Question

1. Provide conditions for the following reactions. More than one step may be needed. Incorporate conditions that would give you the optimum yield, and be mindful of stereochemical details. (4 pts each) a. H F b. но OH

Answer 1

a) The alkylation of the theophylline using two conditions (1.- n-tributyl phosphate/NaOH and 2. n-butyl bromide/NaH/DMF) mentioned as below give the good yield of the final product as shoen in the below image.

b) Here the product formation is two step process, first epoxidation of Z-cis alkene as reactant to get epoxide which is converted into next step by opening using base like NaOH to get corresponding product as always trans vicinal diol as product 1 and product 2. The exact stereochemistry of both the products have been labelled in the drawn structure as below

Page N Date nihattpPagphet OnBu nbubnbe Naed My0 Theophyline Yeild -80-90 NaH DMF BY nlathuylhe Yrdd 780

Page No Dete MCРВА Epoxidahian Ztis allene rudant Opereng gipac Ио, H Trans icinal dut frdueto the oletin udergo eppealin using mer ehlonpereny benzie au te tom deonde the eporide t anti tashine waay basi Carethin ENae) is to get tans-hydnylection Probiuct 15 R) tans diol otint (RS) toaus didl