JEE Main · 2022 · Shift-IImediumBIO-033

The formulas of A and B for the following reaction sequence are

Biomolecules · Class 12 · JEE Main Previous Year Question

Question

The formulas of A and B for the following reaction sequence are image

Options
  1. a

    A=\ceC7H14O8, B=\ceC6H14\text{A} = \ce{C7H14O8},\ \text{B} = \ce{C6H14}

  2. b

    A=\ceC7H13O7, B=\ceC7H14O\text{A} = \ce{C7H13O7},\ \text{B} = \ce{C7H14O}

  3. c

    A=\ceC7H12O8, B=\ceC6H14\text{A} = \ce{C7H12O8},\ \text{B} = \ce{C6H14}

  4. d

    A=\ceC7H14O8, B=\ceC6H14O6\text{A} = \ce{C7H14O8},\ \text{B} = \ce{C6H14O6}

Correct Answera

A=\ceC7H14O8, B=\ceC6H14\text{A} = \ce{C7H14O8},\ \text{B} = \ce{C6H14}

Detailed Solution

Step 1: Cyanohydrin Addition — Reaction of glucose (C6H12O6C_6H_{12}O_6) with \ceHCN\ce{HCN} adds one carbon atom, forming a cyanohydrin with the formula C7H13O6NC_7H_{13}O_6N.

Step 2: Hydrolysis — Subsequent hydrolysis of the nitrile group (\ceCN\ce{-CN}) to a carboxylic acid (\ceCOOH\ce{-COOH}) results in a hydroxy acid 'A' with the formula C7H14O8C_7H_{14}O_8.

Step 3: Reduction — Treatment with \ceHI\ce{HI} and red phosphorus reduces the hydroxy groups to a straight-chain hydrocarbon. The resulting product is n-heptane or a related reduced structure. Matching 'A' as C7H14O8C_7H_{14}O_8 identified the correct option.

Key Point: This Kiliani-Fischer-like sequence confirms the presence of an aldehyde and a straight six-carbon chain in glucose.

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