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Question 105 of 110

Q.What happens when D-glucose is treated with the following reagents? (1+1=2)

(a) HI
(b) Conc. HNO3HNO_3
Yanam CbseCBSE Class XII Board 2024Subjective· 2mImportance★★★★★
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When D-glucose is treated with HI, it undergoes complete reduction to n-hexane; with concentrated HNO3HNO_3, it undergoes oxidation of both terminal groups to form saccharic acid.

D-glucose is an aldohexose, meaning it is a six-carbon sugar with an aldehyde group (−CHO-\text{CHO}) at one end and multiple hydroxyl groups (−OH-\text{OH}). While glucose primarily exists in cyclic hemiacetal forms in solution, its reactions with strong reagents like HI and concentrated HNO3HNO_3 often proceed via its open-chain form, where the functional groups are fully exposed. The nature of the reagent dictates whether the functional groups are reduced or oxidized.

(a) Reaction with HI

  1. Understanding the Reagent: Hydrogen iodide (HI), especially when heated, is a very strong reducing agent. It is capable of reducing not only aldehyde groups but also all hydroxyl groups present in an organic molecule.
  2. Structure of D-Glucose: In its open-chain form, D-glucose has an aldehyde group at carbon C1 and five hydroxyl groups. One of these is a primary alcohol group at C6, and the other four are secondary alcohol groups at C2-C5.

CHO∣CHOH∣CHOH∣CHOH∣CHOH∣CH2OH\begin{array}{c} \text{CHO} \\ | \\ \text{CHOH} \\ | \\ \text{CHOH} \\ | \\ \text{CHOH} \\ | \\ \text{CHOH} \\ | \\ \text{CH}_2\text{OH} \\ \end{array}

  1. The Reduction Process: When D-glucose is heated with HI, all the oxygen-containing functional groups are completely removed. The aldehyde group (−CHO-\text{CHO}) is reduced to a methyl group (−CH3-\text{CH}_3), and all the hydroxyl groups (−OH-\text{OH}) are reduced to hydrogen atoms (−H-\text{H}). This process effectively deoxygenates the molecule, leaving behind a straight-chain alkane.
  2. Product Formation: Since D-glucose has a six-carbon straight chain, the complete reduction yields n-hexane. This reaction is historically significant as it provided crucial evidence for the straight-chain structure of glucose.

C6H12O6→HI, ΔCH3CH2CH2CH2CH2CH3(n-hexane)\text{C}_6\text{H}_{12}\text{O}_6 \xrightarrow{\text{HI, } \Delta} \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_3 \quad (\text{n-hexane})

Watch out

This is a complete reduction. Milder reducing agents, such as NaBH4\text{NaBH}_4, would only reduce the aldehyde group to a primary alcohol, forming sorbitol, leaving the other hydroxyl groups untouched. HI is powerful enough to remove all oxygen atoms.

(b) Reaction with Conc. HNO3HNO_3

  1. Understanding the Reagent: Concentrated nitric acid (HNO3HNO_3) is a strong oxidizing agent. It is capable of oxidizing both aldehyde groups and primary alcohol groups to carboxylic acid groups (−COOH-\text{COOH}). Secondary alcohol groups are generally resistant to oxidation by concentrated HNO3HNO_3 under these conditions.
  2. Structure of D-Glucose: As discussed, D-glucose has an aldehyde group at C1 and a primary alcohol group at C6. …

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