Alcohols: Reactions

For each of the reactions on the left, predict the major organic product. Pay particular attention to the regiochemistry and stereochemistry of the reaction.
Click the mouse on the reactant molecule to view the answer;

click on the reagent to review the mechanism and regiochemistry of the reaction.

BH₃, followed by oxidative work-up, converts an alkene into an anti-Markovnikov alcohol and the addition of H and OH is syn.

LiAlH₄ reduction of an ester converts the carbonyl into a primary alcohol; the alcohol portion of the ester is "lost" in the reaction.

OsO₄ converts an alkene into a 1,2-diol. The addition is cis-, but in this case there is free rotation around the single bond so there is no stereochemistry.

BH₄^- reduces a ketone to the corresponding secondary alcohol.

BH₃, followed by oxidative work-up, converts an alkene into an anti-Markovnikov alcohol and the addition of H and OH is syn.

LiAlH₄ reduction of an ester converts the carbonyl into a primary alcohol; the alcohol portion of the ester is "lost" in the reaction.

OsO₄ converts an alkene into a cis-1,2-diol.

BH₄^- reduces a ketone to the corresponding secondary alcohol.