1) Draw the mechanism of the reaction. You may write "H " instead of the full structure of camphorsulfonic acid. 2) There are two possible isomers of the product acetal that could conceivably be formed. Draw them, and make sure you use the chair conformation of the 6-membered ring. 3) Which of those two conformations is the most favorable. Explain your answer. 4) There is only one major product of this reaction - based on your answer to Q3, identify it and explain your reasoning.5) The 1H NMR spectrum has peaks (marked with "x") for a minor byproduct - what might that be? 6) Why did we use solid camphorsulfonic acid rather than aqueous H2SO4?7) Identify the peak in the 1H NMR spectrum corresponding to the CH3 group, explain what coupling pattern it has and why it has that pattern.
8) The 1H NMR peaks corresponding to Ha and Hb in your product (shown on the right) appear at 4.17 and 3.50 ppm respectively. Describe the observed coupling pattern for each peak, and explain why the two peaks show different coupling patterns.