Ethers, Sulfides, Epoxides, and Sulfur Functional Groups

Vocabulary

acidic cleavage

breaking of a covalent bond using an acid

alcohol

organic molecule with a hydroxyl group attached to an sp3-hybridized carbon

alkanethiolate

thiol that has had the hydrogen of the thiol (SH) removed

alkoxymercuration-demercuration

use of mercury acetate to form ethers (alkoxy groups)

autoxidation

spontaneous oxidation at room temperature in the presence of oxygen

crown ether

cyclic compound consisting of repeating ${-}{\rm {CH}}_2{\rm {CH}}_2{\rm {O}}{-}$ units

dehydration

removal of water from a compound

disulfide

organic molecule containing two sulfur atoms that are each bound to either a hydrogen, alkyl, or aryl group through ${\rm {C{-}S}}$ bonds

enantioselective reaction

chemical reaction in which one enantiomer of a chiral product is preferentially formed

epoxidation

chemical reaction that creates an oxirane ring (three-membered ether)

epoxide

compound that contains a cyclic ether made of two carbons and an oxygen

ether

organic molecule containing an oxygen atom bound by two alkyl or aryl groups through ${\rm {C{-}O}}$ bonds

halohydrin

organic molecule with a halogen and a hydroxyl group on adjacent carbons

nucleophile

molecule or ion rich in electrons that donates a pair of electrons to form a covalent bond

oxirane

cyclic three-membered ether ring, C2H4O

peroxy acid

acid that contains the COOOH, or CO3H, group

ring opening

reaction where a ${\rm {C{-}C}}$ bond is broken in a carbon ring

Sharpless epoxidation

enantioselective method of epoxidation that can yield not only a syn product but only one of the two possible syn isomers using diethyl tartrate (DET)

substituent

atom or group of atoms (functional group) that replaces a ${\rm {C{-}H}}$ bond in an organic compound

substitution

chemical reaction where one functional group replaces another functional group

sulfide

organic molecule containing a sulfur bonded to two alkyl or aryl groups through ${\rm {C{-}S}}$ bonds

sulfone

organic molecule containing a sulfur double bonded twice to oxygen atoms and single bonded twice to alkyl or aryl groups through ${\rm {C{-}S}}$ bonds

sulfoxide

organic molecule containing a sulfur double bonded to an oxygen atom and single bonded twice to alkyl or aryl groups through ${\rm {C{-}S}}$ bonds

thiol

organic compound that is derived from hydrogen sulfide (H2S). It contains an alkyl or aryl group covalently linked to a sulfhydryl group, ${-}{\rm {SH}}$, through ${\rm {C{-}S}}$ bonds, with $\rm R{-}\rm {SH}$ stoichiometry.

Williamson synthesis

organic reaction used to convert an alcohol and an alkyl halide to an ether using a base, such as sodium hydroxide (NaOH)