Question

37oo 10 April 3, 2015 mpi ete the fol am 3 9 reactions. Show stereochemistry when relevant. (25 pts) CH Na N3 H3 CH3CN H, CH. CH S- Na DMSO Br Na -OCH 2CH3 CH3 CH3CH2OH, 50°C products (circle the major product) 1. Complete stereochemistry when (18 pts) the following reactions. Show OH PCC CH2Cl2 OH H2SO4 heat OH 2 K OH PBr3 ether OH 1. NaH 2. CHaCH2CH2Br 1. NaBHA, CH3OH 2. H30 12. You get five points. (5 pts)

Please help me answer questoions 10 and 11. My teacher does not provide an answer key. Explanations and tips to learn/master these types of problems would be appreciated.

Answer 1

M 3700 Complete the following reactions. 3, 2015 Exam 3 Show stereochemistry when relevant. (25 pts) он CH (Reaction proceeds via Carbocation H20 CH3 OH intermediate SN1 reaction mechanism) Br N3 Na CHVC N 、CH, (SN2 mechanism) ose︿ 뽀뽀 H,CH3 (SN2 Mechanism) DMSO Br Na" OCH2CH CH3CH2OH, 50°C (E, elimination proceeds via stable tertiary carbocation intermediate) снз two products (circle the major product) 11. e the following reactions. Show stereochemistry when relevant. (18 pts) OH PCC CH2Cl2 Oxidation of alcohol) OH H2SO heat (elimination) он OK 2 Ko A (formation potassium salt) он Br PBr3 ether (Halogenation of Hydroxy to halo alkane) он OCH2CH2CH3 2. CH3CH2CH2Br (NaH will abstract acidic proton from OH and nucleophilic oxygen will substitute alkyl halideo OH 1. NaBH4, CH3OH 2. H3O (reduction of keto to alcohol) 12. You get five points. (5 pts)