Alkenes can be converted to alcohols by hydroboration‑oxidation. Draw the structure of the alcohol or alcohols formed in the rea
ction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in‑plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge‑and‑dash bonds.
1 answer:
Hydroboration-oxidation is a reaction which follow anti markonikov orientation.
The stereochemistry of hydroboration-oxidation follows syn-adition being a stereospecific reaction. That means that boron and hydrogen are added from the same side. Then, when the oxidation occurs, the boron is replaced by an hydroxyl having the same geometric position.
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Alkenes on reacting with ozone results in the formation of ozonide which undergo reductive cleavage in presence of dimethyl sulfide to form carbonyl compounds (aldehyde or ketone). Whereas in presence of hydrogen peroxide it undergoes oxidative cleavage to form carboxylic acids or ketones.
Since, A alkene yields 4-heptanone only on treatment with ozone and DMS thus, it implies that both the chains on the side of the double-bond are similar the product is 4-heptanone that means the double bond is present between the chains at the 4th carbon. Therefore the structure of compound A is 4,5-dipropyloct-4-ene.
The reaction is as shown in the image.
The reaction of A with m-CPBA (meta-perchlorobenzoic acid) followed by aqueous acid is shown in the image.
m-CPBA (meta-perchlorobenzoic acid) is a peracid and forms epoxides on reacting with alkenes.
