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Chapter 11 OChem

Ethers, Epoxides, and Sulfides

What is an ether? an atom of oxygen bonded to two carbon atoms.
dimethyl ether -two sp3 hybridized oxygens
Alkoxy group An -OR group, where R is an alkyl group
ring sizes 3-6 -irane, -etane, -olane, and -ane
Heterocycle a cyclic compound whose ring contains more than one kind of atom.
Physical Ether Properties -polar, weak dipole-dipole interactions in liquid state, boiling points are low, insoluble in water
Preparation of Ethers Williamson Ether Synthesis, Acid-Catalyzed Dehydration of Alcohols, Acid-Catalyzed Addition of Alcohols to Alkenes
Williamson ether synthesis a general method for the synthesis of diakyl ethers by an SN2 reaction between a haloalkane and an alkoxide ion.
Ether Reactions do not react with oxidizing agents such as potassium dichromate or potassium permanganante; stable towards stronger bases
What do cleavage of dialkyl ethers require? strong acid and good nucleophile
What types of ethers are susceptible to cleavage by acid under mild conditions? tertiary, allylic, and benzylic
ether safety low boiling point; highly flammable; explosive
hydroperoxide a compound containing an -OOH group
protecting group -easily added to sensitive functional group -resistant to reagents used to transform the unprotected functional group - easily removed to regenerate the original functional group
silyl ethers unaffected by most oxidizing and reducing agents and are stable to most nonaqueous acids and bases
epoxides a cyclic ether in which oxygen is one atom of a three-membered ring.
Created by: savepeople