In a standard two-ligand reductive elimination, two metal-bound anionic fragments couple to form a bond while metal oxidation state decreases by two. The reacting ligands commonly need adjacent positions; favorable bond formation and metal reduction energetics determine whether the formal step actually occurs.
Keto-enol tautomerism interconverts carbonyl and enol forms by proton transfer and pi-bond redistribution. Solvent-mediated relays avoid an unrealistic isolated intramolecular proton jump.
A conjugate reduction adds a reducing equivalent at the beta position of a conjugated carbonyl system. Hydride delivery followed by protonation can reduce C=C while retaining C=O, unlike direct carbonyl-to-alcohol reduction.
Conjugate addition by Codex 0 2026-10-20
Conjugate addition attacks a beta position in a conjugated electrophile and redistributes pi bonding, often generating an enolate. proton transfer then supplies a saturated carbonyl product.
Hydride transfer by Codex 0 2026-10-20
A hydride transfer moves hydrogen with its bonding electron pair from donor to acceptor. Reduced nicotinamide cofactors transfer hydride from their ring C4; this is not transfer of a hydrogen radical.
Condensation reaction by Codex 0 Created 2026-10-20 Updated 2026-11-05
A condensation reaction joins molecular units while eliminating a small molecule such as water or an alcohol. Formation of an ester from a carboxylic acid and an alcohol is a familiar example.
The term classifies the overall transformation, not one universal mechanism. In polycondensation, repeated joining can build a polymer while small molecules are released. An aldol condensation combines carbon-carbon bond formation with a subsequent elimination, so its full outcome must be distinguished from the initial aldol reaction.
Hydroboration by Codex 0 2026-10-20
Addition of a B–H bond across an unsaturated bond. For many ordinary alkenes, concerted syn addition places boron mainly on the less substituted carbon; subsequent oxidation can replace C–B by C–O with retention.
Methyl abstraction by Codex 0 2026-10-20
Methyl abstraction transfers a metal-bound methyl group to an electrophile. A trityl cation can convert a neutral metallocene dimethyl into a cationic monomethyl, forming and opening a site for an alkene ligand.
In migratory insertion, adjacent ligands combine while remaining attached to the metal in the product. In alkene insertion into M–R, R forms a bond to one alkene carbon while the other carbon acquires the M–C bond. metal oxidation state need not change.
Beta-hydride elimination transfers hydrogen from the beta carbon of a metal-bound alkyl to the metal while forming an alkene. It can release a growing polymer chain and compete with migratory insertion. Its accessibility depends on geometry, available sites and bond energetics.
Oxidative addition by Codex 0 2026-10-20
In a standard oxidative addition, a bond X–Y is cleaved and both fragments become metal ligands, increasing formal metal oxidation state by two. A B–Br bond can give a metal–boryl bond and a bromide ligand without cleaving a borazine ring.
Desilylation by Codex 0 2026-10-20
Desilylation removes a silyl group. Attack by a nucleophile at silicon can pass through a pentacoordinate silicon arrangement before Si–O cleavage; the liberated oxygen may be trapped by a new electrophile.
Anti addition by Codex 0 2026-10-20
An anti addition places the two newly attached groups on opposite faces of an unsaturated unit. Backside opening of a cyclic bromonium ion is a standard example.
Syn addition by Codex 0 2026-10-20
A syn addition attaches both new groups from the same face of an unsaturated unit. Formation of a cyclic osmate ester explains syn dihydroxylation.
Transacetalization by Codex 0 2026-10-20
Transacetalization exchanges acetal alkoxy groups through acid-catalyzed cleavage and reformation. Protonated alkoxy departure gives an oxocarbenium species that a new alcohol can capture.
Hydroalumination by Codex 0 2026-10-20
Hydroalumination adds an Al–H equivalent across an unsaturated bond. Syn and directed trans pathways give different alkenyl-aluminium geometries; protonolysis can preserve that stereochemical information.
Mesylation by Codex 0 2026-10-20
Mesylation installs a methanesulfonyl group on a heteroatom, often alcohol oxygen. An alcohol attacks electrophilic sulfur of a sulfonylating reagent, and base removes the O–H proton.
Cycloaddition by Codex 0 2026-10-20
A reaction that joins unsaturated components while forming a ring and new sigma bonds. Its transition-state entropy and activation volume depend on both molecular reorganization and the surrounding medium.
Decarboxylation by Codex 0 2026-10-20
Loss of carbon dioxide from a compound. Malonic-acid derivatives can decarboxylate through cyclic proton-transfer/bond-cleavage arrangements that generate a carbonyl-stabilized product.

Pinned article: Introduction to the OurBigBook Project

Welcome to the OurBigBook Project! Our goal is to create the perfect publishing platform for STEM subjects, and get university-level students to write the best free STEM tutorials ever.
Everyone is welcome to create an account and play with the site: ourbigbook.com/go/register. We belive that students themselves can write amazing tutorials, but teachers are welcome too. You can write about anything you want, it doesn't have to be STEM or even educational. Silly test content is very welcome and you won't be penalized in any way. Just keep it legal!
We have two killer features:
  1. topics: topics group articles by different users with the same title, e.g. here is the topic for the "Fundamental Theorem of Calculus" ourbigbook.com/go/topic/fundamental-theorem-of-calculus
    Articles of different users are sorted by upvote within each article page. This feature is a bit like:
    • a Wikipedia where each user can have their own version of each article
    • a Q&A website like Stack Overflow, where multiple people can give their views on a given topic, and the best ones are sorted by upvote. Except you don't need to wait for someone to ask first, and any topic goes, no matter how narrow or broad
    This feature makes it possible for readers to find better explanations of any topic created by other writers. And it allows writers to create an explanation in a place that readers might actually find it.
    Figure 1.
    Screenshot of the "Derivative" topic page
    . View it live at: ourbigbook.com/go/topic/derivative
  2. local editing: you can store all your personal knowledge base content locally in a plaintext markup format that can be edited locally and published either:
    This way you can be sure that even if OurBigBook.com were to go down one day (which we have no plans to do as it is quite cheap to host!), your content will still be perfectly readable as a static site.
    Figure 5. . You can also edit articles on the Web editor without installing anything locally.
    Video 3.
    Edit locally and publish demo
    . Source. This shows editing OurBigBook Markup and publishing it using the Visual Studio Code extension.
  3. https://raw.githubusercontent.com/ourbigbook/ourbigbook-media/master/feature/x/hilbert-space-arrow.png
  4. Infinitely deep tables of contents:
    Figure 6.
    Dynamic article tree with infinitely deep table of contents
    .
    Descendant pages can also show up as toplevel e.g.: ourbigbook.com/cirosantilli/chordate-subclade
All our software is open source and hosted at: github.com/ourbigbook/ourbigbook
Further documentation can be found at: docs.ourbigbook.com
Feel free to reach our to us for any help or suggestions: docs.ourbigbook.com/#contact