SUNCOI Stellenbosch University Chemistry Outreach Initiative in collaboration with the WCED1 FORMAL ASSESSMENT: TASK 1 Experiment: Preparation of esters Teacher’s Memorandum [1] MZ Moerat, Subject Advisor Physical Sciences, Western Cape Education Department, mmoerat@pgwc.gov.za PLANNING [10 marks] Listing chemicals: All alcohols correct: All carboxylic acids correct: Catalyst correct: Methanol, Propanol, Pentan-1-ol Salicylic acid, ethanoic acid, butanoic acid Concentrated Sulphuric acid/Conc. H2SO4 (1) (1) (1) Drawing apparatus: 1/2 mark for each correct label: 1. 2. 3. 4. 5. 6. Bunsen burner tripod/gauze alcohol/carboxylic acid/sulphuric acid test tubes beaker /water bath thermometer All the apparatus is drawn correctly in the set-up (1) 6 Appropriate labels indicated correctly (3) Identification of variables One mark for each correct variable: Independent – Type of alcohol and carboxylic acid used. Dependant - Smell/Type of ester prepared Controlled - amount of reactants used/accept other applicable answers (3) RESULTS [15 marks] Table (One table summarizing all the results): Acid and Alcohol Reacted Salicylic Acid and Methanol Ester Product Odour detected Methyl 2-hydroxybenzoate Oil of wintergreen/menthol Ethanoic acid and Propanol Propyl ethanoate Pear Ethanoic acid and Pentanol Pentyl ethanoate Banana Buthanoic acid and Methanol Methyl butanoate Apple Table heading is appropriate (1) 2 Column headings are appropriate (2) Data is appropriate, accurate and correct (3) Balanced chemical equation for each reaction (B to D): PART B: H O H H H H O H H H H | || | | | | || | | | | H–C–C–O–H + H–O–C–C–C–H → H–C–C–O–C–C–C–H + O–H | | | | | | | | H H H H H H H H PART C: H O H H H H H H O H H H H H H | || | | | | | | || | | | | | | H–C–C–O–H + H–O–C–C--C--C–C–H → H–C–C–O–C–C–C--C--C–H + O–H | | | | | | | | | | | | H H H H H H H H H H H H PART D: CH3CH2CH2COOH + CH3OH → CH3CH2CH2COOCH3 Three marks for each correctly balanced equation. (9) CONCLUSIONS/EXPLANATIONS: [10 marks] 1. The reactants are flammable. The water bath prevents direct contact with the flame in the case of spillage. (2) 2. The excess reagents (alcohol and carboxylic acid) will dissolve in water, while the product (ester) does not. (2) 3. The reactants have lower boiling points than water. (1) 4. Catalyst (1) 5. (Any one) Safety goggles Lab coat Gloves Use well-ventilated room or in fume cupboard. Wash off any contacted area immediately with large amounts of cold water. Ethanoic acid is flammable, caustic and cause burns. Do not inhale. Pentanol and ethanol is flammable, use a water bath. Do not get in contact with the sulphuric acid. Methanol is highly flammable and toxic if it is inhaled or swallowed. 6. Esterification (1) (1) 7. (Any One) 3 Making perfumes Making air fresheners Making drinks Making baking/ food colorants Used by animals for hunting Used to identify partners for mating (1) TOTAL MARK /35/ TEACHER’S NOTES: Order reagents and apparatus well in advance. (You may contact B & M Scientific, SigmaAldrich, Kimix, Merck and Lasec or any other supplier for the cheapest quote). Ensure that learners are well aware of the safety precautions for this experiment. The reagents used in this task may be replaced with any other available alcohol or carboxylic acid. The “Additional Esters Hand-out” contains four other possibilities which may be used as replacements. (The preparation with butanoic acid leaves an unpleasant smell in the classroom.) Many esters have very similar smells. Choose esters with distinctive smells if possible. (See attached list of esters). Make use of IUPAC names as far as possible when setting the task. The current prescribed text book uses some general names (e.g. acetic acid for ethanoic acid) in their practical, so add these names to your memos. 4