Alcohols, Phenols and Ethers - Vocabulary Flashcards

Vocabulary flashcards covering key concepts, definitions, and reactions related to alcohols, phenols, and ethers from the lecture notes.

Alcohol

Compounds containing a hydroxyl (-OH) group attached to an alkyl (or aryl) group.

Primary alcohol (1°-alkanol)

R-CH2-OH; OH on a carbon attached to one other carbon (mostly primary).

Secondary alcohol (2°-alkanol)

R-CH(OH)-R'; OH on a carbon attached to two carbon atoms.

Tertiary alcohol (3°-alkanol)

R-C(OH)(R')(R''); OH on a carbon bearing three carbon substituents.

Allylic alcohol

An alcohol where the hydroxyl-bearing carbon is adjacent to a C=C double bond.

Vinylic alcohol

An alcohol in which the OH is attached to a vinyl (sp2) carbon.

Benzylic alcohol

An alcohol where the OH is on a benzylic carbon attached to a benzene ring.

Phenol

A hydroxybenzene: hydroxyl group directly attached to an aromatic benzene ring.

Ortho/Meta/Para (on benzene)

Relative positions of substituents on a benzene ring: ortho (1,2-), meta (1,3-), para (1,4-).

Methanol

IUPAC name for CH3OH; also known as methyl alcohol (wood spirits).

Ethanol

IUPAC name for CH3CH2OH; also known as ethyl alcohol.

Propane-1-ol (Propan-1-ol)

CH3CH2CH2OH; primary alcohol.

Propane-2-ol (Propan-2-ol)

CH3CH(OH)CH3; secondary alcohol (isopropanol).

Prop-1-en-ol (Propenol)

CH2=CH-CH2OH; allylic alcohol (allyl alcohol).

Catechol

1,2-dihydroxybenzene.

Resorcinol

1,3-dihydroxybenzene.

Hydroquinone

1,4-dihydroxybenzene.

IUPAC name: Methanol (methyl alcohol)

Methanol; CH3OH; common IUPAC name is methanol.

IUPAC name: Ethanol (ethyl alcohol)

Ethanol; CH3CH2OH; common IUPAC name is ethanol.

Ethoxyethane

IUPAC name for diethyl ether; CH3CH2-O-CH2CH3.

Anisole

Methoxybenzene; C6H5-O-CH3.

Ether

An organic compound with the functional group R-O-R' (oxygens linking two carbon groups).

Diethyl ether

Common ether; IUPAC name: Ethoxyethane; CH3CH2-O-CH2CH3.

Williamson synthesis

Preparation of ethers by reaction of an alkoxide with an alkyl halide: R-O− + R′-X → R-O-R′.

Ether formation from haloalkanes (alternative method)

Haloalkanes react with Ag2O (or NaO−) to give ethers under heat.

Dehydration to form ethers (from alcohols)

Two alcohol molecules condense to form an ether and water under acid catalysis.

Catalytic dehydration of alcohols to ethers

Primary alcohols may form ethers over red-hot alumina at high temperature.

Hydration of alkenes to alcohols

Addition of water to alkenes in acid to form alcohols (Markovnikov orientation typically).

Alcohols from aldehydes/ketones (formation of alcohols)

Aldehydes/ketones reduced (e.g., LiAlH4 or NaBH4) to give primary/secondary alcohols.

Reduction of carboxylic acids to alcohols

Carboxylic acids reduced with LiAlH4 to give primary alcohols.

Reduction of esters to alcohols

Esters reduced (e.g., LiAlH4) to primary alcohols.

Alcohols from Grignard reagents

Aldehydes/ketones react with RMgX to give secondary/tertiary alcohols after acidic workup.

Hydrolysis of esters to alcohols

Esters hydrolyze to alcohols under acidic or basic conditions to yield alcohols.

Alcohols from haloalkanes (KOH)

Primary haloalkanes → primary alcohols with aqueous KOH; secondary haloalkanes → secondary alcohols; tertiary halos → elimination to alkenes.

Amines to alcohols via nitrous acid

Primary amines react with HNO2 to yield primary alcohols after hydrolysis.

Solubility of alcohols

Lower alcohols dissolve in water due to hydrogen bonding; solubility decreases with increasing carbon chain length.

Acidity: Phenols vs alcohols

Phenols are more acidic than ordinary alcohols due to resonance stabilization of the phenoxide ion.

Phenoxide

The conjugate base of phenol (ArO−) formed after deprotonation by base.

Dow/Raschig process for phenol

Chlorobenzene treated with NaOH at high temperature/pressure with Cu2+ to form sodium phenoxide, hydrolyzed to phenol.

Cumene process for phenol

Cumene reacts with O2 to form cumene hydroperoxide, hydrolyzed to phenol and acetone.

Benzenesulfonic acid to phenol

Benzenesulfonic acid fused with NaOH forms sodium phenoxide, which hydrolyzes to phenol.

Diazonium salt to phenol

Benzene diazonium salt treated with warm water to form phenol.

Grignard to phenol via oxygen

Phenylmagnesium bromide reacts with O2 to form phenoxide, hydrolysis yields phenol.

Fries rearrangement (phenols)

Acyl migration from phenyl ester to ortho/para positions on the ring under Lewis acid to form o-/p-hydroxy ketones.

Kolbe reaction (carboxylation of phenoxide)

Sodium phenoxide reacts with CO2 to give salicylic acid after hydrolysis.

Reimer–Tiemann reaction

Phenol reacts with chloroform in base to give salicylaldehyde, which hydrolyzes to salicylic acid.

Diazo-coupling with phenol

Diazobenzene couples with phenol in base to give azo dyes (e.g., orange II-type).

Hydrogenation of phenol

Phenol hydrogenated with H2 over Ni catalyst to give cyclohexanol.

Oxidation of phenol to benzoquinone

Phenol oxidized (often with Cr catalyst and O2) to benzoquinone.

Bromination of phenol

Phenol bromination occurs at ortho/para positions; excess Br2 with water can give 2,4,6-tribromophenol.

Nitration of phenol

Phenol reacts with dilute HNO3 to give ortho- and para-nitrophenol; concentrated acids give polynitrated products.

Sulphonation of phenol

Phenol reacts with concentrated H2SO4 to form ortho- and para-hydroxybenzenesulfonic acids.

Friedel–Crafts alkylation of anisole

Anisole undergoes Friedel–Crafts alkylation with alkyl chlorides in AlCl3 to give ortho/para methyl anisole.

Friedel–Crafts acylation of anisole

Anisole undergoes Friedel–Crafts acylation with acetyl chloride in AlCl3 to give 2-/4-methoxyacetophenone.

Aryloxy ethers (anisole formation)

Sodium phenoxide reacts with methyl bromide to form anisole (methoxybenzene).

Aryl ethers from diazomethane

Diazomethane can react to form ether derivatives with alcohols under acidic conditions.

Dichloro ethers

Aliphatic ethers react with chlorine to form dichloro ethers.

Solvent and anesthetic uses of diethyl ether

Diethyl ether used as industrial solvent, in surgery as anesthetic, and as refrigerant.

Inertness of ethers

Ethers are relatively inert due to lack of highly reactive sites; cleavage occurs mainly with strong acids or bases.

Ethers vs acids/bases statement

Ethers are cleaved by strong acids; they are not readily cleaved by bases under normal conditions.