Question

Molecule A (1.4.7-trimethyloxatriquinane) is a three-fold, tertiary alkyl oxonium salt. The compound is inert to solvolysis with alcohols, even at elevated temperatures, but it readily undergoes substitution with the strongly nucleophilic azide anion (N) in chloroform (CHCI), polar aprotic solvent). An S, 2 pathway is the only reasonable mechanistic interpretation for this reaction, despite the fact that substitution is occurring at a tertiary carbon center (a) is the product chiral? (0.2 pts) (b) Describe three features of this reaction that make an S, 2 pathway feasible. Note the 3-dimensional, ball- and-stick drawing of molecule A below. (0.3 pts) chiral? (yes) (no) CHCI molecule A 8. Circle the compound in each pair that would react faster with the indicated reagent system. (0.6 pts Nal, acetone S2 NaOCH, CH, OH CH,CH, OH S1/E1

Answer 1

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