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Synthesizing Organic Compounds – Practice
Note: The questions are taken from the Nelson Chemistry 12 textbook.
Nelson (2003). Synthesizing Organic Compounds, Chemistry 12 (pg. 82)
1. A food additive that is named as a single ingredient is often a mixture of many compounds. For
example, a typical “artificial strawberry flavour” found in a milkshake may contain up to 50 different
compounds. A few of these are listed below. For each, write a structural formula and an equation or a
series of equations for a method of synthesis from the suggested reactants.
(a) 2-pentyl butanoate from pentene and butanal
(b) phenyl 2-methylpropanoate from phenol and an appropriate alcohol
(c) 4-heptanone from an alcohol
(d) ethyl ethanoate from ethene
2. For each product, write a structural formula and an equation or a series of equations for a method of
synthesis from other compounds.
(a) pentyl ethanoate from ethene and an alcohol
(b) phenyl ethanoate from an alkene and an alcohol
(c) 3-octanone from a simpler compound
(d) methyl benzoate from two alcohols
(e) sodium salt of butanoic acid from an ester
(f) trimethylamine from ammonia and alkanes
(g) N-ethylethanamide from an alkane and ammonia
3. The smell of freshly cut grass can be simulated by the addition of hexanal to substances such as airfresheners. Describe how hexanal can be made from an alcohol.
4. In artificial apple flavour, the main ingredient is ethyl 2-methylbutanoate.
(a) Draw a flow chart to show the synthesis of this compound, starting with simpler compounds.
(b) Describe the steps in the procedure for this synthesis. Include experimental conditions and safety
precautions in the handling and disposal of materials.
5. The flavour of almonds is obtained from phenyl methanal, also called benzaldehyde. “Natural”
almond flavour is extracted from the pit of peaches and apricots, and may contain traces of the poison
hydrogen cyanide.
(a) Write a structural diagram for benzaldehyde.
(b) Write equations for a series of reactions in the synthesis of benzaldehyde from an ester.