Question

Which of the following is not soluble in NaOH.
(1) CH3CH2--NO2
(2) (CH3)3C-NO2
(3) (CH3)2CH-NO,
(4) Ph-CH2 -NO2
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Answer 1

Answer:

I think option 1 ........

Answer 2

Explanation:

The base can take the α-H of the nitro-group, which will create a negative charge on that α-C, which can further delocalise with the Nitro-group (similar to Nitro-Acinitro tautomerism)

So, the whole compound will be in the state of a Resonance Hybrid where there will be partial double bond character between α-C,N and two O atoms.

YOU CAN NOTICE THAT THERE IS NO α-Hydrogen IN THE 2 COMPOUND AND HENCE NO RESONANCE STABILITY WOULD BE POSSIBLE FOR THE STRUCTURE .

HENCE , THE 2 IS THE ONLY COMPOUND WHICH WILL NOT BE SOLUBLE IN NaOH .

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