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Question 108 of 110

Q.Give the plausible explanation for the following:

(a) Glucose doesn't give 2,4-DNP test.
(b) The two strands in DNA are not identical but are complementary.
(c) Starch and cellulose both contain glucose unit as monomer, yet they are structurally different.
Uttar Pradesh UpmspCBSE Class XII Board 2020Subjective· 3mImportance★★★★★
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(a) Glucose exists predominantly as a cyclic hemiacetal, not as a free aldehyde, so it cannot react with 2,4-DNP. (b) DNA strands are complementary because A pairs with T and G pairs with C through specific hydrogen bonding, not identical sequences. (c) Starch has α-glycosidic linkages (digestible, helical) while cellulose has β-linkages (linear, rigid fibers).


(a) Why glucose doesn't give the 2,4-DNP test

The 2,4-dinitrophenylhydrazine (2,4-DNP) test is a classic carbonyl test. It detects free aldehyde or ketone groups by forming a yellow-to-orange precipitate (a hydrazone). The question is: glucose is an aldehyde sugar (an aldohexose), so why doesn't it respond?

The answer lies in structure, not classification. In aqueous solution, glucose does not exist as the open-chain aldehyde form. Instead, it undergoes intramolecular cyclization: the hydroxyl group on C-5 attacks the carbonyl carbon (C-1), forming a six-membered ring called a pyranose (or occasionally a five-membered furanose). This cyclic form is a hemiacetal, not an aldehyde.

Open-chain aldehyde⇌Cyclic hemiacetal (pyranose)\text{Open-chain aldehyde} \rightleftharpoons \text{Cyclic hemiacetal (pyranose)}

At equilibrium in water, more than 99% of glucose molecules are in the cyclic form. The tiny fraction of open-chain aldehyde present at any moment is insufficient to give a positive 2,4-DNP test under normal conditions. The reagent requires a free carbonyl group to attack, and the hemiacetal oxygen occupies that reactive site.

Note

Glucose does give tests like Fehling's or Tollens' because those involve oxidation under basic conditions, which shifts the equilibrium and opens the ring. The 2,4-DNP test, being a simple condensation reaction, does not have that driving force.


(b) Why the two DNA strands are complementary, not identical

DNA's double helix consists of two polynucleotide strands running antiparallel (one 5'→3', the other 3'→5'). If the strands were identical, they would have the same sequence of bases read in the same direction—but that would violate the structural rules of base pairing.

The key concept is complementary base pairing through hydrogen bonds:

Base on Strand 1Base on Strand 2H-bonds
Adenine (A)Thymine (T)2
Guanine (G)Cytosine (C)3

These pairs are dictated by:

  1. Geometry: A purine (A or G, two-ring) must pair with a pyrimidine (T or C, one-ring) to maintain constant width across the helix (about 2 nm).
  2. Hydrogen bonding: A and T form two H-bonds; G and C form three. No other pairing (A–C, G–T) provides the correct number or geometry of hydrogen bonds.

If one strand reads 5'-ATGC-3', the complementary strand must read 3'-TACG-5' (or equivalently 5'-GCAT-3' when flipped). The sequences are not the same—they are determined by each other. This complementarity is the basis of DNA replication: each strand serves as a template for synthesizing its partner.

Important

Complementarity ensures genetic fidelity. During replication, each original strand directs the assembly of a new complementary strand, preserving the information across generations.


(c) Why starch and cellulose differ despite both being glucose polymers

Both starch and cellulose are polysaccharides made exclusively of D-glucose monomers, yet their properties could not be more different: starch is digestible by humans and forms granules; cellulose is indigestible and forms tough plant fibers. The difference is entirely due to the type of glycosidic linkage.

Starch: α-glycosidic linkages

Starch consists of two components:

  • Amylose: unbranched chains of glucose linked by α(1→4) glycosidic bonds.
  • Amylopectin: branched chains with α(1→4) bonds in the linear segments and α(1→6) bonds at branch points. …

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