Organic Chemistry Chapter 10

acid derivatives

compounds that are related to carboxylic acids but have other electron-withdrawing groups in place of the -OH group of the acid. Three examples are acid chlorides, esters, and amides.

alcohol

a compound in which a hydrogen atom of a hydrocarbon has been replaced by a hydroxyl group -OH. Alcohols are classified as primary, secondary, or tertiary depending on whether the hydroxyl group is bonded to a primary, secondary, or tertiary carbon atom.

aldehyde

a carbonyl compound with one alkyl group and one hydrogen on the carbonyl group

formaldehyde

has two hydrogens on the carbonyl group

alkoxide ion

the anion (R-O^-) formed by deprotonation of an alcohol.

azeotrope

a mixture of two or more liquids that distills at a constant temperature and gives a distillate of definite composition. For example, a mixture of 96% ethanol and 5% water has a lower boiling point than pure ethanol or pure water.

carbinol carbon atom

in an alcohol, the carbon atom bonded to the hydroxyl group

denatured alcohol

a form of ethanol containing toxic impurities, making it unfit for drinking.

diol

a compound with two alcohol -OH groups.

disulfide

the oxidized dimer of a thiol, R-S-S-R

epoxides

(oxiranes) compounds containing oxygen in a three-membered ring

ester

an acid derivative in which the hydroxyl group of the carboxylic acid is replaced by an alkocy (-OR') group

glycol

synonymous with diol

grain alcohol

ethanol, ethyl alcohol

absolute alcohol

100% ethanol

Grignard reagent

an organomagnesium halide, written in the form R-Mg-X. The actual reagent is more complicated ins structure, usually dimer or trimer complexed with several molecules of ether.

hydride reagent

a compound of hydrogen with a less-electronegative element, so the hydrogen can be donated with its pair of electrons. Simple hydrides like NaH and LiH tend to be more basic than nucleophilic, often reacting with H+ to give H2 gas. The complex hydrides Na

hydrophilic

("water loving") attracted to water, water-soluble

hydrophobic

("water hating") repelled by water, water-insoluble

hydroxy group

(hydroxyl group) the -OH group, as in an alcohol

ketone

a carbonyl compound with two alkyl groups bonded to the carbonyl group

lithium dialkylcuprate

(Gilman reagent) an organometallic reagent used to couple with an alkyl halide

mercaptan

(thiol) the sulfur analogue of an alcohol, R-SH.

miscible

mutually soluble in any proportions

organolithium reagent

an organometallic reagent of the form R-Li

organometallic compounds

(organometallic reagents) compounds containing metal atoms directly bonded to carbon

phenol

a compound with a hydroxyl group bonded directly to an aromatic ring

Raney nickel

a finely divided nickel/aluminum alloy that has been treated with NaOH to dissolve out most of the aluminum. Used as a catalyst for the hydrogenation of ketones and aldehydes to alcohols

rubbing alcohol

propan-2-ol, isopropyl alcohol

skunk smell

thiolds

sulfuric acid

a strongly acidic compound of formula R-SO3H, formed by vigorous oxidation of a thiol.

thiol

(mercaptan) the sulfur analogue of an alcohol, R-SH

thiolate ion

the R-S^- anion, formed by deprotonation of a thiol

wood alcohol

methanol, methyl alcohol