Carbohydrates: classification and preparation of glucose
Rice, bread, sugar and paper are all carbohydrates.
Carbohydrates are polyhydroxy aldehydes/ketones or compounds yielding them on hydrolysis: mono-, oligo-, polysaccharides.
In the figure : Classification.
Rule 1: Mono/oligo/poly — Monosaccharides do not hydrolyse; disaccharides have two units; polysaccharides many.
- Easy : Glucose = mono.
- Medium : Sucrose = di.
- Exam-type : Starch = poly.
Rule 2: Aldose/ketose — –CHO ⇒ aldose; >C=O ⇒ ketose; triose … hexose by carbon count.
- Easy : Glucose = aldohexose.
- Medium : Fructose = ketohexose.
- Exam-type : Ribose = aldopentose.
Rule 3: Making glucose — Sucrose + H₂O (dil. HCl/H₂SO₄) ⇒ glucose + fructose. Starch + H₂O (H⁺, 393 K, pressure) ⇒ glucose.
- Easy : 34.2 g sucrose ⇒ 18.0 g glucose + 18.0 g fructose.
- Medium : Mass 34.2 + 1.8 = 36.0 g.
- Exam-type : Industrial: from starch.
Calculation: glucose from 34.2 g sucrose
- Step 1: n = 34.2 ÷ 342.3 = 0.1 mol.
- Step 2: 1 mol sucrose ⇒ 1 mol glucose + 1 mol fructose.
- Step 3: 0.1 × 180.16 = 18.0 g of each.
CET level (MCQ)
- CET 1) Glucose is a(n)? 1) aldohexose 2) ketohexose 3) aldopentose 4) disaccharide — Answer: 1).
- CET 2) Hydrolysis of sucrose gives? 1) glucose + fructose 2) 2 glucose 3) glucose + galactose 4) 2 fructose — Answer: 1).
Real-life use: Food, energy, fuel (ethanol).
Monosaccharides do not hydrolyse; glucose = aldohexose; fructose = ketohexose.
Calling fructose an aldose.
Aldose = –CHO; ketose = C=O.
Memory clue: "Glucose has the aldehyde; fructose has the ketone".
Spot the difference
| Sugar | Group | Class |
|---|---|---|
| Glucose | –CHO | aldohexose |
| Fructose | >C=O | ketohexose |
| Sucrose | — | disaccharide |
Practice questions
- 1What are carbohydrates?
- 2Mono vs oligo vs poly.
- 3Aldose vs ketose.
- 4How is glucose prepared?
- 534.2 g sucrose ⇒ ?
- 6Type of ribose?
- 7Starch hydrolysis conditions.
- 8What is a hexose?
Show answers (try them yourself first)
- 1Polyhydroxy carbonyl compounds.
- 2Number of hydrolysis products.
- 3–CHO vs C=O.
- 4Sucrose/starch + H⁺.
- 518.0 g glucose + 18.0 g fructose.
- 6Aldopentose.
- 7H⁺, 393 K, pressure.
- 8A six-carbon sugar.
Structure and stereochemistry of glucose
Doctors test for glucose with Benedict/Fehling because it carries –CHO.
Glucose = HOCH₂–(CHOH)₄–CHO. Four chiral carbons ⇒ 2⁴ = 16 stereoisomers; natural glucose is D(+).
In the figure : Structural evidence.
Rule 1: Open-chain evidence — HI ⇒ n-hexane (straight 6 C). Br₂ water ⇒ gluconic acid (–CHO). HNO₃ ⇒ saccharic acid (terminal 1° OH).
- Easy : Pentaacetate ⇒ five OH.
- Medium : 18.0 g glucose ⇒ 39.0 g pentaacetate.
- Exam-type : NH₂OH ⇒ oxime ⇒ C=O.
Rule 2: D and L — OH on the chiral carbon farthest from CHO (C-5) on the right ⇒ D; on the left ⇒ L.
- Easy : The mirror image of D is L.
- Medium : D(+) rotates plane light to the right.
- Exam-type : D/L ≠ d/l.
Rule 3: Limitations — Glucose fails the NaHSO₃ and Schiff tests and its pentaacetate does not react with NH₂OH, so a ring form is needed.
- Easy : Schiff ⇒ no.
- Medium : Mutarotation.
- Exam-type : Two anomers.
Reasoning: stereoisomers of an aldohexose
- Step 1: Chiral carbons = 4 (C2–C5).
- Step 2: 2⁴ = 16.
- Step 3: 8 D + 8 L.
CET level (MCQ)
- CET 1) Chiral carbons in glucose? 1) 4 2) 3 3) 5 4) 6 — Answer: 1).
- CET 2) Bromine water with glucose ⇒ ? 1) gluconic acid 2) saccharic acid 3) n-hexane 4) sorbitol — Answer: 1).
Real-life use: Diabetes tests, IV fluids.
HI ⇒ hexane; Br₂ water ⇒ gluconic; HNO₃ ⇒ saccharic; 4 C* ⇒ 16.
Mistaking D/L for d/l (rotation).
D/L = configuration; (+)/(–) = rotation direction.
Memory clue: "C-5 OH on the right = D".
Spot the difference
| Reagent | Product |
|---|---|
| HI | n-hexane |
| Br₂/H₂O | gluconic acid |
| HNO₃ | saccharic acid |
Practice questions
- 1How is the open chain proved?
- 2How 2⁴ = 16?
- 3D vs L.
- 4What does pentaacetate show?
- 5Why no Schiff test?
- 6Product with HNO₃.
- 7C* in a ketohexose?
- 8Pentaacetate from 18.0 g?
Show answers (try them yourself first)
- 1HI ⇒ hexane, Br₂ ⇒ acid.
- 24 chiral carbons.
- 3C-5 OH right/left.
- 4Five OH groups.
- 5A ring (hemiacetal) form.
- 6Saccharic acid.
- 73 ⇒ 8 isomers.
- 839.0 g.
Ring structures, anomers and fructose
A fresh glucose solution slowly changes its optical rotation — mutarotation.
C-1 aldehyde reacts with the C-5 OH forming a hemiacetal ⇒ six-membered pyranose ring. C-1 OH down ⇒ α, up ⇒ β (anomers).
In the figure : Haworth structures.
Rule 1: Anomers — α-D-glucose [α]D = +112°; β-D-glucose +18.7°; they differ only at C-1 (the anomeric carbon).
- Easy : α: OH down.
- Medium : β: OH up.
- Exam-type : Both are diastereomers.
Rule 2: Mutarotation — In solution α ⇌ β via the open chain; rotation settles at +52.7° ⇒ ≈ 36 % α : 64 % β.
- Easy : 112x + 18.7(1–x) = 52.7.
- Medium : x ≈ 0.364.
- Exam-type : β is more stable.
Rule 3: Fructose — A ketohexose; ring is five-membered furanose (O between C-2 and C-5). D-fructose [α]D = –92.4°, hence 'laevulose'.
- Easy : The sweetest sugar.
- Medium : Fructose gives Fehling's test.
- Exam-type : Sweetest of the hexoses.
Calculation: α fraction at equilibrium
- Step 1: 112x + 18.7(1 – x) = 52.7.
- Step 2: 93.3x = 34.0 ⇒ x ≈ 0.364.
- Step 3: α ≈ 36 %, β ≈ 64 %.
CET level (MCQ)
- CET 1) Anomers differ at which carbon? 1) C-1 2) C-2 3) C-5 4) C-6 — Answer: 1).
- CET 2) Members in the glucose pyranose ring? 1) 6 2) 5 3) 4 4) 7 — Answer: 1).
Real-life use: Honey, sweeteners, energy drinks.
α = OH down; β = up; equilibrium +52.7°; fructose five-membered.
Confusing α/β with D/L.
α/β concern the C-1 OH; D/L concerns C-5.
Memory clue: "α = down (alpha-low)".
Spot the difference
| Form | [α]D |
|---|---|
| α-D-glucose | +112° |
| β-D-glucose | +18.7° |
| Equilibrium | +52.7° |
Practice questions
- 1What are anomers?
- 2What is mutarotation?
- 3Find the α fraction.
- 4Ring of fructose.
- 5Pyranose vs furanose.
- 6Why is fructose laevulose?
- 7What is a hemiacetal?
- 8Difference between α and β.
Show answers (try them yourself first)
- 1Isomers differing at C-1.
- 2Rotation changes through α ⇌ β.
- 336 %.
- 4Five-membered.
- 56 vs 5.
- 6[α]D –92.4°.
- 7C(OH)(OR).
- 8C-1 OH down/up.
Disaccharides and polysaccharides
The starch in flour, the sugar in honey and the lactose in milk are all here.
A glycosidic bond is the C–O–C link joining two sugars: sucrose (1→2), maltose and lactose (1→4).
In the figure : Di- and polysaccharides.
Rule 1: Disaccharides — Sucrose = α-glucose + β-fructose (1→2), non-reducing. Maltose = glucose + glucose (α-1,4), reducing. Lactose = galactose + glucose (β-1,4), reducing.
- Easy : Sucrose with Fehling ⇒ none.
- Medium : Maltose ⇒ red Cu₂O.
- Exam-type : Lactose = milk sugar.
Rule 2: Invert sugar — Sucrose [α]D = +66.5°; after hydrolysis the glucose + fructose mixture is ≈ –20°, so rotation inverts.
- Easy : Fructose (–92.4°) dominates.
- Medium : Hence 'invert'.
- Exam-type : Honey contains invert sugar.
Rule 3: Polysaccharides — Starch: amylose (α-1,4 linear, 15–20 %) + amylopectin (α-1,4 and α-1,6 branched, 80–85 %). Cellulose: β-1,4. Glycogen: highly branched.
- Easy : Starch + I₂ ⇒ blue.
- Medium : Humans cannot digest cellulose.
- Exam-type : Glycogen = animal starch.
Reasoning: why no Fehling result for sucrose?
- Step 1: Glucose C-1 and fructose C-2 are joined together.
- Step 2: No free hemiacetal OH remains.
- Step 3: So it is non-reducing.
CET level (MCQ)
- CET 1) Non-reducing disaccharide? 1) sucrose 2) maltose 3) lactose 4) cellobiose — Answer: 1).
- CET 2) Starch + iodine ⇒ ? 1) blue 2) red 3) yellow 4) green — Answer: 1).
Real-life use: Food, cloth (cotton), paper.
Sucrose non-reducing; cellulose β; starch α; I₂ ⇒ blue.
Calling sucrose reducing.
Starch is α-1,4, cellulose β-1,4 — only the link direction differs.
Memory clue: "sucrose = safe (non-reducing)".
Spot the difference
| Sugar | Units | Bond |
|---|---|---|
| Sucrose | Glu + Fru | α-1,2-β |
| Maltose | Glu + Glu | α-1,4 |
| Lactose | Gal + Glu | β-1,4 |
Practice questions
- 1Structure of sucrose.
- 2What is invert sugar?
- 3Amylose vs amylopectin.
- 4Why isn't cellulose digested?
- 5What is a glycosidic bond?
- 6Units of lactose.
- 7Iodine test of starch.
- 8Where is glycogen stored?
Show answers (try them yourself first)
- 1α-Glu(1→2)β-Fru.
- 2+66.5° ⇒ –20°.
- 3Linear vs branched.
- 4No enzyme to cleave β links.
- 5A C–O–C link.
- 6Galactose + glucose.
- 7A blue colour.
- 8Liver and muscles.
Amino acids and peptides
Egg, pulses and milk contain proteins that are chains of amino acids.
α-Amino acids are H₂N–CHR–COOH and exist as zwitterions. Two amino acids lose H₂O to form a peptide bond.
In the figure : Amino acids and the peptide bond.
Rule 1: Classification — 20 standard amino acids; essential = the body cannot make them (valine, leucine, lysine); non-essential = it can (glycine, alanine).
- Easy : Glycine (R = H) is achiral.
- Medium : Others are mainly L.
- Exam-type : Essential ones come from diet.
Rule 2: Zwitterion and pI — H₃N⁺–CHR–COO⁻. pH < pI ⇒ cation; pH > pI ⇒ anion; pH = pI ⇒ net charge 0 (lowest solubility). Glycine pI = 5.97.
- Easy : In acid: H₃N⁺CH₂COOH.
- Medium : In base: H₂NCH₂COO⁻.
- Exam-type : Precipitation is easiest at the pI.
Rule 3: Peptides — n amino acids ⇒ (n – 1) peptide bonds + (n – 1) H₂O; di-, tri-, polypeptide (above ≈ 100 units = protein).
- Easy : 2 Gly ⇒ Gly-Gly + H₂O.
- Medium : 15.0 g Gly ⇒ 13.2 g dipeptide + 1.8 g H₂O.
- Exam-type : A tetrapeptide has 3 bonds.
Calculation: Gly-Gly from 15.0 g glycine
- Step 1: n = 15.0 ÷ 75.07 = 0.2 mol.
- Step 2: 2 Gly ⇒ 1 Gly-Gly ⇒ 0.1 mol.
- Step 3: M = 2×75.07 – 18.02 = 132.1 ⇒ 13.2 g.
CET level (MCQ)
- CET 1) Peptide bonds in a tetrapeptide? 1) 3 2) 4 3) 2 4) 5 — Answer: 1).
- CET 2) Achiral amino acid? 1) glycine 2) alanine 3) valine 4) lysine — Answer: 1).
Real-life use: Diet, drugs, supplements.
n units ⇒ (n–1) bonds; charge 0 at pI; glycine is achiral.
Writing n peptide bonds for n amino acids.
A linear chain has (n–1); a cyclic peptide has n.
Memory clue: "one more acid than bonds".
Spot the difference
| n | Peptide bonds | H₂O |
|---|---|---|
| 2 | 1 | 1 |
| 3 | 2 | 2 |
| 10 | 9 | 9 |
Practice questions
- 1General structure of an amino acid.
- 2What is a zwitterion?
- 3Write a peptide bond.
- 4Essential amino acids.
- 5Meaning of pI.
- 6Bonds in a pentapeptide?
- 7Why is glycine achiral?
- 815.0 g Gly ⇒ ?
Show answers (try them yourself first)
- 1H₂N–CHR–COOH.
- 2H₃N⁺ and COO⁻ in one molecule.
- 3–CO–NH–.
- 4Those the body cannot make.
- 5pH of zero net charge.
- 64.
- 7R = H.
- 813.2 g.
Protein structure, denaturation and enzymes
Cooking an egg turns the clear white opaque — protein denaturation.
Proteins have 1° (sequence), 2° (α-helix, β-sheet via H-bonds), 3° (3-D folding) and 4° (several chains) structure.
In the figure : Structure levels.
Rule 1: Structure levels — 1°: peptide bonds. 2°: C=O···H–N H-bonds. 3°: H-bonds, S–S, ionic, hydrophobic. 4°: assembly of subunits (e.g. haemoglobin).
- Easy : Keratin is α-helix.
- Medium : Silk is β-sheet.
- Exam-type : Haemoglobin has 4°.
Rule 2: Denaturation — Heat, acid/base, heavy metals (Hg²⁺), urea destroy 2° and 3°; 1° stays; activity is lost.
- Easy : Cooking an egg.
- Medium : Curdling of milk.
- Exam-type : Usually irreversible.
Rule 3: Enzymes — Biological catalysts (proteins): lower activation energy; specific (lock and key); optimum ≈ 310 K, pH ≈ 7 (pepsin ≈ 2).
- Easy : Amylase breaks starch.
- Medium : Urease breaks urea.
- Exam-type : Heating denatures enzymes.
Reasoning: why does heat stop an enzyme?
- Step 1: Heat breaks H-bonds.
- Step 2: 3° folding fails and the active site changes.
- Step 3: The substrate no longer fits so activity stops.
CET level (MCQ)
- CET 1) 2° structure arises from? 1) H-bonds 2) S–S 3) ionic 4) peptide — Answer: 1).
- CET 2) Which structure survives denaturation? 1) 1° 2) 2° 3) 3° 4) 4° — Answer: 1).
Real-life use: Digestion, drugs, detergents, cheese.
2° = H-bonds; denaturation keeps 1°; enzymes lower Ea, 310 K.
Thinking denaturation breaks peptide bonds.
Denaturation destroys 2°, 3°, but 1° remains.
Memory clue: "1° order, 2° fold, 3° shape, 4° team".
Spot the difference
| Level | Held by |
|---|---|
| 1° | peptide |
| 2° | H-bonds |
| 3° | S–S, ionic |
| 4° | subunits |
Practice questions
- 1Four levels of protein.
- 2α-helix and β-sheet.
- 3What is denaturation?
- 4How do enzymes work?
- 5Optimum temperature.
- 6Haemoglobin's level?
- 7Level with S–S bonds?
- 8Lock-and-key model.
Show answers (try them yourself first)
- 11° 2° 3° 4°.
- 2Two kinds of 2°.
- 3Loss of 2°/3°.
- 4By lowering Ea.
- 5≈ 310 K.
- 64°.
- 73°.
- 8Substrate fits the active site.
Nucleic acids: nucleotides, DNA and RNA
Children inherit parental traits because of information stored in DNA.
Nucleotide = base + pentose sugar + phosphate. DNA: 2-deoxyribose, A G C T. RNA: ribose, A G C U.
In the figure : DNA and RNA.
Rule 1: Components — Purines: A, G. Pyrimidines: C, T, U. Nucleoside = base + sugar; nucleotide = + phosphate; linkage: phosphodiester.
- Easy : T in DNA; U in RNA.
- Medium : Two rings: A, G.
- Exam-type : One ring: C, T, U.
Rule 2: DNA double helix — Two complementary strands: A=T (2 H-bonds), G≡C (3 H-bonds); %A = %T and %G = %C (Chargaff).
- Easy : A = 30 % ⇒ T = 30 %, G = C = 20 %.
- Medium : 100 pairs (30 A–T + 70 G–C) ⇒ 270 H-bonds.
- Exam-type : G–C pairs are more stable.
Rule 3: Types of RNA — mRNA (message), tRNA (carries amino acids), rRNA (ribosomes). DNA ⇒ RNA ⇒ protein (transcription, translation).
- Easy : DNA replication.
- Medium : tRNA anticodon.
- Exam-type : Three bases = one codon.
Calculation: H-bonds in a 100-pair DNA piece
- Step 1: 30 A–T pairs × 2 = 60.
- Step 2: 70 G–C pairs × 3 = 210.
- Step 3: Total 60 + 210 = 270.
CET level (MCQ)
- CET 1) Base absent from RNA? 1) thymine 2) uracil 3) adenine 4) guanine — Answer: 1).
- CET 2) H-bonds in G≡C? 1) 3 2) 2 3) 1 4) 4 — Answer: 1).
Real-life use: DNA fingerprinting, drugs, vaccines.
A=T 2; G≡C 3; DNA has T, RNA has U; deoxyribose.
Writing thymine for RNA.
DNA = 2-deoxyribose; RNA = ribose (OH at 2').
Memory clue: "A-T two, G-C three".
Spot the difference
| Feature | DNA | RNA |
|---|---|---|
| Sugar | deoxyribose | ribose |
| Bases | A G C T | A G C U |
| Strands | two | one |
Practice questions
- 1What is a nucleotide?
- 2DNA vs RNA.
- 3Chargaff's rule.
- 4A = 30 % ⇒ G?
- 5Purines and pyrimidines.
- 6Types of RNA.
- 7Phosphodiester linkage.
- 8Why can DNA replicate easily?
Show answers (try them yourself first)
- 1Base + sugar + phosphate.
- 2Sugar, T/U, strands.
- 3A = T, G = C.
- 420 %.
- 5Two rings vs one ring.
- 6m, t, r.
- 7Joins sugar and phosphate.
- 8Complementary pairing.
Quick revision of the whole lesson
| Concept | Key formula / fact |
|---|---|
| Glucose | aldohexose, 16 isomers |
| Anomers | differ at C-1; +52.7° |
| Sucrose | non-reducing; +66.5° ⇒ –20° |
| Peptide | n ⇒ (n–1) bonds |
| pI | net charge 0 |
| Denaturation | 2°, 3° lost; 1° stays |
| DNA pairs | A=T (2), G≡C (3) |
| RNA | ribose, U, single strand |
🚀 Quick revision of the whole lesson
In the app you can move this figure with your finger.
Open in the app🎯 Most important points for the exam
- Classification.
- Glucose structure.
- Ring, anomers.
- Di/polysaccharides.
- Amino acids, peptides.
- Proteins, enzymes.
- DNA, RNA.
understand the idea → remember the formula → solve the example → solve problems yourself.