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Mechanism Explainer

Step-by-step organic reaction mechanisms with electron-flow curvy arrows and textbook references.

50 credits per use

What it does

Describe a reaction in words, up to 500 characters: the starting materials, the reagents and any conditions. Or pick a textbook preset. Clara walks through the mechanism step by step. Every step shows the bond event, the curvy-arrow electron flow, the structural reasoning, and a hint for drawing it yourself.

Highlights

  • ✓Classification (SN1, SN2, E1, E2, addition, pericyclic, etc.)
  • ✓Stereochemistry: inversion, retention, racemisation — with the reason
  • ✓Thermodynamic vs kinetic control
  • ✓Textbook references (Clayden, March, etc.) per mechanism

What you get back

  • →Numbered steps with bond events and electron flow
  • →Drawing hints for each curvy arrow
  • →Classification + stereochemistry summary
  • →Energy / thermodynamic commentary
  • →Citations to chapters in standard textbooks

What it looks like

An illustration of the kind of answer Clara gives, laid out the way the live tool shows it.

atomly · Mechanism Explainer

Reaction

Solvolysis of (S)-3-bromo-3-methylhexane in water (hydrolysis under neutral, polar protic conditions).

SN1Racemisation

Step 1

Rate-determining
CH₃CH₂CCH₂CH₂CH₃H₃CBrslowCH₃CH₂CCH₂CH₂CH₃CH₃⊕+Br⊖

Curvy arrow: electrons of the C–Br bond depart with bromine

Bond event

Heterolytic cleavage of the C–Br bond. The substrate ionises to a tertiary carbocation (the 3-methylhexan-3-yl cation) and bromide.

Electron flow

Both electrons of the C–Br σ bond leave with bromine (heterolysis). C3 becomes sp² hybridised and trigonal planar, with an empty p orbital perpendicular to the plane of the three alkyl groups.

Reasoning

Tertiary substrates strongly favour SN1 because the cation is stabilised by hyperconjugation from seven β C–H bonds (three on the methyl group and two on each neighbouring CH₂) and by inductive donation from three alkyl groups. Water is polar protic: it stabilises both the developing cation (ion–dipole interactions) and the bromide (hydrogen bonding). This is the rate-determining step; by Hammond's postulate the transition state resembles the cation, so anything that stabilises the cation speeds up the reaction.

+2 more steps, classification, stereochemistry, and textbook references…

Example ask

“Solvolysis of (S)-3-bromo-3-methylhexane in water — what's the mechanism and what happens to the stereochemistry?”

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