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

There are 4 major methods to create ethers. Most of these should look familiar in some way since they are variations of reactions we have used before. 

Williamson Ether Synthesis

The name given for the SN2 substitution of an oxide with an alkyl halide.

  • Only works with 0°, 1° alkyl halides since 2° and 3° alkyl halides will favor E2

Concept #1: The Mechanism of Williamson Ether Synthesis. 

Additional Problems
Which compound will be the organic product after the following two steps?  
Draw the ether of molecular formula C 5H10O from BrCH2CH2CH2CH2CH2Br + NaOH in CH3OH.
Predict the product of the following reaction.
Predict the product. 
Predict the product:
Predict the organic product(s) of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product, if stereoisomers are produced in the reaction be sure to indicate the relationship between them. Draw all answers in skeletal form.
Use retrosynthesis to suggest an efficient pathway to ether (C) via the use of Williamson Ether Synthesis
Which reaction would produce phenyl propyl ether?
Predict the product of the following reactions showing stereochemistry when applicable. If there is no reaction, just write “no reaction” in the box.
Provide the major organic product of the reaction below.  
Provide the structure of the major organic product of the following reaction. 
Provide the structure of the major organic product in the reaction below.  
Provide the major organic product of the following. 
Predict the product for the following reaction. 
Identify the product of the following reaction: 
Predict the product for the following
Provide the structure of the major organic product in the reaction below.  
For the reaction below: Draw the major organic product in the sketch pad below. If the reaction produces a racemic mixture, draw both stereoisomers.
Draw the major organic product of the reaction below.  
Which of the following mechanistic steps is the most likely route for the formation of the cyclic either shown? 
Provide the structure of the major organic product in the reaction below.