Organic Chemistry

1. Are borneol and isoborneol considered diastereomers or enantiomers?  Why?

1. Why can one mole of borohydride reduce four moles of camphor (consider structure)?  

1. Why is the endo or exo attack of the hydride on the camphor the preferred approach?

1. What is being reduced and what is being oxidized in the reduction of camphor to isoborneol?  How can you tell?

1. Why did the isoborneol precipitate out of solution when the "ice water" was added?

1. What was the one main purpose for dissolving the precipitated isoborneol in methylene chloride, adding drying agent, and then distilling off the methylene chloride?

1. See Pavia, Part C, NMR Determination to answer the following questions.
   1. At which chemical shift does the hydrogen on the carbon bearing the hydroxyl group appear in the proton NMR spectra of: 
      1. Borneol 1 point
      2. Isoborneol 1 point
   2. Given the 1H-NMR spectral data resulting from a student's Reduction of Camphor experiment (below), calculate what percent of the student's product was Borneol and what percent was Isoborneol.  Show all work.  

Shift (ppm)

Integration

4.0

1.05

3.6

6.24