Chemistry of Cooking and Oxidation Higher Supported Study Week 3 – Part 2 Chemistry of Cooking – Key Areas • • • • • Shapes of Proteins Denaturing of Proteins Flavour and Aroma Molecules Aldehydes and Ketones Tests to differentiate between Aldehydes and Ketones • Effect of functional groups and properties Shapes of Proteins • Spirals, Sheets, complicated shapes • Held in these shapes by intermolecular bonding Heating Proteins (Cooking) • Intermolecular bonds are broken allowing the proteins to change shape (denature). • These changes alter the texture of foods. • New intermolecular forces form Flavour and Aroma Molecules • Many flavour and aroma molecules are ALDEHYDES Aldehydes Functional Group Carbonyl (C=O) END OF MOLECULE - al endings Naming Aldehydes Ketones Functional Group Carbonyl (C=O) Ketone C=O found in middle of molecule -one ending Aldehydes and Ketones • Can be named from structural formulae. • Structural formulae can be drawn from names • Molecular formulae can be written from names • Isomers can be drawn Aldehyde Tests Three possible tests to determine if substance is aldehyde or ketone Oxidising Agents 1) Fehling’s Solution ( Blue brick red precipitate) 2) Acidified potassium dichromate (orange green) 3) Tollen’s Reagent (colourless a silver mirror) Must be warmed in a water bath Aldehydes Oxidise (Ketones don’t) Intermolecular Forces Properties High boiling points • STRONG INTERMOLECULAR FORCES High Volatility (how easily it evaporates) • WEAK INTERMOELCULAR FORCES • SMALL MOLECULAR SIZE SOLUBILITY • LIKE DISSOLVES LIKE 32. C7H6O2 → C7H8O Which line in the table is correct for the above conversion? Reaction type A reduction B reduction C oxidation D oxidation H:O ratio increases decreases increases decreases 27. The compound structure CH2CHCH2CHO is A B C D with a saturated ketone a saturated aldehyde an unsaturated ketone an unsaturated aldehyde. the 6. The molecules shown below are isomers A B a) Name each of the isomers. A - butanal B – butanone b) Which isomer can be oxidised using Tollens’ reagent and what would be observed? Isomer A (butanal) is oxidised using Tollens’ reagent A silver mirror forms (since the silver ions are reduced to silver atoms) 8. Which type of bond is broken when a protein is denatured? A B C D Ionic Polar covalent Hydrogen Non-polar covalent C Oxidation of Food • • • • • • • • • • Naming branched chain alcohols Primary, secondary and tertiary alcohols Isomeric alcohols Hydrogen bonding of alcohols Diols and Triols Oxidation of alcohols Naming branched chain carboxylic acids Reactions of carboxylic acids. Antioxidants in foods. From an ion-electron equation recognise that a substance is acting as an antioxidant. Naming branched chain alcohols • Functional Group (hydroxyl) always gets first priority when numbering longest carbon chain What SQA expect you to be able to do: • Can be named from structural formulae • Structural formulae can be drawn from names • Molecular formulae can be written from names Primary, secondary and tertiary alcohols Primary – Carbon to which hydroxyl group attached is bonded to 2 or more hydrogens or is bonded to 1 carbon Primary, secondary and tertiary alcohols Secondary – Carbon to which hydroxyl group attached is bonded to 1 hydrogen or is bonded to 2 carbons Primary, secondary and tertiary alcohols Tertiary – Carbon to which hydroxyl group attached is bonded to 0 hydrogen or is bonded to 3 carbons 10.a) Name the following alcohols and decide whether they are primary, secondary or tertiary alcohols. 10.a) Name the following alcohols and decide whether they are primary, secondary or tertiary alcohols. Pentan-2-ol 2ry Pentan-3-ol Note: These alcohols are all ISOMERS 2-methylbutan-2-ol 3ry 2ry 2,2-dimethylpropan-1-ol 1ry Isomers Draw the structural formula for, and name isomeric alcohols, including primary secondary and tertiary alcohols Question Name each of these alcohols. State for each whether it is Primary, secondary or tertiary Which type of chemical reaction could be used to distinguish which was which? Diols and Triols • The more hydroxyl groups • The Stronger the H-Bonding • The Higher the Boiling Point • The Lower the volatility (doesn’t evaporate easily) • The Higher the Viscosity(the thicker the liquid appears) • More Viscous – less likely to dissolve in H2O (immiscible) 11. The alcohols shown below have similar molecular mass, considering their structure comment on the viscosity and boiling point of the molecules pentan-1-ol butane-2,3-diol propane-1,2,3-triol Increasing the level of hydrogen bonding will make the molecule have a higher boiling point and more viscous. Propane-1,2,3-triol will have the highest boiling point and greatest viscosity, then butane-2,3-diol and lastly pentan-1-ol. Oxidation of alcohols Aldehydes Oxidise (Ketones don’t) 27. Which of the following would not react with acidified potassium dichromate solution? A B C D Methanol Methanal Butanone Butan-2-ol Naming branched chain carboxylic acids Reactions of carboxylic acids. • reduction in terms of products and effect on the oxygen to hydrogen ratio • reactions with bases to form salts • reaction with alcohols to form esters Reduction of Carboxylic Acids Reactions with bases to form salts Bases include Metal Oxides Metal Hydroxides Metal Carbonates 12. (i) Name the functional group circled below. carboxyl (ii) Draw a structural formula for the organic compound formed when the above compound reacts with NaOH(aq). (zero) Antioxidants in foods Oxygen reacts with edible oils giving the food a rancid flavour. Antioxidants are molecules which will prevent these oxidation reactions taking place. Making Food Last Longer Potatoes are typically fried under an atmosphere of steam and packaged under nitrogen. 15. Vitamin C, C6H8O6 is an antioxidant. (i)What is the purpose of adding antioxidants to food? To increase shelf life (stop it going off) (ii) Complete the ion-electron equation for the oxidation of vitamin C. C6H8O6(aq) C6H6O6(aq) +2H+ + 2e-