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9701 A Level Chemistry/ Topic 30 Arenes/ 5 interactive simulations/ drag to rotate 3D scenes

Arenes, made interactive

Five simulations covering Topic 30: the delocalised ring of benzene built from six p orbitals in 3D, electrophilic substitution stepped through with curly arrows and the Wheland intermediate for nitration and bromination, a reagent bench for nitration, halogenation and the Friedel-Crafts reactions, methylbenzene reacting at the ring or on the side chain depending on the conditions, and the directing effects that decide where a second group goes.

1. The delocalised ring 3D · 30.1

Each carbon in benzene uses three sp² orbitals to make sigma bonds, all in one flat plane at 120°. That leaves one p orbital per carbon pointing straight up and down. Switch on the p orbitals, then let them overlap sideways and watch the six electrons spread into a ring above and below the plane.

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Show

C–C BOND LENGTH
C–C–C ANGLE
π ELECTRONS
ΔH WITH 3H₂
Exam point: all six C–C bonds are 0.140 nm, between a single (0.154 nm) and a double (0.134 nm). Hydrogenation of benzene gives −208 kJ mol⁻¹, about 150 kJ mol⁻¹ less exothermic than three C=C bonds would give, so benzene is that much more stable.

2. Electrophilic substitution 3D · 30.1

The pi cloud above the ring is rich in electrons, so benzene attacks electrophiles. Choose nitration or bromination and step through it: make the electrophile, let the ring attack it, see the horseshoe intermediate with its delocalised positive charge, then lose H⁺ to get the ring back.

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Reaction

STEP
EQUATION
Nitration: concentrated HNO₃ with concentrated H₂SO₄, 25–60°C. Bromination: Br₂ with anhydrous FeBr₃ or AlBr₃ (a halogen carrier). In both the catalyst is regenerated in the last step.

3. Reagent bench 2D · 30.1

Every electrophilic substitution of benzene follows the same pattern: a catalyst makes a strong electrophile from a reagent that is not electrophilic enough by itself. Pick a reagent set, see the conditions, the electrophile and the product, then try leaving the catalyst out.

Reagent set

TEMPERATURE
ELECTROPHILE
PRODUCT
Conditions: nitration 25–60°C; halogenation at room temperature with an anhydrous halogen carrier; Friedel-Crafts reactions need anhydrous AlCl₃ and dry conditions. The temperature slider only changes the outcome for nitration.

4. Methylbenzene: ring or side chain? 3D · 30.1

Methylbenzene has two places to react: the ring and the methyl group. The conditions decide which. UV light with chlorine attacks the side chain by free radicals; a halogen carrier in the dark attacks the ring by electrophiles; hot alkaline potassium manganate(VII) oxidises the side chain to a carboxylic acid.

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Conditions

REACTION TYPE
REAGENTS
PRODUCT
Exam point: free-radical substitution needs UV light and no catalyst; electrophilic substitution needs a halogen carrier and no UV. Alkaline KMnO₄ oxidises any alkyl side chain with a benzylic hydrogen to COOH, and the ring survives.

5. Directing effects 2D · 30.1

A group already on the ring decides where the next one goes. Electron-donating groups push the next electrophile to positions 2, 4 and 6; electron-withdrawing groups push it to 3 and 5. Choose a group, then choose a position to attack and see whether the intermediate can cope with it.

Group already on the ring

Attack at position

DIRECTS TO
RING IS
SECOND NITRATION GIVES
Exam point: 2,4-directing groups (OH, NH₂, alkyl) donate electron density and activate the ring; 3-directing groups (NO₂, COOH, CHO) withdraw it and deactivate the ring. You can also click a position on the ring.
TheLucidSTEM · Cambridge International A Level Chemistry 9701 · Topic 30 Arenes. 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: Arenes

Five interactive simulations for Cambridge A Level Chemistry 9701 topic 30 Arenes: the sigma skeleton, p orbitals and pi doughnut of benzene in 3D with bond lengths and the 150 kJ per mole delocalisation energy, electrophilic substitution of benzene by NO2+ and Br+ stepped through with curly arrows and the horseshoe intermediate, a reagent bench for nitration, bromination and Friedel-Crafts alkylation and acylation with the electrophile each one generates, methylbenzene showing side-chain free-radical substitution in UV light against ring substitution with a halogen carrier plus oxidation to benzoic acid, and a 2,4-directing against 3-directing explorer that names the product of a second nitration.

Five simulations covering Topic 30: the delocalised ring of benzene built from six p orbitals in 3D, electrophilic substitution stepped through with curly arrows and the Wheland intermediate for nitration and bromination, a reagent bench for nitration, halogenation and the Friedel-Crafts reactions, methylbenzene reacting at the ring or on the side chain depending on the conditions, and the directing effects that decide where a second group goes.

Arenes is a free, browser-based simulation for Cambridge International AS & A Level Chemistry 9701 (topic 30 Hydrocarbons). 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 30.

How to use this simulation

  1. 1. The delocalised ring. Each carbon in benzene uses three sp² orbitals to make sigma bonds, all in one flat plane at 120°.
  2. 2. Electrophilic substitution. The pi cloud above the ring is rich in electrons, so benzene attacks electrophiles.
  3. 3. Reagent bench. Every electrophilic substitution of benzene follows the same pattern: a catalyst makes a strong electrophile from a...
  4. 4. Methylbenzene: ring or side chain? Methylbenzene has two places to react: the ring and the methyl group.
  5. 5. Directing effects. A group already on the ring decides where the next one goes.
  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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