1) You react (E)-2,7-dimethyl-4-octene with bromine, collect product, and then perform a second reaction with potassium hydroxide. a) Show the entire mechanism for these reactions. b) Given the following masses for starting material, intermediate, and final product (2.0g/4.26g/1.66g) calculate the percent yield for step 1, step 2, and the overall reaction. c) Given the following melting point data for the intermediate and product, briefly comment on purity. (intermediate: 166-170C, product: 145-155C) (2pts) 2) Acetone and propanal react via an aldol condensation in the presence of sodium hydroxide and then heat. Show the four possible products, and the mechanisms that lead to each one. 3) You wish to synthesize 1,1-diphenyl-1-propanol via Grignard technique. a) Show two possible synthetic pathways, along with their mechanisms. One of them should involve a ketone or aldehyde as a substrate, and the other should involve an ester substrate. Make a claim as to which is the more desirable synthetic pathway. b) Show what would happen if your Grignard reagent came into contact with water. For this reason, what precautions must be taken when performing a Grignard reaction? 4) What is the difference between an s-cis and s-trans diene? Which can undergo Diels-Alder cycloadditions and why?
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