1-Methylcyclopentene can be converted into the given compound
by the use of which of the following reagents?
BH3 followed by
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This involves hydroboration-oxidation to achieve anti-Markovnikov addition of water. The key is tracking deuterium (D) placement.
The target compound has deuterium on the methyl group, meaning the boron must add to the less substituted carbon. Using BD3 provides the deuterium. Oxidation with HCOOH (formic acid) replaces the boron with H, giving the final structure where D is on the carbon originally bonded to boron.
The correct reagent sequence is: followed by HCOOH.
Final Answer: BD3 followed by HCOOH