26:16 IST

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oh yup.
Your right.

Thanks

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