Ch. 6 - Thermodynamics and KineticsWorksheetSee 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

Solution: 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.

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.