Carboxylic Acids and Esters

carboxylic acid

-carboxyl fuc grp

-contains carbonyl and hydroxyl grp

-naming; carbon w/ carboxyl grp is carbon 1

-carboxyl always at the end

solubility

-can dissolve in polar solvent like water

-can hydrogen bonds with water molecules

-hydrocarbon part is non polar so bigger it is the less soluble carboxylic acid becomes

carboxylic acid chemical properties

-react w/ carbonates

-weak acid; dissociate partially to H+ ion and carboxylate ion

-equilibrium lies to left due to poor dissociation

carboxylic acid reaction with carbonate, bases, alkalis, metal oxides, metal

-carbonate: form salt, CO₂, water

-bases, alkalis, metal oxides: salt and water

-metal: salt and H gas

2CH₃COOH + Na₂CO₃ →

2CH₃COOH + Na₂CO₃ → 2CH₃COONa + H₂O + CO₂

CH₃COOH + NaHCO₃ →

CH₃COOH + NaHCO₃ → CH₃COONa + H₂O + CO₂

CH₃COOH + NaOH →

CH₃COOH + NaOH → CH₃COONa + H₂O

2CH₃COOH + MgO →

2CH₃COOH + MgO → (CH₃COO)₂Mg + H₂O

2CH₃COOH + Mg →

2CH₃COOH + Mg → (CH₃COO)₂Mg + H₂

acyl clhoride

-func grp: -COCl

-suffix -oyl chloride

-made by reacting carboxylic acid with thionyl chloride (SOCl₂)

-CH₃COOH + SOCl₂ → CH₃COCl + SO₂ + HCl

what do acyl chlorides react with

-water

-ammonia

-alcohol

-primary amine

-Cl is always substituted

acyl chloride reaction w/ water

-produces carboxylic acid

-Cl sub for OH

-nucleophilic addition

-elimination reaction

-vigorous reaction; white misty fumes of HCl gas produced

acyl chloride reaction w/ ammonia

-produces amide

-Cl sub for NH₂

-nucleophilic addition

-elimination reaction

-vigorous reaction; white misty fumes of HCl gas produced

acyl chloride reaction w/ alcohol

-produces ester

-Cl sub for OCH₃

-nucleophilic addition

-elimination reaction

-vigorous reaction; white misty fumes of HCl gas produced

acyl chloride reaction w/ primary amine

-produces N-substituted amide

-Cl sub for NHCH₃

-nucleophilic addition

-elimination reaction

-vigorous reaction; white misty fumes of HCl gas produced

acid anhydride

-molecule made from 2 carboxylic acids that are same

how to name acid anhydride

-suffix; replace acid with anhydride

-prefix; C chain length of 1 of the acid

ways to make ester

-acyl chloride reaction w/ alcohol

-acid anhydride reaction w/ alcohol

-acyl chloride reaction w/ phenol

-carboxylic acid reaction w/ alcohol

acid anhydride reaction w/ alcohol

-similar to acyl chloride but less vigorous reaction

-produce ester

acyl chloride reaction w/ phenol

-form ester

-Cl replaced by phenol w/ O

carboxylic acid reaction w/ alcohol

-w/ sulfuric acid catalyst

-produces ester and water

-OH from carboxylic acid and H from alcohol form water

acid anhydride reaction w/ alcohol

-forms ester and carboxylic acid

ester naming

-first bit named from alcohol

-ethanol → ethyl

-second bit named from carboxylic acid (part w/ O)

-propanoic acid → propanoate

name this

-ethyl,2,methyl,propanoate

ester hydrolysis

-can be sped up using acid/base hydrolysis

acid hydrolysis ester

-dilute acid (HCl/ H₂SO₄) used

-to split into carboxylic acid and alcohol

-conducted under reflux as products are volatile and may be lost

-addition of water shifts equilibrium to right so more product made

base hydrolysis ester

-dilute base (NaOH) used

-split into carboxylate ion and alcohol

-conducted under reflux