Ch. 6 - Thermodynamics and KineticsSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Carbocation Intermediate Rearrangements

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Solution: When compound shown below is exposed to an acid, a molecule ...

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.