Question

Draw all the structures of the isomeric alcohols (C5H12O) that can be prepared by reduction of...

  1. Draw all the structures of the isomeric alcohols (C5H12O) that can be prepared by reduction of a ketone using sodium borohydride?

  2. Circle all the structures from the previous question that present diastereotopic hydrogens, and box any structures that present enantiotopic hydrogens.

  3. Take the only circled achiral structure from the first question and draw two wedge and dash structures that clearly demonstrate that the diastereotopic hydrogens are not equivalent using deuterium to substitute for hydrogen. Label any stereogenic centers either R or S.

  4. Take the only boxed structure from the first question and draw two wedge and dash structures that clearly demonstrate a pair of enantiotopic hydrogens that are in equivalent environments using deuterium to substitute for hydrogen. Label any stereogenic center(s) either R or S.

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