Alkylation of a thiol
A thiol or its anion attacks an alkyl halide and takes its carbon, leaving a thioether.
What it needs, and what it gives
- Reaction class
- Substitution
- A mild base to make the thiolate; room temperature is usually enough.
- balanced — the co-products are written out, not dropped
- Mechanism
- none written
How it is thought to happen
The transformation is applied and tested, but no canonical pathway has been written for it yet. Rather than generate a plausible-looking set of arrows, the platform offers nothing here. What it does claim — which bonds change — is read from the transformation itself and does not depend on a mechanism.
Try it on your own structures
Enter your reactants in the Reaction Lab. If this transformation matches what you drew, it is applied and the outcome is shown next to the records that back it — with the count of documented reactions doing the same thing on substrates like yours, rather than a confidence score.
Other substitution transformations
Substitution by an anionic nucleophile
An anion displaces the halide from the back, turning the carbon over.
Epoxide opening under acid
An acid protonates the epoxide oxygen, and the ring opens at the carbon better able to carry positive charge — the more substituted one.
Epoxide opening under base
With no acid to open the ring first, the nucleophile has to attack it directly, so it goes to the carbon that is easier to reach — the less substituted one.
Solvolysis of a crowded halide
A crowded carbon lets its leaving group go before anything arrives. The flat intermediate is then attacked from either face, so any configuration it had is lost.
Alkylation of an amine
An amine attacks an alkyl halide and takes its carbon, becoming a more substituted amine.
Mitsunobu coupling
A phosphine and an azodicarboxylate turn an alcohol into a leaving group where it stands, and an acidic partner displaces it.