ALCOHOLS & PHENOLS (ORG CHEM)

Alcohols

Compounds that possess a hydroxyl group (OH) and are characterized by names ending in ol

simple alcohols

are about as acidic as water

alkyl groups

make an alcohol a weaker acid

phenols

• pKa ~10

• much more acidic than alcohols

• react with NaOH solutions, forming salts that are soluble in dilute aqueous solution

Alcohols

• pKa ~ 16

• do not react with NaOH

• higher boiling points than alkylhalides and alkanes

ethane

boiling point = -89℃

chloroethane

boiling point: 12℃

ethanol

boiling point: 78℃

alcohol solubility

in water increases with increase in chain length up to 8 carbons.

insoluble in water

alcohols with >8C

a-carbon

carbon attached to the functional group

primary alcohol

secondary alcohol

tertiary alcohol

antibacterial potency

_____ of primary alcohols increases with increasing molecular weight , up to an alkyl chain length of eight carbon atoms (octanol)

aldehydes

reduction of ____ gives primary alcohols

ketones

reduction of ______ gives secondary alcohols

SOCl₂
PBr₃

primary and secondary alcohols react with ____ and ____

alkyl chlorides

product of the substitution reaction of primary and secondary alcohols with SOCl₂

alkyl bromides

product of the substitution reaction of primary and secondary alcohols with PBr₃

HCl or HBr

tertiary alcohols react with ____ or ____

oxidation

addition of OXYGEN

removal of HYDROGEN

reduction

removal of OXYGEN

addition of HYDROGEN

pyridinium chlorochromate (PCC)

reagent used in the reaction:
primary alcohol —(oxidation)→ aldehyde

Dess-Martin periodinane (DMP)

reagent used in the reaction:
secondary alcohol —(oxidation)→ ketone

esters

Alcohols react with carboxylic acids to give ____, in the presence of an acid

saponification

• base-hydrolysis reaction of ESTER

• ESTER + NaOH → carboxylic acid + alcohol

chloramphenicol

• an antibiotic isolated from the Stremptomyces venezuelae bacterium

• potent against typhoid fever

geraniol

• isolated from roses and geraniums

• used in perfumes

cholesterol

• plays a vital role in the biosynthesis of many steroids