Question

The structure of the product 'Z' in the reaction sequence is: \[ \text{CHO} \] \[ \mid \] \[

• A. Chlorobenzene
• B. 1,2-Dichlorobenzene
• C. Hexachlorobenzene
• D. 1,2,3,4,5,6-Hexachlorocyclohexane (Gamma-Hexachlorocyclohexane or Lindane)

Hint:

In high-pressure chlorination, benzene undergoes full substitution, forming hexachlorobenzene.

Answer 1

The Correct Option is C

Step 1: Identifying the Initial Compound The given compound (CHOH\(_4\)CH\(_2\)OH) represents glucose or sorbitol, which undergoes reduction with HI and heat to form cyclohexane (X). Step 2: Oxidation to Benzene Cyclohexane (X) undergoes dehydrogenation with \( Cr_2O_3 \) at high temperatures (773 K), resulting in benzene (Y). Step 3: Chlorination Benzene (Y) reacts with chlorine (\( Cl_2 \)) under high pressure (10-20 atm) and UV light, leading to the formation of hexachlorobenzene (Z). Conclusion Thus, the correct answer is: \[ \text{Hexachlorobenzene} \]