Question Details

In the following reaction sequence, the major product Q is

Options

A

B

C

D

Show Answer

Correct Answer :

Option D

Option 4

Solution :

The correct option is Option 4.

Let's break down the reaction sequence step-by-step to determine the identity of the major product Q:

Step 1: Conversion of L-Glucose to Benzene (P)
When L-glucose is heated with concentrated hydrogen iodide (HI), it undergoes complete reduction of all hydroxyl groups and the carbonyl group to yield n-hexane as the major hydrocarbon product:

L-GlucoseHI, ΔCH3CH2CH2CH2CH2CH3 (n-hexane)

When n-hexane is treated with chromium oxide (Cr2O3) at 775 K under 10–20 atm pressure, it undergoes dehydrogenation and cyclization (aromatization) to form benzene:

C6H14Cr2O3, 775 K, 10-20 atmC6H6 (Benzene, P)+4H2

Step 2: Free Radical Addition to form Product Q
When benzene (P) is reacted with excess chlorine (Cl2) in the presence of ultraviolet (UV) light, it undergoes a free-radical addition reaction rather than substitution. The three conjugated double bonds in the benzene ring add three molecules of chlorine to produce 1,2,3,4,5,6-hexachlorocyclohexane (commonly known as benzene hexachloride, BHC, Lindane, or Gammaxene):

C6H6+3Cl2UV (excess)C6H6Cl6 (Q)

The chemical structure of this addition product, 1,2,3,4,5,6-hexachlorocyclohexane, has chlorine atoms attached to all six carbons of a saturated cyclohexane ring, which corresponds precisely to the structure shown in Option 4.

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