The alcohol having molecular formula $\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OH}$, when shaken with a mixture of anhydrous $\mathrm{ZnCl}_{2}$ and conc. HCl gives an oily layer product after five minutes. The alcohol is

• A

  $\mathrm{H}_{3} \mathrm{C}-\left(\mathrm{CH}_{2}\right)_{3}-\mathrm{OH}$
• B

  $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}_{1}$
• C

  $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{OH}$
• Correct answer
  D

  $\mathrm{H}_{3} \mathrm{C}-\mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2}-\mathrm{CH}_{3}$

Solution

Secondary alcohol, when shaken with a mixture of anthydrous $\mathrm{ZnCl}_{2}$ and conc. $\mathrm{HCl}$ (Lucas regent) gives an oily layer product after five minutes.
oily layer product after $5 \mathrm{~min}$. The amines in which amino group is directly attached to benzene ring undergo diazot isat ion reaction.

Hence, the correct answer is option: 'D'.