CHEM 222 Lecture Notes - Lecture 5: Pi Bond, Benzene, Activation Energy
28 Sep 2020
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Problem 4. 1: arrows and intermediates added below, the mechanism below shows a strong base attacking a secondary halide to give an ether from an sn2 pathway. Although there are technically no errors in the arrows or intermediates, this would not be the major product, as e2 would be favoured. Problem 4. 2: see below, the major product (cationic/sn1 pathway) comes from the most stable intermediate (lowest activation energy barrier, fastest reaction, most preferred pathway). Thus, protonation followed by an sn1 style reaction is a lower energy pathway than sn2. In the sn2 style reaction, an oxyanion needs to be generated, which is extremely unflavoured under acidic conditions. (no. Reactive anions in acid; no reactive cations in base) Problem 4. 3: completed transformations are below, alkenes and alcohol products, alkenes and epoxide products, products for alkene oxidations: Problem 4. 4: multi-step synthesis products, synthetic pathways: From 13c nmr spectrum of compound b: 8 signals, at least 8 carbons.
