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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

Paste in any reaction — or pick a textbook preset — and 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

A real example of what Clara returns. (Rendered from the same data the live tool produces.)

atomly · Mechanism Explainer

Reaction

Solvolysis of (S)-2-bromo-2-methylbutane in water (hydrolysis under neutral, polar protic conditions).

SN1Racemisation

Step 1

Rate-determining
CH₃H₃CCBrCH₂CH₃CH₃H₃CCCH₂CH₃+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 and bromide.

Electron flow

Both electrons of the C–Br σ bond depart with bromine (heterolysis). The central carbon becomes sp² hybridised and trigonal planar, with an empty p orbital perpendicular to the molecular plane.

Reasoning

Tertiary substrates strongly favour SN1 because the resulting cation is stabilised by hyperconjugation from nine β C–H bonds and by σ-induction from three alkyl groups. Water is polar protic — it stabilises both the developing cation (by ion–dipole) and the bromide (by H-bonding). This is the rate-determining step; by Hammond's postulate the transition state resembles the cation, so anything that stabilises the cation accelerates the reaction.

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

Example ask

Solvolysis of (S)-2-bromo-2-methylbutane in water — what's the mechanism and what happens to the stereochemistry?

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