carboxylic acids and esters

form hydrogen bonds - high mps and bps compared to similar sized alkanes

COOH group very soluble in water due to H bonding but the hydrocarbon chain is non - polar so doesnt dissolve in water short chain carboxylic acids dissolve easily in water - short hydrocarbon chain longer chain carboxylic acid is less soluble - longer hydrocarbon chain

acids as they donate protons weak acids so equilibrium is to the left react with alcohols to form esters

first part - chain attached to O - …thyl second part - chain attached to double bond O - propanoic acid —- propanoate

carboxylic acid + alcohol condensation reaction and conc H2So4 catalyst reversible reaction water is by product

acid catalysed hydrolysis -hard to get high yield of carboxylic acid and alcohol base catalysed hydrolysis -carboxylic acid reacts with NaOH and forms a salt of the acid -increases the yield and shifts the position of the equilibrium to the right -not appropriate if salt is not desired products

triesters + NaOH —–heat—-> 3sodium carboxylate/ soap + glycerol

triesters + CH3OH —–heat—-> 3 methyl esters/ biodiesel + glycerol

acid anhydrides are unsymmetrical so there are two possible products depending on the carbonyl group the nucleophile attacks

Cheaper Less corrosive Don’t react with water - less vulnerable to hydrolysis Safer as product is carboxylic acid and acyl chlorides produce Hcl