Which of the following nitro compounds are not soluble in $N a O H$ ?

{({C H}_{3})}_{3} C - {N O}_{2}

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{({C H}_{3})}_{3} C H - {N O}_{2}

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{C H}_{3} {C H}_{2} - {N O}_{2}

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P h - {C H}_{2} - {N O}_{2}

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Solution

The correct option is B ${({C H}_{3})}_{3} C - {N O}_{2}$
Nitro compounds having a minimum of $α - H$ show tautomerism. Due to which their nitro group converts into the acid group. In this acidic form, they dissolve in base.
But nitro compounds having no $α - H$ do not show tautomerism. So, they cannot convert into acid form and thus, cannot dissolve in base.

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