CHM255 – Homework Assignment 4

CHM255 – Homework Assignment 4Assigned Dec. 3 2014. Due at the beginning of class on Dec. 10 2014. Late homeworkswill not be accepted. Provide your answers on a separate sheet.1. Provide the missing products or reaction conditions. Wherever appropriate include a clear depiction ofstereochemistry.2. Propose a synthetic scheme to prepare each of the following products from the indicated starting material. Youranswer should consist of a sequence of two or three steps and include both the intermediate compounds as wellas the reaction conditions for each step. 3. (a) Provide the optimal alcohol and alkyl halide starting materials to prepare the product below via theWilliamson ether synthesis.(b) Propose synthetic schemes (may involve multiple steps) to prepare the alcohol and alkyl halide from alkenestarting materials. Your answer should include both the intermediate compounds as well as the reactionconditions for each step.4. Provide an arrow-pushing mechanism for the reaction below. Explicitly include all formal charges. For each step label the nucleophile/electrophile or acid/base as appropriate.5. (a) Provide the structure of the epoxide intermediate and diol final products for each reaction sequence below.Carefully depict the stereochemistry of each compound(b) Label each epoxide and diol compound as either chiral or achiral.