The alkene shown undergoes (i) $BH X_{3}$ in THF, then (ii) $H X_{2} O X_{2}$ , $NaOH$ . Which structure is the major product? (Relative configuration is what matters; one enantiomer of the racemate is drawn.)

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The alkene is 1-methylcyclohexene. Boron adds to the less substituted carbon and hydrogen to the carbon bearing the methyl, both from the same face (syn addition); oxidation then replaces boron by OH with retention. H on C-1 and OH on C-2 are syn, so the methyl and OH are trans: trans-2-methylcyclohexanol (racemic).

Practice Organic Reaction Mechanisms II: Electrophilic and Radical Reactions More on Markovnikov and anti-Markovnikov products of drawn alkenes

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The alkene shown undergoes (i) BHX3​ in THF, then (ii) HX2​OX2​, NaOH. Which structure is the major product? (Relative configuration is what matters; one enantiomer of the racemate is drawn.)

Answer: D

More questions on Markovnikov and anti-Markovnikov products of drawn alkenes

The alkene shown undergoes (i) $BH X_{3}$ in THF, then (ii) $H X_{2} O X_{2}$ , $NaOH$ . Which structure is the major product? (Relative configuration is what matters; one enantiomer of the racemate is drawn.)