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?