Química Orgánica 1 · Transformaciones de alquinos
Hydration of phenylacetylene to acetophenone
Condiciones: H₂O, H₂SO₄, HgSO₄ (cat.)
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Arrastra desde los electrones que se mueven hasta donde van, o toca uno y luego el otro. Cada flecha se revisa; Pista te ayuda cuando te atascas. No necesitas cuenta.
El mecanismo, paso a paso
Siguiente reproduce las flechas curvas de cada paso y las explica. Los pasos escritos están abajo.
Leer los 9 pasos escritos
Mercury(II) adds to the triple bond
Hg²⁺ is the electrophile. A π pair bonds to mercury at the carbon that leaves the positive charge on the better-stabilized carbon (Markovnikov orientation). Mercury keeps one positive charge.
Las flechas curvas
- One alkyne π pair forms the C–Hg bond.
Water captures the vinyl cation
A water lone pair bonds to the cationic carbon, so oxygen ends up on the more substituted carbon.
Las flechas curvas
- A water lone pair bonds to the positive carbon.
Deprotonate the oxonium ion
Solvent water removes a proton from the oxonium ion, giving a neutral mercury-substituted enol.
Las flechas curvas
- A water lone pair takes the O–H proton.
- The O–H pair stays on oxygen, which becomes neutral.
Protonate the mercury-bearing carbon
Hydronium protonates the enol carbon that carries mercury; the oxygen lone pair forms a C=O π bond as it happens, so no free carbocation forms.
Las flechas curvas
- The C=C π pair takes a proton from hydronium.
- The O–H pair stays on water.
- An oxygen lone pair forms the C=O π bond.
Mercury(II) leaves
The C–Hg pair becomes a new C=C π bond and the C=O π pair returns to oxygen, releasing Hg²⁺ (the catalyst) and an ordinary enol.
Las flechas curvas
- The C–Hg bond pair forms the C=C π bond; mercury leaves as Hg²⁺.
- The C=O π pair moves back onto oxygen.
Why O goes next to the ring
Markovnikov orientation with an aryl group.
Protonate the enol at carbon
Acid-catalysed tautomerization begins: the enol C=C π pair takes a proton from hydronium at carbon while the oxygen lone pair forms C=O.
Las flechas curvas
- The enol π pair takes a proton from hydronium.
- The O–H pair stays on water.
- An oxygen lone pair forms the C=O π bond.
Deprotonate the carbonyl oxygen
Water removes the O–H proton of the protonated ketone, giving the neutral carbonyl and regenerating hydronium.
Las flechas curvas
- A water lone pair takes the proton on oxygen.
- The O–H pair stays on oxygen.
The ketone
The keto form is far more stable than the enol (C=O is stronger than C=C), so the product is the ketone. Hg²⁺ and hydronium are regenerated: both are catalysts.
Qué vas a practicar
Draw Hg²⁺-catalysed hydration of phenylacetylene, with oxygen on the benzylic carbon, and the tautomerization of the enol to acetophenone.
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