Question

Please help with A-H

Apply retrosynthetic analysis to guide the preparation of each of the following compounds from the indicated starting material, then write out the synthesis showing the necessary reagents. (a) 1-Propanol from 2-propanol (b) 1,2-Dibromopropane from 2-bromopropane (c) 1-Bromo-2-propanol from 2-propanol (d) 1-Bromo-2-methyl-2-propanol from tert-butyl bromide (e) 1,2-Epoxypropane from 2-propanol (1) tert-Butyl alcohol from isobutyl alcohol (g) tert-Butyl iodide from isobutyl iodide

Answer 1

(a) Cone H₂SO4 CH₂ - CH - CH₂ - CH₂-CH=CH2 СИ Pro Реме Jj B ₂ HG . THE сі» ,0, Jory сна - Сн,— си, от Рxbean ) -о) alcokoh (5) СА, - Сң- си — сне — сH = си, Вх emen, 2. Bromopropane. Вх 3х 1,2-dibromopropane Br2 ewater Char CH-CH2 conc. H₂ SOy (c) сH, - си-си; CH₂ – CH=CH₂ Вт, +н, о CH 2- рю рама | CH₂ CH-CH₂ OH Br ) - Дm my - 2-р хороо 4.

CM3 (d) Chyn & - CH3 alcikoy d C- alcokon CH 3 Chan Chan -do CH2 2-methyl-proplane tentabutyl bromide Bry +H₂O CHgCr CH2 on br 1-Bromo-2-methyl-2-pr (e) CH₂ - CH CH₂ propene. conc. H₂SO4 CH₂ - CH=CH₂ Ag20 CHgn CH - CH2 0 1,2-Epoxypropane a-propanol СИ (f) . CH₂ - CH-CH₂-OH iso butyl alcohol conc. H₂SO4 CH3 CHAĆ - CH₂ Domethyl-prop-Irene Kail Ht or H₂ot } CH3 CH₂nd-cha On text 2-methyl-propane aro) butyl alcohol os

CH3 CH3 (7) ROM I alco CH₃-CH-CH₂ iso-butyl iodide > CH₃ - CH = CH2 JHI CH₂- & - CH3 tert-butyl iodide. ch alcokoll cyclohexene. cyclohexyl chloride Cl₂ + H₂O ce nou trans-2-chloro cyclohexanol