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Biomolecules question

2022 · 28 Jul · Shift 2 · Q12
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Biomolecules question

2022 · 28 Jul · Shift 2 · Q12

JEE MainChemistryBiomoleculesMCQ+4 / −1
The formulas of A and B for the following reaction sequence JEE Main 2022 (Online) 28th July Evening Shift Chemistry - Biomolecules Question 70 English are
  1. A
    A=C7H14O8, B=C6H14\mathrm{A}=\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}_{8}, \quad \mathrm{~B}=\mathrm{C}_{6} \mathrm{H}_{14}A=C7​H14​O8​, B=C6​H14​
  2. B
    A=C7H13O7, B=C7H14O\mathrm{A}=\mathrm{C}_{7} \mathrm{H}_{13} \mathrm{O}_{7}, \quad \mathrm{~B}=\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}A=C7​H13​O7​, B=C7​H14​O
  3. C
    A=C7H12O8, B=C6H14\mathrm{A}=\mathrm{C}_{7} \mathrm{H}_{12} \mathrm{O}_{8}, \quad \mathrm{~B}=\mathrm{C}_{6} \mathrm{H}_{14}A=C7​H12​O8​, B=C6​H14​
  4. D
    A=C7H14O8, B=C6H14O6\mathrm{A}=\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}_{8}, \quad \mathrm{~B}=\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}_{6}A=C7​H14​O8​, B=C6​H14​O6​
View written solutionFree

Correct answer: A

  1. Identify the standard biomolecule reaction sequence

    In biomolecules, a very common sequence is:

    • glucose on treatment with HCN gives its cyanohydrin,
    • hydrolysis of the cyanohydrin gives a heptonic acid.

    Thus, if glucose has formula C6H12O6,\mathrm{C_6H_{12}O_6},C6​H12​O6​, then addition of HCN adds one carbon and leads ultimately to a compound with 7 carbons.

  2. Find the formula of A

    Start from glucose: C6H12O6\mathrm{C_6H_{12}O_6}C6​H12​O6​

    Cyanohydrin formation adds HCN across the aldehyde group. On hydrolysis of the nitrile group, we get a carboxylic acid. Net result is formation of a heptonic acid: C7H14O8\mathrm{C_7H_{14}O_8}C7​H14​O8​

    Check by structure logic:

    • one extra carbon is added,
    • aldehyde carbon becomes alcohol-bearing carbon in cyanohydrin,
    • nitrile hydrolyzes to carboxylic acid,
    • total oxygens become 8.

    So, A=C7H14O8A = \mathrm{C_7H_{14}O_8}A=C7​H14​O8​

  3. Find the formula of B

    In the Kiliani–Fischer type sequence, after chain extension and suitable reduction/deoxygenation considerations in carbohydrate chemistry, the hydrocarbon obtained corresponding to the carbon chain is n-hexane.

    Formula of hexane is: C6H14\mathrm{C_6H_{14}}C6​H14​

    Hence, B=C6H14B = \mathrm{C_6H_{14}}B=C6​H14​

  4. Match with options

    The pair obtained is: A=C7H14O8,B=C6H14A = \mathrm{C_7H_{14}O_8}, \quad B = \mathrm{C_6H_{14}}A=C7​H14​O8​,B=C6​H14​

    This matches Option A.

  5. Verification with stored answer

    Stored correct answer is A.

    My derived answer is also A, so they agree.

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