1) You react (E)-27-dimethyl-4-octene with bromine collect product and then perf

1) You react (E)-27-dimethyl-4-octene with bromine collect product and then perform a second reaction with potassium hydroxide.
OChem Worksheet
1) You react (E)-27-dimethyl-4-octene with bromine collect product and then perform a second reaction with potassium hydroxide.
a) Show the entire mechanism for these reactions. (10pts)
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. (12pts)
c) Given the following melting point data for the intermediate and product briefly comment on purity. (intermediate: 166-170C product: 145-155C) (3pts)
2) Acetone and propanal react via an aldol condensation in the presence of sodium hydroxide. Show the four possible products and the mechanisms that lead to each one. (20pts)
3) You wish to synthesize 11-diphenyl-1-propanol via Grignard technique. 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. Briefly comment as to which is the more desirable synthetic pathway. (15pts)
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