Question

1. We decided to use 5.2 molar equivalents based on our past experience performing this type of reduction. What is the theoretical absolute minimum number of molar equivalents one could use in a sodium borohydride reduction of a ketone like camphor? (Think about the structure of sodium borohydride).

2. Consider the reducing agent LiAlH4 as an alternative reagent, which is typically used in THF, followed by careful aqueous workup. If LiAlH4 would be used, what would the consequence be of using an alcoholic solvent (like in this weeks experiment) instead of an inert solvent like THF? Draw a mechanism describing what might happen. You might want to review the LiAlH4 reagent in your organic book / Chem233 notes.

3. When menthone is reduced by NaBH4, two products are formed (a major one and a minor one). Predict the structure of the two molecules. What is the stereochemical relationship between the two molecules? (enantiomers, diastereomers, etc.)