Organic Chemistry by Brown, Iverson, Anslyn, Foote | Mayya's Study Guide | Chapter 11

Chapter 11: Ethers, Epoxides, and Sulfides

Table of contents of main topics:

• Nomenclature of ethers

• Preparation of ethers

• Reactions of ethers

• Silyl Ethers as protecting groups

• Synthesis of epoxides

• Reactions of epoxides

• Sulfides

• Summary of the chapter reactions

Nomenclature of ethers

IUPAC Name

1. 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).

2. Name the ether substituent (OR) with a number identifying carbon it is attached to followed by ...oxy ether

Common Name:

1. Identify the two R groups attached to the oxygen

2. Arrange R groups in alphabetical order and end the name with "ether"

3. 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.

Williamson Ether Synthesis

How to predict the reactants of Williamson Ether Synthesis when product is given

Acid Catalyzed Dehydration of Alcohols

2 alcohols can come together to form an ether with H2SO4 and heat.

Acid Catalyzed Dehydration of Alcohols

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