Which of the following nitro compounds are not soluble in NaOH ?

Question

Which of the following nitro compounds are not soluble in NaOH ? (A)  (CH3)3C⎯NO2  (B)  (CH3)2CH⎯NO2  (C)  CH3CH2⎯NO2  (D)  Ph⎯CH2⎯NO2

Tardigrade Admin · Accepted Answer

Nitro compounds having minimum one α- H, show tautomerism. Due to which their nitro group convert into acid group. In this acidic form, they dissolve in base. <img class="img-fluid question-image" alt="image" src="https://cdn.tardigrade.in/img/question/chemistry/92dd5dee952e9ca71a2a4159986c8dd7-.png" /> But nitro compounds having no α- H, do not show tautomerism. So, they cannot convert into acid form and thus, cannot dissolve in base.

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

$(C H_{3})_{3} C ⎯ N O_{2}$

$(C H_{3})_{2} C H ⎯ N O_{2}$

$C H_{3} C H_{2} ⎯ N O_{2}$

$P h ⎯ C H_{2} ⎯ N O_{2}$

Q. Which of the following nitro compounds are not soluble in NaOH ?

(CH3​)3​C⎯NO2​

(CH3​)2​CH⎯NO2​

CH3​CH2​⎯NO2​

Ph⎯CH2​⎯NO2​

Nitro compounds having minimum one α−H, show tautomerism. Due to which their nitro group convert into 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.

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

$(C H_{3})_{3} C ⎯ N O_{2}$

$(C H_{3})_{2} C H ⎯ N O_{2}$

$C H_{3} C H_{2} ⎯ N O_{2}$

$P h ⎯ C H_{2} ⎯ N O_{2}$