2. Suggest synthetic routes to the following using the indicated starting materials (2a and 2c will all have been covered in lecture, the other problems are from Chapter 24, all use chemistry that had been covered in Chemistry 227). a. R-2-aminobutane from S-2-butanol (all four carbons must come from butanol - remember E2 can be a problem with a simple amine as a nucleophile with a secondary substrate) b. pentanoic acid from 1-butene from Et NH and any alkene d. 1,6-hexandioic acid from cyclohexanol f. HO₂C HO₂C COH from cyclopentadiene (think about Chapter 19 chemistry and alkene chemistry from way back in Chemistry 227) CHCOH

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