JEE Challenger
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Identify Chemical Structure of Cellulose Triacetate

Cellulose upon acetylation with excess acetic anhydride/H2SO4\text{H}_2\text{SO}_4 (catalytic) gives cellulose triacetate whose structure is

Options

A
Option A Diagram 1
Correct
B
Option B Diagram 1
C
Option C Diagram 1
D
Option D Diagram 1

Topics & Concepts

Step-by-Step Solution

To determine the correct chemical structure of cellulose triacetate, we analyze the structure of cellulose and the effect of complete acetylation:

  1. Structure of Cellulose:
    Cellulose is a linear polymer composed of D\text{D}-glucose monomeric units joined by β(1→4)\beta(1 \to 4)-glycosidic linkages.
    Due to the geometry of the β(1→4)\beta(1 \to 4) linkage, adjacent glucose units are flipped by 180∘180^\circ relative to one another along the polymer chain to maintain a linear, extended ribbon-like conformation.

  2. Acetylation Reaction:
    Each D\text{D}-glucose unit in cellulose contains three free hydroxyl (-OH\text{-OH}) groups:

    • Secondary -OH\text{-OH} groups at C-2\text{C-2} and C-3\text{C-3}
    • Primary -OH\text{-OH} group at C-6\text{C-6} (in the -CH2OH\text{-CH}_2\text{OH} group attached to C-5\text{C-5})

    When cellulose is treated with excess acetic anhydride in the presence of a catalytic amount of H2SO4\text{H}_2\text{SO}_4, all three -OH\text{-OH} groups per monomer unit undergo acetylation to form acetoxy (-OAc\text{-OAc}) groups:
    Cellulose-OH+(CH3CO)2O→H2SO4Cellulose-OAc+CH3COOH\text{Cellulose-OH} + (\text{CH}_3\text{CO})_2\text{O} \xrightarrow{\text{H}_2\text{SO}_4} \text{Cellulose-OAc} + \text{CH}_3\text{COOH}

  3. Comparison of the Options:

    • Structure (A) correctly depicts the alternating inverted pyranose rings characteristic of the β(1→4)\beta(1 \to 4)-glycosidic linkages of cellulose, with complete acetylation at positions C-2\text{C-2}, C-3\text{C-3}, and C-6\text{C-6} (-CH2OAc\text{-CH}_2\text{OAc}).
    • Structure (B) contains unreacted -OH\text{-OH} groups at C-2\text{C-2} and C-3\text{C-3}, representing incomplete acetylation.
    • Structures (C) and (D) show non-inverted pyranose rings aligned in the same direction, which corresponds to α(1→4)\alpha(1 \to 4)-glycosidic linkages found in amylose (starch) rather than cellulose.

Thus, structure (A) correctly represents cellulose triacetate.

Correct Answer: A