☰ Contents · Chemistry (Organic chemistry)

Carbohydrates. Monosaccharides

Lessons 30 · 1 lessons · A. Mutalibov, E. Murodov, S. Masharipov, H. Islomova. Organic Chemistry, Grade 10, 1st edition. G‘afur G‘ulom Publishing House, Tashkent, 2017
30

Carbohydrates. Monosaccharides: preparation and properties

Textbook: pp. 117–125
GoalExplain the classification of carbohydrates and the structure, properties (qualitative tests, fermentation) and importance of glucose and fructose.
New words
carbohydrates · uglevodlarmonosaccharides · monosaxaridlarglucose · glukozafermentation · bijg‘ish
Explanation

Carbohydrates are widespread in nature; the first ones studied fitted the formula Cₙ(H₂O)ₘ, hence the name. By structure they are divided into monosaccharides (not hydrolyzed: glucose, fructose, ribose), disaccharides (give two monosaccharides on hydrolysis: sucrose, maltose) and polysaccharides (starch, cellulose). A monosaccharide name is the carbon count plus “-ose”: hexoses C₆H₁₂O₆, pentoses C₅H₁₀O₅. In open form glucose is CH₂OH–(CHOH)₄–CHO — an aldehyde alcohol (one –CHO and five –OH); in solution it is in equilibrium with six-membered ring α- and β-forms. Fructose is its isomer, a ketone alcohol (it has a >C=O group), and is sweeter; glucose decolourizes bromine water while fructose does not — one way to tell them apart. Glucose is a sweet, colourless crystalline solid, very soluble in water. Thanks to the aldehyde group it gives the “silver mirror” and Cu(OH)₂ (red Cu₂O on heating) tests; as a polyhydric alcohol it turns Cu(OH)₂ into a blue solution; hydrogen reduces it to sorbitol. It ferments under enzymes: alcoholic fermentation C₆H₁₂O₆ → 2C₂H₅OH + 2CO₂. In green plants glucose forms in photosynthesis: 6CO₂ + 6H₂O → C₆H₁₂O₆ + 6O₂ (light, chlorophyll); in the body it is slowly oxidized to release energy: C₆H₁₂O₆ + 6O₂ → 6CO₂ + 6H₂O.

Worked examples
180 g of glucose (1 mol) in alcoholic fermentation gives 2 mol of ethanol, i.e. 92 g, and 2 mol of CO₂ (88 g). In the silver mirror test 180 g of glucose releases 2 mol of Ag, i.e. 216 g.
Photosynthesis: 264 g of CO₂ (6 mol) gives 1 mol of glucose, i.e. 180 g. Complete oxidation of 180 g of glucose needs 6 mol O₂ = 192 g of oxygen.
Class activity

Find “carbohydrates”, “sugars” and “fibre” on food packages and list which are monosaccharides (glucose, fructose) and which disaccharides (sucrose). Do not burn or heat anything.

Practice
1
What are the molecular formula and functional groups of glucose?
2
How many grams of ethanol (M = 46) form from the alcoholic fermentation of 180 g of glucose (M = 180)?
3
How many grams of silver does 180 g of glucose give in the silver mirror reaction (Ag = 108)?
4
Although glucose and fructose have the same formula, why are they compounds with different functional groups?