Question

1. Propose a synthesis for either of the following molecules using the indicated starting materials. You don't have to use all of them, but all your carbon atoms must come from them alone. (Hint: A five membered lactone will spontaneously form from the correct hydroxy acid.) If you provide syntheses for both a 10 pt bonus will be awarded. OH со, КCN Br н Н NO, Br NH2 2. Propose a mechanism to account for the following reaction. Used the curved arrow formalism and draw the structure of all intermediates. Your mechanism must clearly show the catalytic role for the strongly nucleophilic, but weakly basic amine (pKaHA 8.8) D оHO (cat) 1

Answer 1

to Symnesis gi ven- forward Synthel base Br kactonisatton mild ducing gen Fimai product

NO Forward Synpaeses Nao HC Br BY NH2 NHL NH2 n/ dic BT BY BT Br 1NaaoMc preducct (Fmai BT ME

Mechanism for Jue -conveysian Mechanism он Fimal Predeuc