Chem 220a Problem
Set 9 Fall 2003
(a) aqueous HBr, heat
(b) HNO3
(c) NaH, THF
(d) CrO3, pyridine, HCl
(e) p-toluenesulfonyl chloride, pyridine
(f) propylmagnesium bromide
(g) SOCl2, pyridine
(h) product of (a) + Mg in ether
(i) product of (e) + t-BuO-K+ in t-BuOH
(a) 2-deuterio-2-methylpentane from 2-methylpentan-2-ol
(b) 2-methylpent-1-ene from 2-methylpentan-2-ol
(c) PhCH2CH2Br from bromobenzene (PhBr)