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9701 A Level Chemistry/ Topic 33 Carboxylic acids and derivatives (A Level)/ 5 interactive simulations/ drag to rotate 3D scenes

Carboxylic acids and derivatives (A Level), made interactive

Five simulations covering Topic 33: how chlorine, alkyl and phenyl groups change the strength of a carboxylic acid; the two acids that can be oxidised, methanoic and ethanedioic, tested with Tollens' reagent, Fehling's solution and acidified potassium manganate(VII); ethanoic acid turned into ethanoyl chloride with PCl5, PCl3 or SOCl2 in 3D; a hydrolysis race between ethanoyl chloride, chloroethane and chlorobenzene; and the addition-elimination mechanism of ethanoyl chloride with water, ethanol, ammonia and methylamine, stepped through in 3D with the curly arrows.

1. Substituents and acid strength 2D · 33.1

A carboxylic acid is only as strong as its anion is stable. Anything attached to the carboxyl carbon that pulls electron density away helps to spread the negative charge on the carboxylate ion, so the acid gives up its proton more readily. Anything that pushes electron density in does the opposite. Pick a group and watch the pKa and the charge change.

Group attached to the carboxyl carbon

acid
pKa (298 K)
Ka / mol dm−3
Ka compared with ethanoic acid
pH of 0.100 mol dm−3
effect of the group
Exam point: the smaller the pKa, the stronger the acid. Electron-withdrawing groups (Cl) stabilise the anion and strengthen the acid, and more chlorine atoms means a larger effect; electron-releasing alkyl groups destabilise the anion and weaken it. Always link the strength of the acid to the stability of its anion.

2. Acids that can be oxidised 2D · 33.1

Most carboxylic acids are already fully oxidised and do not react with oxidising agents. Two are different: methanoic acid has a hydrogen on the carboxyl carbon, like an aldehyde, and ethanedioic acid has two carboxyl groups joined together. Choose an acid and a reagent, add the acid and warm the tube.

Acid

Reagent

OBSERVATION
choose and press the button
EQUATION
Conditions: Tollens' reagent (silver nitrate in aqueous ammonia) warmed in a water bath; Fehling's solution (copper(II) in alkali) heated gently; potassium manganate(VII) acidified with dilute sulfuric acid and warmed to about 60 °C. In every case the carbon-containing product is carbon dioxide.

3. Making an acyl chloride 3D · 33.2

To make ethanoyl chloride, the OH of the carboxyl group is swapped for a chlorine atom. Three reagents will do it: phosphorus(V) chloride, phosphorus(III) chloride and sulfur dichloride oxide (thionyl chloride). Pick one and step through to see the products and the conditions.

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Chlorinating agent

STEP
CONDITIONS
BY-PRODUCTS
EQUATION
Exam point: all three reagents must be used dry, because acyl chlorides and the reagents themselves react with water. Thionyl chloride is often preferred because both by-products are gases and escape, leaving the ethanoyl chloride easy to separate. These are the same reagents that convert alcohols to chloroalkanes.

4. The hydrolysis race 2D · 33.2

Three compounds all contain a carbon-chlorine bond, but they behave very differently with cold water. Add a few drops of each to water, then test the solution with acidified silver nitrate to see whether any chloride ions were released.

Do it in order

Explain a compound

OBSERVATION
EQUATION
Exam point: ethanoyl chloride hydrolyses vigorously in cold water, with steamy fumes of HCl. Chloroethane is hydrolysed only slowly, and needs heat and aqueous alkali to react at a useful rate. Chlorobenzene does not react. White AgCl(s) shows chloride ions are present in solution.

5. Addition-elimination 3D · 33.2

Acyl chlorides react with nucleophiles in two stages. The nucleophile adds to the carbonyl carbon, and then the chlorine is eliminated as the carbon-oxygen double bond is restored. Pick a nucleophile and step through, watching the curly arrows.

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Nucleophile attacking ethanoyl chloride

STEP
PRODUCT
TYPE OF PRODUCT
EQUATION
Conditions: all of these reactions happen at room temperature and are vigorous. Ammonia and amines are used in excess, because a second molecule removes the proton and the HCl formed ends up as a salt. The mechanism is nucleophilic addition-elimination.
TheLucidSTEM · Cambridge International A Level Chemistry 9701 · Topic 33 Carboxylic acids and derivatives (A Level). Every scene runs in the browser; drag to rotate 3D scenes, wheel to zoom. Values are standard textbook data rounded for teaching.

About this lab: Carboxylic acids and derivatives (A Level)

Five interactive simulations for Cambridge A Level Chemistry 9701 topic 33 Carboxylic acids and derivatives: the pKa and charge distribution of substituted carboxylate ions, a bench for the oxidation of methanoic and ethanedioic acids with Tollens' reagent, Fehling's solution and acidified potassium manganate(VII), a 3D view of ethanoic acid becoming ethanoyl chloride with phosphorus pentachloride, phosphorus trichloride or thionyl chloride, a hydrolysis race of ethanoyl chloride against chloroethane and chlorobenzene with silver nitrate and bond polarity, and the nucleophilic addition-elimination mechanism of ethanoyl chloride with water, ethanol, ammonia and methylamine in 3D with curly arrows.

Five simulations covering Topic 33: how chlorine, alkyl and phenyl groups change the strength of a carboxylic acid; the two acids that can be oxidised, methanoic and ethanedioic, tested with Tollens' reagent, Fehling's solution and acidified potassium manganate(VII); ethanoic acid turned into ethanoyl chloride with PCl5, PCl3 or SOCl2 in 3D; a hydrolysis race between ethanoyl chloride, chloroethane and chlorobenzene; and the addition-elimination mechanism of ethanoyl chloride with water, ethanol, ammonia and methylamine, stepped through in 3D with the curly arrows.

Carboxylic acids and derivatives (A Level) is a free, browser-based simulation for Cambridge International AS & A Level Chemistry 9701 (topic 33 Carboxylic acids and derivatives). The course is assessed in Paper 1 (Multiple Choice (AS)), Paper 2 (AS Structured), Paper 3 (Advanced Practical), Paper 4 (A Level Structured), Paper 5 (Planning, Analysis, Evaluation). Syllabus for examination in 2025-2027. There are 5 tabs, each a self-contained experiment with its own controls and live readings, and nothing to install: it runs on a laptop, tablet or classroom projector.

Syllabus coverage

Full syllabus map: A Level Chemistry 9701 topic 33.

How to use this simulation

  1. 1. Substituents and acid strength. A carboxylic acid is only as strong as its anion is stable.
  2. 2. Acids that can be oxidised. Most carboxylic acids are already fully oxidised and do not react with oxidising agents.
  3. 3. Making an acyl chloride. To make ethanoyl chloride, the OH of the carboxyl group is swapped for a chlorine atom.
  4. 4. The hydrolysis race. Three compounds all contain a carbon-chlorine bond, but they behave very differently with cold water.
  5. 5. Addition-elimination. Acyl chlorides react with nucleophiles in two stages.
  6. The buttons at the end of the tab strip give the scene the whole window (Full screen, Hide controls) and, on a dark stage, a projector-friendly palette (Light scene). Many scenes also have drag handles: drag them to change the set-up directly.

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