Q.How do you explain the presence of an aldehydic group in a glucose molecule?
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🔒 Start your 14-day free trial to unlock the full solution →Concept understanding — Glucose Cyclization
Glucose Cyclization: From a Straight Chain to a Ring
Imagine you have a long, flexible chain with a hook at one end and an eyelet at the other. If you swing that chain around, the hook can snap into the eyelet, forming a loop. That's the core idea behind glucose cyclization.
Glucose in its simplest written form is a straight chain of six carbon atoms with an aldehyde group (−CHO) at one end. But in water (like in your blood), this chain doesn't stay straight. The aldehyde group reacts with the alcohol group on the fifth carbon, forming a stable six-membered ring.
Why does this happen?
The aldehyde carbon is electrophilic (electron-poor), and the oxygen on carbon-5 has lone pairs (nucleophilic). They attack each other, forming a new bond. This creates a hemiacetal — a carbon bonded to both an −OH and an −OR group. The ring is more stable than the open chain in solution.
The open-chain form of glucose exists in equilibrium with the cyclic form, but at any given time, over 99% of glucose molecules are in the cyclic form.
The precise statement
Glucose cyclization is an intramolecular nucleophilic addition where the aldehyde group at C1 reacts with the hydroxyl group at C5, forming a six-membered pyranose ring (named after pyran, a six-membered oxygen heterocycle). This reaction creates a new chiral center at C1, giving two possible stereoisomers called anomers: α and β.
The two anomers
When the ring forms, the oxygen from C5 becomes part of the ring. The carbon that was the aldehyde (now C1) becomes a new chiral center. The −OH group at this new center can point:
- Down (relative to the ring plane) → α-D-glucose
- Up → β-D-glucose
The α and β anomers are diastereomers, not enantiomers. They differ only at the anomeric carbon (C1). In solution, they interconvert through the open-chain form — a process called mutarotation.
How to draw it (Haworth projection)
- Draw a hexagon with an oxygen atom at the top-right corner.
- Number the carbons clockwise from the oxygen: C1 is the carbon to the right of oxygen, C2 next, and so on.
- For α-D-glucose, the −OH at C1 points down (opposite to the CH2OH group at C5).
- For β-D-glucose, the −OH at C1 points up (same side as the CH2OH group). …
Why this formula?
Glucose Cyclization: Why the Ring Forms
Glucose cyclization is a classic example of an intramolecular reaction — a molecule reacting with itself. Let's build the understanding step by step.
1. The Starting Point: Open-Chain Glucose
Glucose (C6H12O6) in its open-chain form has:
- An aldehyde group (−CHO) at carbon 1 (C1)
- A hydroxyl group (−OH) at carbon 5 (C5)
The aldehyde is electrophilic (electron-deficient at the carbonyl carbon), and the hydroxyl is nucleophilic (electron-rich oxygen with lone pairs).
2. Why Cyclization Happens: Thermodynamic & Kinetic Favorability
The Key Insight
The molecule is flexible — it can bend so that the C5 hydroxyl oxygen approaches the C1 aldehyde carbon. This brings two reactive groups into close proximity.
- Entropy is favorable: One molecule becomes one ring — no loss of translational entropy (unlike two separate molecules reacting).
- Ring strain is manageable: A 5- or 6-membered ring (furanose or pyranose) has minimal angle strain (close to tetrahedral angles).
Result: The reaction is reversible but strongly favors the cyclic form — in aqueous solution, >99% of glucose exists as the ring.
3. The Reaction: Hemiacetal Formation
The nucleophilic oxygen of the C5 hydroxyl attacks the electrophilic carbonyl carbon of C1:
R-CHO+R’-OH⇌R-CH(OH)(OR’)
This is a hemiacetal — a carbon bonded to both an −OH and an −OR group.
Mechanism (simplified)
- Protonation of the carbonyl oxygen (acid-catalyzed) makes C1 more electrophilic.
- Nucleophilic attack by the C5 oxygen.
- Deprotonation yields the cyclic hemiacetal.
4. The Key Formula(e): Ring Size & Anomeric Carbon
Ring Size Determination
The ring size depends on which hydroxyl attacks:
- C5 hydroxyl → pyranose (6-membered ring: 5 carbons + 1 oxygen)
- C4 hydroxyl → furanose (5-membered ring: 4 carbons + 1 oxygen)
For D-glucose, the C5 attack is overwhelmingly favored, giving the pyranose form.
The Anomeric Carbon
The new chiral center formed at C1 is called the anomeric carbon. Two stereoisomers arise:
- α-anomer: −OH at C1 is trans to the −CH2OH group (axial in the chair conformation)
- β-anomer: −OH at C1 is cis to the −CH2OH group (equatorial in the chair conformation)
Why two forms? The attack can occur from either face of the planar carbonyl group — leading to two possible configurations at the new stereocenter.
5. The Equilibrium Constant & Mutarotation
The interconversion between α and β anomers is called mutarotation:
α-D-glucopyranose⇌open chain⇌β-D-glucopyranose
At equilibrium (in water at 20°C):
- β-D-glucopyranose: ~64%
- α-D-glucopyranose: ~36%
- Open chain: <0.1% …
The key idea is that glucose exists in a dynamic equilibrium between its open-chain (aldehydic) form and its cyclic (hemiacetal) form. Although the cyclic form dominates in solution, the open-chain form is continuously regenerated.
Reasoning:
- Glucose contains an aldehyde group (−CHO) at carbon 1 in its open-chain structure.
- In solution, the aldehyde group reacts with the hydroxyl group on carbon 5 to form a stable six-membered hemiacetal ring (pyranose form).
- This ring-opening and ring-closing is reversible — the equilibrium constantly produces a tiny amount of the free aldehyde form. …
Glucose exists predominantly in a cyclic hemiacetal form, but a tiny fraction of the molecules are in the open-chain aldehyde form at equilibrium. This open-chain form is responsible for the characteristic reactions of an aldehydic group (e.g., with Tollens’ reagent, Fehling’s solution, or HCN), even though the cyclic form lacks a free –CHO group.
The puzzle is this: glucose gives all the classic tests for an aldehyde — it reduces Tollens’ reagent to a silver mirror, turns Fehling’s solution brick-red, and adds HCN — yet its IR spectrum shows no strong C=O stretch near 1720–1740 cm⁻¹, and its crystalline form is a cyclic hemiacetal with no free –CHO. How can both be true?
The answer lies in dynamic equilibrium between the open-chain aldehyde and the cyclic hemiacetal forms. Let’s walk through it.
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Glucose cyclizes spontaneously.
The –OH on carbon 5 attacks the aldehyde carbon (C1), forming a six-membered pyranose ring. This creates a new chiral centre at C1 (the anomeric carbon), giving α and β anomers. In this cyclic form, the –CHO group is gone — it’s now a hemiacetal –OH.
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The equilibrium heavily favours the ring.
In aqueous solution, more than 99% of glucose molecules are in the cyclic form. The open-chain aldehyde is present only in trace amounts — about 0.02% at room temperature. That’s why spectroscopic methods (which “see” the average structure) show no aldehyde signal.
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But the open-chain form is constantly regenerated.
The ring opens and closes rapidly — thousands of times per second. Even though the open-chain concentration is tiny, it is continuously replenished. Any reagent that reacts with the –CHO group (like Tollens’ reagent) will trap the open-chain form as it appears, pulling the equilibrium to the right. This is Le Chatelier’s principle in action: the reagent consumes the aldehyde, so more ring opens to replace it.
TipThink of it like a tiny leak in a dam — the leak is small, but water keeps flowing through it because the reservoir is huge. Here, the “reservoir” is the cyclic form, and the “leak” is the open-chain aldehyde.
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The same principle explains mutarotation. …
Method: Open-Chain vs. Cyclic Equilibrium Explanation
This method explains the apparent contradiction — glucose has an aldehyde group, yet it exists mostly as a cyclic hemiacetal.
Step 1: Recall the open-chain (Fischer) structure of glucose
- Glucose is an aldohexose: a six-carbon chain with an aldehyde group at C1.
- In its open-chain form, the aldehyde group (−CHO) is free and can undergo typical aldehyde reactions (e.g., with Fehling’s solution, Tollen’s reagent).
Step 2: Introduce the cyclization equilibrium
- In solution, glucose exists predominantly as a cyclic hemiacetal (pyranose ring).
- The aldehyde group at C1 reacts with the hydroxyl group at C5 to form an intramolecular hemiacetal.
- This creates a new chiral centre at C1 (the anomeric carbon), giving α and β anomers.
Step 3: Explain why the aldehyde group is still “detectable”
- The open-chain and cyclic forms are in dynamic equilibrium.
- Although only ~0.02% of glucose molecules are in the open-chain form at any instant, the equilibrium constantly shifts to replenish the open-chain form as it reacts.
- Therefore, when a reagent that reacts with aldehydes (e.g., Fehling’s solution, bromine water) is added, the open-chain form is consumed, and the equilibrium shifts to produce more open-chain molecules.
Step 4: State the key conclusion …
Common Mistakes in Explaining the Aldehydic Group in Glucose
Mistake 1: Forgetting That Glucose Exists Mostly in Cyclic Form
The error: Students state "glucose has an aldehydic group" as if the open-chain form is the dominant structure in solution.
Why it's wrong: In aqueous solution, less than 1% of glucose molecules exist in the open-chain (aldehydic) form. The vast majority (>99%) exists as a cyclic hemiacetal (pyranose or furanose ring).
How to avoid: Always clarify that the aldehydic group is present in the open-chain form, which is in dynamic equilibrium with the cyclic forms. The cyclic form has no free aldehydic group — it has a hemiacetal group instead.
Mistake 2: Confusing the Aldehydic Group with the Hemiacetal Group
The error: Students point to the anomeric carbon (C1) in the cyclic structure and call it an aldehydic carbon.
Why it's wrong: In the cyclic form, C1 is a hemiacetal carbon (bonded to two oxygens — one from the ring oxygen and one from the -OH group). It is not an aldehydic carbon (which would have a C=O double bond).
How to avoid: Draw both forms side by side:
- Open chain: C1 has C=O (aldehydic)
- Cyclic: C1 has C−OH and C−O−C (hemiacetal)
Mistake 3: Ignoring the Evidence for the Aldehydic Group
The error: Students simply state "glucose has an aldehydic group" without citing experimental evidence.
Why it's wrong: The question asks how do you explain — this requires reasoning from experimental observations.
How to avoid: Memorize and explain at least two key tests:
| Test | Observation | What it proves |
|---|---|---|
| Tollens' test | Silver mirror forms | Reducing sugar → aldehydic group present |
| Fehling's test | Red precipitate of Cu2O | Reducing sugar → aldehydic group present |
| Schiff's test | Pink/magenta colour | Aldehydic group present |
Key insight: These tests work because the small amount of open-chain form present in equilibrium reacts, and the equilibrium shifts to replenish it (Le Chatelier's principle).
Mistake 4: Not Mentioning the Equilibrium
The error: Students treat the open-chain and cyclic forms as separate molecules.
Why it's wrong: They are in dynamic equilibrium:
Open-chain (aldehydic)⇌Cyclic (hemiacetal) …
- KCET 2024Set B-21 markMCQQ.α–D–(+)–glucose and β–D–(+)–glucose are: (A) Enantiomers (B) Conformers (C) Epimers (D) Anomers
›Reveal solutionSolution
α- and β-D-glucose differ in configuration at exactly one carbon — C-1, the anomeric carbon created on ring closure — so by definition they are anomers.
1. Where the α/β difference comes from
Open-chain D-glucose is an aldohexose. Its C-5 –OH attacks the C-1 aldehyde carbon intramolecularly, forming a six-membered cyclic hemiacetal (the pyranose ring):
CHO (C-1, planar, sp2)⟶HCOH(C-1, sp3, a NEW stereocentre)
Because the carbonyl carbon is planar, the ring oxygen can close from either face, so the new –OH at C-1 ends up either:
- down (trans to the CH2OH; on the same side as the C-2 OH in Fischer projection) ⇒ α-D-(+)-glucose, or
- up ⇒ β-D-(+)-glucose.
The carbon whose configuration is fixed by this ring closure is called the anomeric carbon, and the two products are anomers. In solution they interconvert through the open-chain form — the phenomenon of mutarotation ([α]D drifting from +111∘ for pure α and +19∘ for pure β to the equilibrium +52.7∘).
2. Eliminate the other terms precisely
- (A) Enantiomers — non-superimposable mirror images: they must differ at every stereocentre. α- and β-D-glucose share the same configuration at C-2, C-3, C-4 and C-5, so they are not mirror images (they are diastereomers). ✗ …
- COMEDK 2024Set 2024-A1 markMCQQ.Which of the following statement is not true about glucose? (A) Glucose does not give Schiff's reagent test (B) Glucose on reaction with HI and red P at 373 K gives a mixture of cyclohexane and 1-iodohexane (C) Both α-D-glucose and β-D-glucose undergo mutarotation in aqueous solutions (D) Glucose reacts with hydroxylamine to form an oxime
›Reveal solutionSolution
The question asks which statement about glucose is false. By checking each option against known glucose chemistry, we find that option (B) is incorrect because the reaction with HI and red P at 373 K yields n-hexane, not a mixture of cyclohexane and 1-iodohexane.
Concept & Intuition
Glucose is an aldohexose — a six-carbon sugar with an aldehyde group (in open-chain form) and multiple hydroxyl groups. Its reactions depend on these functional groups: the aldehyde gives typical carbonyl reactions (oxime formation, no Schiff’s test because it’s usually cyclic), the hydroxyls can be reduced, and the anomeric carbon allows mutarotation. To spot the false statement, we need to recall the specific outcome of each reaction, especially the drastic reduction with HI and red phosphorus, which removes all oxygen atoms.
Step-by-step reasoning
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Option (A): Glucose does not give Schiff’s reagent test
Schiff’s reagent tests for aldehydes, but glucose exists predominantly in cyclic hemiacetal form, where the aldehyde group is masked. The equilibrium concentration of free aldehyde is too low to give a positive test under normal conditions. Thus, this statement is true.
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Option (B): Glucose on reaction with HI and red P at 373 K gives a mixture of cyclohexane and 1-iodohexane
HI and red phosphorus are a powerful reducing agent that removes all hydroxyl groups (as water) and reduces any carbonyl to methylene. For glucose (C₆H₁₂O₆), the complete reduction yields straight-chain n-hexane (C₆H₁₄). No cyclohexane forms because the carbon skeleton remains unbranched and no ring closure occurs under these conditions. Also, 1-iodohexane would be an intermediate, but excess HI and red P drive reduction all the way to the alkane. So the product is n-hexane, not a mixture of cyclohexane and 1-iodohexane. This statement is false.
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Option (C): Both α-D-glucose and β-D-glucose undergo mutarotation in aqueous solutions …
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- COMEDK 2024Set 2024-E1 markMCQQ.Given are 4 statements related to the chemical properties of Glucose. Identify the two incorrect statements from the following. A. It reacts with Br2 (aq) to form Saccharic acid. B. Reacts with Acetic anhydride to form Glucose tetraacetate. C. Reacts with Hydroxylamine to give Glucose oxime. D. It reacts with ammoniacal AgNO3 to form ammonium salt of Gluconic acid with deposition of silver. (A) A & B (B) C & D (C) B & D (D) A & C
›Reveal solutionSolution
Statements A (Br2 water → saccharic acid) and B (acetic anhydride → tetraacetate) are the incorrect ones; C and D correctly describe glucose chemistry.
A. Br2(aq) → Saccharic acid — INCORRECT. Bromine water is a mild oxidising agent; it oxidises only the –CHO group of glucose to –COOH, giving gluconic acid. Saccharic (glucaric) acid, a dicarboxylic acid, requires the stronger oxidant conc. HNO3.
B. Acetic anhydride → Glucose tetraacetate — INCORRECT. Glucose has five –OH groups, all acetylated, giving glucose pentaacetate, not tetraacetate. …
- COMEDK 2024Set 2024-M1 markMCQQ.Identify the 2 chemical tests which is not answered by Glucose having an open chain structure [A] Reaction with Schiff's reagent and with Sodium bisulphite [B] Reaction with HCN and with HI [C] Reaction with HNO3 and with Acetic anhydride [D] Reaction with aqueous Bromine and with Hydroxylamine (A) [D] (B) [B] (C) [C] (D) [A]
›Reveal solutionSolution
Glucose’s open-chain aldehyde structure explains most of its reactions, but two tests—reaction with Schiff’s reagent and with sodium bisulphite—are not given by the open-chain form because in solution glucose exists predominantly as a cyclic hemiacetal, which lacks a free aldehyde group.
The key concept here is mutarotation and the equilibrium between open-chain and cyclic forms of glucose. In water, glucose is almost entirely (over 99%) in its cyclic pyranose form. Only a tiny fraction exists as the free aldehyde. Many aldehyde-specific tests require a high enough concentration of the free aldehyde to give a visible positive result. Some tests are so sensitive that even the trace amount of open-chain form suffices; others are not.
Let’s examine each pair of tests.
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Reaction with Schiff’s reagent and with Sodium bisulphite
- Schiff’s reagent (fuchsine decolorized by SO₂) gives a magenta color with aldehydes. However, glucose gives a very slow or no color change because the equilibrium concentration of the free aldehyde is too low to react quickly.
- Sodium bisulphite (NaHSO₃) adds to aldehydes to form a crystalline bisulphite addition product. Glucose does not form such a solid adduct under normal conditions, again because the open-chain form is too scarce.
- Conclusion: These two tests are not answered by the open-chain structure in practice.
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Reaction with HCN and with HI
- HCN adds to the carbonyl group of the open-chain form to give a cyanohydrin. This reaction does occur (though slowly) because the equilibrium shifts as the open-chain form is consumed.
- HI reduces the aldehyde group (and also the alcohol groups) under drastic conditions, but the aldehyde is still the reactive site.
- Conclusion: Both are possible via the open-chain form.
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Reaction with HNO₃ and with Acetic anhydride
- HNO₃ oxidizes the aldehyde group to a carboxylic acid (giving gluconic acid) and also the terminal CH₂OH to COOH (giving glucaric acid). This clearly involves the open-chain aldehyde.
- Acetic anhydride reacts with all –OH groups (including the hemiacetal OH) to form an acetate. This does not require the open-chain form; it reacts with the cyclic form as well. So this test is not exclusive to the open-chain structure, but the question asks which tests are not answered by the open-chain structure — meaning which tests fail if only the open-chain form is considered. Acetic anhydride works fine, so it’s not a “not answered” case.
- Conclusion: HNO₃ works via the open-chain; acetic anhydride works anyway.
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Reaction with aqueous Bromine and with Hydroxylamine …
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- COMEDK 2023Set 2023-E1 markMCQQ.Structures of 3 Monosaccharides are given below. Two of them are Anomers. Identify the two Anomers. (A) II is the anomer of both I and II (B) I and II are Anomers. (C) II and III are Anomers. (D) I and III are Anomers
›Reveal solutionSolution
[I] and [III] differ only at the anomeric carbon C1 (identical at C2–C4), so they are anomers; [II] also differs at C2 and is not an anomer of either.
Definition: anomers are a special pair of epimers (cyclic monosaccharides) that differ in configuration only at the anomeric carbon (C1, the former carbonyl carbon).
Compare the structures at C1–C4 (left/right substituents):
- [I]: C1 = H/OH, C2 = H/OH, C3 = HO/H, C4 = H/OH
- [III]: C1 = HO/H, C2 = H/OH, C3 = HO/H, C4 = H/OH
- [II]: C1 = HO/H, C2 = HO/H, C3 = HO/H, C4 = H/OH …
- COMEDK 2023Set 2023-M1 markMCQQ.Pick out the incorrect statement(s) from the following. 1. Glucose exists in two different crystalline forms, α-D-glucose and β-D-glucose. 2. α-D-glucose and β-D-glucose are anomers. 3. α-D-glucose and β-D-glucose are enantiomers. 4. Cellulose is a straight chain polysaccharide made of only β-D-glucose units. 5. Starch is a mixture of amylase and amylopectin, both contain unbranched chain of α-D-glucose units. (A) 1 and 2 only (B) 2 and 3 only (C) 3 and 4 only (D) 3 and 5 only
›Reveal solutionSolution
Statements 3 (anomers, not enantiomers) and 5 (amylopectin is branched) are the incorrect ones.
Evaluating each statement:
- Glucose exists as two crystalline forms α- and β-D-glucose — correct.
- α- and β-D-glucose are anomers (differ only in configuration at the anomeric C-1) — correct.
- α- and β-D-glucose are enantiomers — incorrect; they are anomers/diastereomers, not mirror images.
- Cellulose is a straight (unbranched) chain of only β-D-glucose units — correct. …
- KCET 2020Set A-11 markMCQQ.C1−C4 glycosidic bond is NOT found in (A) starch (B) maltose (C) sucrose (D) lactose
›Reveal solutionSolution
A C1−C4 glycosidic bond links carbon-1 of one sugar to carbon-4 of another. Sucrose has a C1−C2 bond instead, so it is the one that does not contain a C1−C4 linkage. The correct option is (C).
The key to this question is understanding what a glycosidic bond is and how the numbering of carbon atoms works in sugars. A glycosidic bond is a covalent bond that joins a carbohydrate molecule to another group, which could be another carbohydrate. The notation C1−C4 tells us exactly which carbon atoms are involved: the anomeric carbon (C1) of one monosaccharide is linked to the C4 carbon of another.
Let's check each option.
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Starch is a polymer of glucose. The main linkage in starch (both amylose and amylopectin) is an α-1,4-glycosidic bond — that is, a C1−C4 bond. So starch definitely contains this bond.
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Maltose is a disaccharide made of two glucose units. They are joined by an α-1,4-glycosidic bond. Again, this is a C1−C4 linkage.
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Sucrose is a disaccharide of glucose and fructose. The glycosidic bond here is between the C1 of glucose and the C2 of fructose. This is a C1−C2 bond, not C1−C4. This is the odd one out.
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Lactose is a disaccharide of galactose and glucose. The bond is a β-1,4-glycosidic bond — the C1 of galactose links to the C4 of glucose. So it does have a C1−C4 linkage. …
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- KCET 2020Set A-11 markMCQQ.Which of the following monomers can undergo condensation polymerization ? (A) Propene (B) Styrene (C) Glycine (D) Isoprene
›Reveal solutionSolution
Condensation polymerisation requires a bifunctional monomer; only glycine carries two functional groups (−NH2 and −COOH) and can polymerise with loss of water.
Step 1 — The two modes of polymerisation (the concept).
- Addition polymerisation: monomers must contain a multiple bond (usually C=C). The π bond opens and the units simply add on; nothing is eliminated, so the polymer's empirical formula equals the monomer's. (Polythene, PVC, polystyrene, rubber.)
- Condensation polymerisation: monomers must be bi- or poly-functional — carrying two reactive groups such as −OH, −COOH, −NH2. Repeated condensation between these groups builds the chain and eliminates a small molecule (usually H2O, sometimes HCl or CH3OH). (Nylon-6,6, Terylene, Bakelite.)
So the question is really: which monomer has two functional groups rather than a double bond?
Step 2 — Examine each option.
- (A) Propene, CH3−CH=CH2 — a single C=C, no functional groups → addition polymerisation → polypropylene.
- (B) Styrene, C6H5−CH=CH2 — vinyl double bond → addition → polystyrene.
- (C) Glycine, H2N−CH2−COOH — an α-amino acid carrying two different functional groups: an amino group −NH2 and a carboxyl group −COOH. ✓ …
- KCET 2018Set A-11 markMCQQ.The two forms of D-Glucopyranose are called (A) Diastereomers (B) Anomers (C) Epimers (D) Enantiomers
›Reveal solutionSolution
The two forms of D-glucopyranose differ only at the anomeric carbon (C1) when the ring closes, making them anomers — the correct answer is (B).
The concept: why the ring creates a special pair
D-Glucose exists predominantly as a six-membered pyranose ring. When the open-chain aldehyde form cyclises, the carbonyl carbon (C1) becomes a new chiral centre — the anomeric carbon. The two possible configurations at this carbon (OH pointing down or up in the standard Haworth projection) give rise to α and β forms. These are not mirror images, nor do they differ at any other single carbon; they are a specific subclass of diastereomers called anomers.
Watch outA common mistake is to confuse anomers with epimers. Epimers differ at any one chiral carbon except the anomeric carbon. Anomers differ only at the anomeric carbon — that is the defining feature.
Step-by-step reasoning
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Identify the two forms.
D-Glucopyranose exists as α-D-glucopyranose and β-D-glucopyranose. In the α form, the OH at C1 is trans to the CH2OH group (axial in the chair conformation); in the β form, it is cis (equatorial).
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Check the relationship.
- Are they mirror images? No — they are not enantiomers (option D).
- Do they differ at a single chiral carbon other than C1? No — they differ only at C1, so they are not epimers (option C). …
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- KCET 2018Set A-11 markMCQQ.The glycosidic linkage involved in linking the glucose units in amylose part of starch is (A) C1−C4 β-linkage (B) C1−C6 α-linkage (C) C1−C6 β-linkage (D) C1−C4 α-linkage
›Reveal solutionSolution
Amylose is a linear polymer of glucose linked by C1−C4 α-glycosidic bonds. The correct option is (D).
The question is about the specific type of glycosidic bond that joins glucose units in amylose, which is the linear component of starch. Starch is a mixture of two polysaccharides: amylose (unbranched) and amylopectin (branched). The key is to recall the stereochemistry and position of the linkage.
Glucose can exist in two anomeric forms: α and β, depending on the orientation of the -OH group at carbon 1. In starch, the glucose units are all in the α-D-glucopyranose form. The linkage between them always involves carbon 1 of one glucose and a specific carbon of the next glucose.
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Identify the structure of amylose. Amylose is a long, unbranched chain of glucose molecules. Each glucose is connected to the next by a bond that forms between the anomeric carbon (C1) of one unit and the hydroxyl group on carbon 4 of the next unit. This is a C1−C4 linkage.
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Determine the stereochemistry of the bond. Because the glucose units in starch are α-D-glucose, the glycosidic bond is formed with the α configuration at C1. This means the oxygen bridge is oriented downward (in the standard Haworth projection) from C1. This is called an α-linkage. …
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