Question

1. Predict the product(s) (or no reaction) and reagent(s). (31 pts; no partial point)

1. PBr3, Etz0 2. NaCN NaH ཉེ - ༈ ༈ ཙ ཚེ ན HBr 0 °c HzSO4 heat

Answer 1

O-H () OPBus, Ebo No CN Mechanism: SNI followed by SN HBO RS - (o=p-By In Inta molecular cleophilic substitution, nucleophile approaches from sane e-side as leaving group. so in this SN Leaving group & nucleoptile ale in Same side. So setention op stereochemi! EN attackx on Br Carbon containing Bratom from the side opposite to Bratom. so this is SN² mechanism UCN

Na 14 -TS - Na-o-ts) Mechanism DEWO H 30 O= +88-3 cheo This reaction occurs through the formation of stable to cantoration intermediate by Wagner - Meervin rearrangement: TH in B 4 B D 12 zo Carbocation

so this is a sn mechanism as Volves Corbo cation intermediate. Hason, Ha soq a heat 0-H Mechanism: This also involves the formation op stable Costbocation inteymediate by the Wagner-Meervin rearrangement THIS ISE' elimination reaction. acid catalysed dehydration # - o- tot 80-H # 1,2 CH, shist na 2 Carbocation Haa