Question: Draw the products formed when each alkene is treated with followed by . Include the stereochemistry at all stereogenic centers.
This reaction consists of two steps: hydroboration and oxidation. It gives a racemic mixture of alcohols.
The reaction of but-1-ene with followed by oxidation is shown below:
Product formation in a
The reaction of (S)-1,4-dimethylcyclohex-1-ene with followed by oxidation is shown below:
Product formation in b
The reaction of 1-ethylcyclopent-1-ene with followed by oxidation is shown below:
Product formation in c
Question: Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl , forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation— to a double bond.
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