Problem: When compound shown below is exposed to an acid, a molecule of water is eliminated, and a structural rearrangement ensues. The final product is a ketone with a molecular formula C18H18O. However, despite the fact that there are two –OH groups in the starting material, only one ketone is produced, with greater than 99% selectivity. Draw (a) the structure of that ketone and (b) the detailed mechanism that explains its formation. Then (c) provide a brief explanation why no other products are formed. Show all charges and intermediates, and use curved arrows to indicate the flow of electrons. Do not draw transition states.

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Problem Details

When compound shown below is exposed to an acid, a molecule of water is eliminated, and a structural rearrangement ensues. The final product is a ketone with a molecular formula C18H18O. However, despite the fact that there are two –OH groups in the starting material, only one ketone is produced, with greater than 99% selectivity. Draw (a) the structure of that ketone and (b) the detailed mechanism that explains its formation. Then (c) provide a brief explanation why no other products are formed. Show all charges and intermediates, and use curved arrows to indicate the flow of electrons. Do not draw transition states.

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