6) Give the structures of the compounds A-E in the synthetic sequences below. PBr3, Br2 NH3, excess LOH A B you 1) NaNH2 (1 equiv) H2O, HgSO4 Br2 excess HCECH C D E H2SO4 NaOH excess 2) BuCI (1 equiv)

CH3CH2CHCH2CH3 CH3CH2CHCH2CH3 2. NACN 3. H3o* (b) _CH2CO2H CH2CH3 1. LIAIH 2. H30* (c) он он CH3CH2CH2CI ČH3 1. NaCN 2. H30* CH3CCH2CH2COH ČH3 2. Identify the missing reagents a-f in the following scheme: Br CO2H CHO

7) Predict the major products of the following reactions, including stereochemistry where appropriate. DRAW the detailed structure of those products. a) sec-butyl isopropyl ether + concd. HBr / A b) ethyl phenyl ether + concd. HI / A c) trans-2,3-epoxyoctane + H₂O / H₂SO4 d) methyl phenyl ether + 1) BBr3 / THF 2) H₂O h) 1,2-epoxyhexane + CH₂OH / H₂SO4 i) epoxypropane + excess CH3NH2 j) potassium tert-butoxide + 1-bromobutane k) cis-2,3-epoxyoctane + HCl / Et₂O

What is the major product of the reaction sequence shown in the box? OCH3 Pd-cat HCI NaNO2 KI ? Base Fe H2SO4 ОН -B' ОН NO2 A) B) OCH3 -OCH3 NO C) D) O,N- -OCH3 -OCH3 A В

9 4 points 1) CI AICI 3 2) MgBr 3) H+/H₂O Predict the final product of the reaction sequence shown above.

Chem. q4 b i