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Experiment 5: Carboxylic acids: Preparation of benzoic acid

Introduction: Carboxylic acids are in vinegar salad dressing, which is a solution of acetic acid and water. Carboxylic acids are even in citric acid in grapefruit or lemon which gives them the sour taste. Carboxylic acids contain the carboxyl group, which is a combination of the carbonyl group and the hydroxyl group. The carboxyl functional group may be attached to an alkyl group or an aromatic group.

Benzoic acid, is a colourless crystalline solid and a simple aromatic carboxylic acid. It is mainly consumed in the production of phenol by oxidation decarboxylation at 300-400.

Oxidizing a primary alcohol can produce carboxylic acids. In this experiment, an aromatic carboxylic acids namely benzoic acid will be prepared by oxidizing benzyl alcohol, which is an aromatic alcohol with the formula. Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas. The oxidizing agent used is alkaline potassium permanganate (VII). Benzyl alcohol is refluxed with potassium permanganate in water. The mixture is hot filtered to remove manganese dioxide and then allowed to cool. Reaction between the alcohol with the oxidizing agent will produce sodium salt (i.e sodium benzoate), which on acidification with hydrochloric acid will produce benzoic acid.
Objective
To prepare benzoic acid from benzyl alcohol.

Materials
Sodium hydroxide, potassium permanganate, benzyl alcohol, concentrated hydrochloric acid, sodium sulphite, methyl orange solution, anti-bumping stone granules, Buchner funnel, 100 mL round bottom flask, and filter paper.
Methods
1. The mass of a small empty beaker was obtained.
2. 3 mL of benzyl alcohol was transferred in to the beaker and the mass of the alcohol was weighed.
3. 2g of sodium hydroxide was dissolved in 25 mL of distilled water, in a dry 100 mL of round bottom flask.
4. The weighed benzyl alcohol and 5g of potassium permanganate were added into the round

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