Ch. 12 - Alcohols, Ethers, Epoxides and ThiolsWorksheetSee 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

Same reagents as acid-catalyzed hydration, except with alcohol as the nucleophile instead of water.

Concept #1: The Mechanism of Alkoxylation. 

Additional Problems
Predict the following synthesis:   
A. Draw the mechanism of the following transformation. Show all steps of the reaction including curved arrows, lone pairs of electrons, formal charges, inorganic products and intermediates. Only only one of the stereoisomeric products needs to be drawn for the mechanism.     B. This reaction proceeds through what type of mechanism?     C. Would the resulting reaction mixture be optically active or optically inactive?     D. What is the relationship between the products?    
Predict the neutral organic product of the following reaction. Include hydrogen atoms in your structure. 
Predict the organic product(s) for the following reaction. Be sure to indicate stereochemistry when appropriate. If stereoisomers are produced draw one and label the relationship between the stereoisomers. (enantiomers, diastereomers, etc.).
Predict the organic product(s) for the following reaction. Be sure to indicate stereochemistry when appropriate. If stereoisomers are produced draw one and state the relationship between the otherstereoisomer formed. (enantiomers, diastereomers, etc.).
Treatment of alcohol A with HCl (catalyst) in CH3OH as the solvent produces 3 different polyenes B, C, and D that have the same molecular formula (MF= C9H16O) and contain only trans alkenes. Predict the structures of B, C and D.b.  Which one of the alkenes B, C, D will be favored under thermodynamic or kinetic control? Explain your answer in 1-2- sentences.