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Biomolecules question

2022 · 27 Jun · Shift 1 · Q10
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Biomolecules question

2022 · 27 Jun · Shift 1 · Q10

JEE MainChemistryBiomoleculesMCQ+4 / −1
L-isomer of a compound 'A' (C4H8O4C_4H_8O_4C4​H8​O4​) gives a positive test with [Ag(NH3)2]+[Ag(NH_3)_2]^+[Ag(NH3​)2​]+. Treatment of 'A' with acetic anhydride yields triacetate derivative. Compound 'A' produces an optically active compound (B) and an optically inactive compound (C) on treatment with bromine water and HNO3HNO_3HNO3​ respectively. Compound (A) is :
  1. A
    JEE Main 2022 (Online) 27th June Morning Shift Chemistry - Biomolecules Question 84 English Option 1
  2. B
    JEE Main 2022 (Online) 27th June Morning Shift Chemistry - Biomolecules Question 84 English Option 2
  3. C
    JEE Main 2022 (Online) 27th June Morning Shift Chemistry - Biomolecules Question 84 English Option 3
  4. D
    JEE Main 2022 (Online) 27th June Morning Shift Chemistry - Biomolecules Question 84 English Option 4
View written solutionFree

Correct answer: A

  1. Given molecular formula and Tollens' test
    Compound AAA has formula C4H8O4C_4H_8O_4C4​H8​O4​ and gives a positive test with [Ag(NH3)2]+[Ag(NH_3)_2]^+[Ag(NH3​)2​]+.
    Hence, AAA must contain an aldehyde group.

  2. Triacetate formation with acetic anhydride
    On treatment with acetic anhydride, AAA gives a triacetate derivative.
    This means AAA contains three hydroxyl groups that can be acetylated.

  3. Possible nature of AAA
    With one aldehyde group and three −OH-OH−OH groups in a four-carbon compound, AAA must be an aldo-tetrose: CHO−CH(OH)−CH(OH)−CH2OHCHO-CH(OH)-CH(OH)-CH_2OHCHO−CH(OH)−CH(OH)−CH2​OH This matches C4H8O4C_4H_8O_4C4​H8​O4​.

  4. Given that the L-isomer of AAA is considered
    Among aldotetroses, the possibilities are:

    • erythrose
    • threose
  5. Reaction with bromine water
    Bromine water oxidizes the aldehyde group to a carboxylic acid, giving an aldonic acid.
    The product BBB is said to be optically active.

  6. Reaction with HNO3HNO_3HNO3​
    Nitric acid oxidizes both terminal groups:

    • CHO→COOHCHO \to COOHCHO→COOH
    • CH2OH→COOHCH_2OH \to COOHCH2​OH→COOH

    So the product becomes a dicarboxylic acid: HOOC−CH(OH)−CH(OH)−COOHHOOC-CH(OH)-CH(OH)-COOHHOOC−CH(OH)−CH(OH)−COOH

    Product CCC is said to be optically inactive.

  7. Identify which aldotetrose gives meso tartaric acid on oxidation
    Oxidation of erythrose gives: HOOC−CH(OH)−CH(OH)−COOHHOOC-CH(OH)-CH(OH)-COOHHOOC−CH(OH)−CH(OH)−COOH with the two middle OHOHOH groups on the same side in Fischer projection for one enantiomeric series, which corresponds to meso tartaric acid after considering symmetry. Hence it is optically inactive.

    Oxidation of threose gives an optically active tartaric acid, not inactive.

    Therefore, AAA must be erythrose.

  8. Check consistency with bromine water product
    Oxidation of erythrose with bromine water gives erythronic acid, which remains optically active, matching the statement about BBB.

  9. Conclusion
    Therefore, compound AAA is L-erythrose (or simply erythrose as the compound type).

  10. Comparison with stored answer
    The stored correct answer is A, and this matches the identified compound.

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