Alkyne hydration and enol-to-carbonyl conversion
Adding hydration equivalents to an alkyne initially produces an enol, which can tautomerize to a carbonyl compound.
Key knowledge
Adding hydration equivalents to an alkyne initially produces an enol, which can tautomerize to a carbonyl compound. In representative terminal-alkyne reactions, mercury-catalysed hydration favours a methyl ketone, while suitable hydroboration–oxidation can favour an aldehyde. Unsymmetrical internal alkynes can give different regioisomeric products.
Conditions and scope
- The outcome depends on substrate and reaction system; enol/carbonyl equilibrium is not universally one-sided.
- Hydroboration requires a suitable reagent to control competing additions; no preparation recipe is supplied.
Sources · 1
References
Sources retain their recorded scope. A source link alone does not establish verification of every statement.
Evidence and review
Read enol intermediate, terminal versus internal products and bulky-borane control; excluded source's 1-butene terminal-alkyne typo and almost-never-isolated enol universality.
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Entry details
Permanent link to this entry ↗- Record identity
- uni-chem-alkyne-hydration
- Revision
- core.1
- Structured reference record
- University core expansion