Ch. 12 - Alcohols, Ethers, Epoxides and ThiolsSee 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

Ethers are almost completely unreactive to reactions. They can only undergo one useful reaction – they can break apart in the presence of strong acid. 

Concept #1: How to predict the products of Ether Cleavage. 

Example #1: Predict the product of the following reaction.  

Additional Problems
Which of these ethers is least likely to undergo significant cleavage by hot aqueous H2SO4?
Predict the product for the following reaction and determine if the product is given in the answer options below. If the answer is given, select the answer. Write "none" if the answer is not given.
What compounds would you expect to be formed when the following ether is refluxed with excess comcentrated hydrobromic acid?
What are the expected products from the reaction shown?
DRAW THE MOLECULAR STRUCTURE OF THE FOLLOWING REACTION PRODUCT(S). Major organic product (after workup) from the reaction of trans-3,4-dimethyloxacyclopentane (Lewis/Kekule structure at right below) with excess concentrated HBr.
Provide the major organic product(s) of the following.   
Draw the structural formulas for the products of the reaction shown below.
Draw the conjugate base for the following acid. Remember to include charges and non-bonding electrons where necessary CH3NH2
Complete the following reaction.
Draw structural formulas for the products of the reaction shown below. You do not have to consider stereochemistry. Assume equimolar amounts of the reagents. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the Separate multiple products using the - sign from the drop-down menu.
Predict the product(s) for the following reaction.  
Benzyl ethyl ether reacts with concentrated aqueous HI to form two initial organic products (A and B). Further reaction of product B with HI produces organic product C. Draw the structures of these three products.
Draw structural formulas for the products of the reaction shown below. • You do not have to consider stereochemistry. • Assume equimolar amounts of the reagents. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu.
Which one of the following statements about Reaction 4 is correct? a. The major organic product(s) arise via the SN1 pathway b. The major organic product(s) arise via the SN2 pathway