Chapter 11: Ethers, Epoxides, and Sulfides
Table of contents of main topics:
Nomenclature of ethers
Select the longest continuous carbon chain that has OR as a substituent and number from the carbon closest to the OR group (OH has priority over OR).
Name the ether substituent (OR) with a number identifying carbon it is attached to followed by ...oxy ether
Identify the two R groups attached to the oxygen
Arrange R groups in alphabetical order and end the name with "ether"
If two of the same R groups are attached, then use prefix di
Preparation of Ethers
Williamson Ether Synthesis
Williamson ether synthesis is a reaction that converts alcohols into ethers (C-O-C). In the first step, alcohol is deprotonated using a strong base such as NaH. The alkoxide ion that is created is a strong nucleophile and can attack primary alkyl halides and tosylates in an SN2 reaction. The O- attacks the carbon the leaving group is attached to and the leaving group leaves.
Note: If the alkyl halide or tosylate is not primary, E2 will happen instead of SN2.
Acid Catalyzed Dehydration of Alcohols
2 alcohols can come together to form an ether with H2SO4 and heat.