Organic Chemistry Chapter 18: Ethers, Thiols, and Epoxides

Vocabulary and concept flashcards covering ether structures, nomenclature, cleavage mechanisms, and epoxide synthesis based on the Chapter 18 lecture notes.

Tetrahydrofuran

A cyclic ether commonly used as a solvent, often abbreviated as THF.

12-crown-4

A specific crown ether containing four oxygen atoms in a twelve-membered ring.

3-methyl-1-butanethiol

A thiol compound consisting of a four-carbon chain with a methyl group at the third position and a sulfhydryl group at the first position.

m-chloroanisole

Also known as m-chloromethoxybenzene or (m-chlorophenyl) methyl ether.

1-ethoxy-2,2-dimethylpropane

A compound also referred to as ethyl neopentyl ether.

Diphenyl ether

A diaryl ether that is inert to cleavage by $HI$ or $HBr$ because the generation of an aryl cation is an $SN1$ process that is energetically unfavorable.

Acidic ether cleavage

Typical nucleophilic substitution reactions that take place by either an $SN1$ or $SN2$ pathway.

Acetals

A special class of ethers which have two ether linkages at a single carbon.

Tetrahydropyranyl ethers

Acetals that are easily cleaved with mild aqueous acids at room temperature to yield alcohols.

Resonance-stabilized carbocation

An intermediate in the $SN1$ cleavage of tetrahydropyranyl ethers that is stabilized by adjacent oxygen lone pairs.

1,2-epoxypropane

A three-membered cyclic ether that reacts with sodium ethoxide to produce 1-ethoxy-2-propanol as the major product.

m-chloroperoxybenzoic acid

A reagent used on a laboratory scale to convert an alkene into an epoxide in one step.

Halohydrins

Intermediate compounds converted by treatment with base into epoxides via an intramolecular Williamson ether synthesis.

Alkoxymercuration-demercuration

A two-step reaction sequence using $Hg(O_2CCF_3)_2$ and an alcohol followed by $NaBH_4$ to synthesize ethers from alkenes.

1,4-dioxane

A cyclic diether that can be synthesized starting from 1,2-dibromoethane.

o-mercaptotoluene

A toluene derivative containing a thiol (-SH) group at the ortho position.

Claisen Rearrangement

The process by which compounds like 2-butenyl phenyl ether or 1-propenyl 2-propenyl ether undergo rearrangement upon heating.