8303147-053-Organic-Synth-Ques

8303147-053-Organic-Synth-Ques - Chem Factsheet April 2003...

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Answering Questions on Organic Synthesis C hem F actsheet April 2003 Number 53 1 Before working through this Factsheet you should: Have a good knowledge of the organic chemistry covered at AS and A2 level; Have a good knowledge and understanding of the reagents and conditions required to interconvert organic functional groups; Have worked through the organic chemistry Factsheets. After working through this Factsheet you will: Have been shown the two common types of organic synthesis questions. Have more experience in answering questions on organic synthesis. You may find it useful to have Factsheet 52 ( reactions of funtional groups) besides you when you work through this Factsheet. There are two common types of exam questions on organic synthesis. Factsheet 35 has covered the first, more straightforward, style of question. It involves the conversion of functional groups from one type to another. For example, given the reaction scheme: CH 3 CH 2 CH 2 Cl CH 3 CH 2 CH 2 OH CH 3 CH 2 COOH CH 3 CH 2 COCl A B C D The examiner may test candidates’ knowledge of organic reactions by asking for reagents and conditions, or even equations. Step 1: CH 3 CH 2 CH 2 Cl + NaOH CH 3 CH 2 CH 2 OH + NaCl Conditions: Aqueous, heat under reflux Step 2: CH 3 CH 2 CH 2 OH + 2[O] CH 3 CH 2 COOH + H 2 O Conditions: K 2 Cr 2 O 7 , acidified with conc. H 2 SO 4 Step 3: CH 3 CH 2 COOH + PCl 5 CH 3 CH 2 COCl + HCl + POCl 3 Conditions: Dry. The second, more difficult, style of organic synthesis question requires candidates to produce their own reaction scheme, or ‘flow chart’. Using the above example, candidates may be supplied with less information. For example, devise a reaction scheme involving several steps to convert
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8303147-053-Organic-Synth-Ques - Chem Factsheet April 2003...

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