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Magazine Chapter 8: Q46E (page 262)
Question:What product will result from hydroboration鈥搊xidation of 1-methylcyclopentene with deuterated borane,? Show both the stereochemistry (spatial arrangement) and the regiochemistry (orientation) of the product.
Short Answer
Answer
The product of the reaction is:
Step by step solution
Regiochemistry and stereochemistry of Hydroboration- Oxidation
In this reaction, the hydrogen added o the double bond, will come from the Borane.
In hydroboration- oxidation reaction addition of hydroxide group is according to anti- Markovnikov鈥檚 rule i.e. OH group will be attached on the carbon atom having more number of hydrogens or we can say that it will be added on that carbon atom which is less substituted, D- and OH-are cis to one another.
Stereochemistry of the product
As we know that when we do hydroboration reaction borane group will add on the same side of the double bond of alkene i.e. cis product will form. Therefore, we can say that the stereochemistry of hydroboration- oxidation reaction is syn- addition (addition of deuterium and hydroxide on the same side of the double bond).
Product of the reaction
In this reaction, deuterated borane will form a complex with THF (tetrahydrofuran) because it is an explosive gas and will act as an electrophile, and a double bond of reactant 1- methylcyclopentene will act as a nucleophile and hydroboration reaction will take place i.e. deuterium ion will add on most substituted carbon. Then in the presence of a reagent oxidation reaction will take place. Hydroxide ion will add on less substituted carbon and with deuterium ion, it will form cis- product.
Hence, the product of the reaction is:
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