JEE Main 2022 · 27 July · evening · Single correct · +4 / −1

Match List - I with Match List - II.
Choose the correct answer from the options given below:

List - IList - II
(A)Glucose + HI(I)Gluconic acid
(B)Glucose + Br₂ water(II)Glucose pentacetate
(C)Glucose + acetic anhydride(III)Saccharic acid
(D)Glucose + HNO₃(IV)Hexane
  1. (a) (A) - (IV), (B) - (I), (C) -(II), (D) - (III)
  2. (b) (A) - (IV), (B) - (III), (C) -(II), (D) - (I)
  3. (c) (A) - (III), (B) - (I), (C) -(IV), (D) - (II)
  4. (d) (A) - (I), (B) - (III), (C) -(IV), (D) - (II)
Answer and solution

Answer (a) (A) - (IV), (B) - (I), (C) -(II), (D) - (III)

Solution

Chemistry ma’am · 3 steps

Ask what each reagent touches: HI strips every oxygen, bromine water one end, nitric acid both ends.

  1. HI reduces fully. Prolonged heating with HI removes every oxygen from glucose and gives n-hexane. This shows that the six carbons sit in one straight chain. So A matches IV.
  2. Two oxidisers. Bromine water is a mild oxidiser. It oxidises only the -CHO group to -COOH, giving gluconic acid. Nitric acid is strong and also oxidises the terminal -CH₂OH, giving the dicarboxylic saccharic acid, so B matches I and D matches III.
    ReactionWhat changesProduct
    (A) Glucose + HIall oxygens removed(IV) hexane
    (B) Glucose + Br₂ wateronly -CHO becomes -COOH(I) gluconic acid
    (C) Glucose + acetic anhydrideall five -OH groups acetylated(II) glucose pentaacetate
    (D) Glucose + HNO₃-CHO and -CH₂OH both become -COOH(III) saccharic acid
  3. So. The matching is A-IV, B-I, C-II, D-III, which is option (a).

The idea to keep. Bromine water oxidises only the aldehyde end and gives a monoacid. Nitric acid oxidises both ends and gives a diacid. HI goes the other way and reduces glucose all the way to hexane.

Answer from the NTA final answer key. Solution by PrepWiser.

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Asked about 150 times in JEE Main since 2020. This question is from 2022.