CARBOXYLIC ACIDS

Unit 4.8.3 a d Syllabus

a. give some examples of molecules that contain the carboxylic acid functional group b. explain the physical properties of carboxylic acids in relation to their boiling temperatures and solubility due to hydrogen bonding c. describe the preparation of carboxylic acids to include oxidation of alcohols and carbonyl compounds and the hydrolysis of nitriles d. describe and carry out, where appropriate, the reactions of carboxylic acids. This will be limited to: i. ii. iii. iv. reduction with lithium tetrahydridoaluminate (lithium aluminium hydride) in dry ether (ethoxyethane) neutralization to produce salts, eg to determine the amount of citric acid in fruit phosphorus(V) chloride (phosphorus pentachloride) reactions with alcohols in the presence of an acid catalyst, eg the preparation of ethyl ethanoate as a solvent or as pineapple flavouring.

Carboxylic acid structure

Formula -COOH

Oxygen atoms not joined together.

General formula when rest of structure is an alkyl group R-COOH.

Carboxyl group

NAMES OF CARBOXYLIC ACIDS

Do you know any names?

They are named by taking the name of the alkane with the same number of C atoms and replacing the -ane with an oic acid

Naming carboxylic acids

Alkanes CH4 methane CH3 -CH3 ethane CH3-CH2-CH3 propane. Carboxylic acids H-COOH methanoic acid CH3 -COOH ethanoic acid CH3-CH2-COOH propanoic acid

Naming more complex examples

Two carboxylic acid groups -dioic Carboxyl group can be attached to a benzene ring eg benzenecarboxylic acid.
COOH

ethanedioic acid COOH

benzene-1,4dicarboxylic acid

COOH

benzenecarboxylic acid (benzoic acid)

propanedioic acid

Naming practise.
Name these structures

Butanoic acid

Octanoic acid

Pentanedioic acid Benzene-1,2-dicarboxylic acid

Physical Properties
Even the simplest carboxylic acids are liquids at room temperature
Because of hydrogen bonding between the carboxylic acid groups they have relatively high boiling points Carboxylic acids with more than 8 carbon atoms in the chain are solids Benzoic acid is also a solid at room temp

Physical Properties
Carbon-oxygen bonds are polar.
The polar bonds make small carboxylic acids very soluble in water Because they can form hydrogen bonds with the water molecules Solubility decreases as carbon chain length increases

Longer chains have stronger intermolecular forces between them

If these intermolecular forces are stronger than the hydrogen bonds would be, the carboxylic acid wont dissolve

Preparation of Carboxylic acids

Prepared in the lab by oxidising primary alcohols or aldehydes
[oxidising agent is potassium dichromate(VI)]

Preparation of Carboxylic acids

Can also be made by hydrolysing nitriles The nitrile is refluxed with dilute hydrochloric acid, and then distil off the carboxylic acid

Reactions of Carboxylic acids

1. Can make primary alcohols Reduction with LiAlH4 (a powerful reducing agent) in dry ether

Carboxylic acids are weak acids

Weak acids split up in solution, but the positive and negative ions join back together again this is called an equilibrium CH3COOH(aq) CH3COO-(aq) + H+(aq)

They are only slightly ionised when they dissolve in water The aqueous hydrogen ions in the solutions of carboxylic acids means that they show characteristic reactions with metals, bases and carbonates

Reactions of Carboxylic acids

2. Neutralisation reactions Carboxylic acids are neutralised by aqueous alkalis to form salts and water CH3COOH + NaOH CH3COONa + H2O

Reactions of Carboxylic acids

2. Neutralisation reactions Carboxylic acids react with carbonates CO32- or hydrogencarbonates HCO3- to form a salt, CO2 and water

Reactions of Carboxylic acids

3. Reactions with Phosphorus(V) chloride PCl5 Reacts vigorously at room temp -OH group replaced with Cl atom forming an acyl chloride

The other product is HCl gas which fumes in moist air

Reactions of Carboxylic acids

4. Esterification Carboxylic acids react with alcohols to form Esters

Heated under reflux in the presence of an acid catalyst. We shall return to look at esters in more depth later on

Citric acid
Citric acid is found in the juice of all citrus fruits Citric acid contains 3 carboxyllic acid groups and has a molecular formula of C6H8O7

Determining the concentration of carboxylic acids

Via titration Can determine the amount of citric acid in fruit In a titration, 1mol citric acid reacts with 3mol sodium hydroxide when the indicator is phenolphthalein

To do.
1. Reactions of carboxylic acids worksheet
Questions 1 - 5

2. Hodder Edexcel Chemistry for A2 textbook

Pages 96 99 Answer questions 1-12

FINISH ALL OF THE ABOVE FOR HOMEWORK!