chapter 16

Carboxylic acids

Class of c=o compounds, key for protiens

Acrylic diacarboxylic acids

Carboxylic acids that contain two acid groups

Aromatic Carboxylic acid nomenclature

Named as derivatives of benzene (-benzoic acid)

CHO-OH/ formic acid

Methanoic acid

CH3(CH2)2COOH/ butyric acid

Butanoic acid

CH3(CH2)10COOH/ lauric acid

dodecanoic acid

CH3(CH2)14COOH/ palmtic acid

hexandecanoic acid

CH3(CH2)16COOH/ stearic acid

Octadecanoic acid

Physical compounds of Carboxylic acids

Polar compunds: highly influence their physical compounds

higher BP than other organic compunds d/t polarity and strong hydrogen bonds b/w molecules

More soluble in water than alcohols, ketones, and aldehydes d/t water molecules

Carbon chains and solubility

As carbon chains increase, solubility decreases

Carbon chains 1-5 are VERY soluble in water

Carboxylic acids are…

More soluble and have a higher BP than alcohols, ketones, and aldehydes

Carboxylic acids form strong…

Hydrogen bonds, act as dimers

Boiling points of Carboxylic acids

Polar Carboxylic groups allow Carboxylic acids to form multiple hydrogen bonds w/ other Carboxylic acids, this is why it has higher BP than other friends of similar mm

Acidity

Weak acids, dissociate to produce carboxylate and hydronium

Acid-base rxns

React w/ string bases to form carboxylate salts

Esters

Synthesized form the rxn of Carboxylic acids and alcohols, found in fats/oils, good odors like fruit

Esterification

Rxn of Carboxylic acids and alcohols in the presence of an acid catalyst to produce ester

Physical properties of esters

C=o group acts as hydrogen bond acceptor, more water soluble than corresponding alkanes, BP lower d/t no intermolecular forces

ethyl butanoate

Pineapple

Methyl salicylate

Wintergreen

Ethyl methanoate

Raspberry

Isopentyl ethanoate

Banana

Methyl butanoate

Apple

Plenty's butanoate

Pear/apricot

O toy butanoate

Orange

Acid hydrolysis

Ester rxs w/ water to produce Carboxylic acid and an alcohol

Base hydrolysis

Saponification/soap making, produces acid salt and alcohol, produces acid salt bc of basic conditions