Química Orgânica 2 · Acetais, iminas e equilíbrios relacionados
Water releases an amine from an imine
Condições: Acetone N-methylimine in excess acidic water; follow hydrolysis and final methylammonium formation. One hydronium equivalent supplies the acid for this endpoint. Counterions are not drawn; no stereochemistry is assigned without bond markers.
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Arraste dos elétrons que se movem até onde eles vão, ou toque em um e depois no outro. Cada seta é verificada; Dica ajuda quando você travar. Não precisa de conta.
O mecanismo, passo a passo
Próximo mostra as setas curvas de cada passo e as explica. Os passos escritos estão abaixo.
Ler todos os 8 passos escritos
Move the electrons
Protonation gives a water-reactive iminium center; the catalyst water remains available as shuttle.
As setas curvas
- The base uses a lone pair to accept a proton from the O–H bond.
- The bond to hydrogen breaks, and its electrons stay on the atom losing the proton.
Move the electrons
Water adds to iminium carbon and the C=N pair restores the nitrogen lone pair.
As setas curvas
- The nucleophile uses a lone pair to form the new single bond.
- The π electrons move off carbon, keeping eight electrons around it.
Move the electrons
The water-derived oxonium becomes a neutral carbinolamine hydroxyl group.
As setas curvas
- The base uses a lone pair to accept a proton from the O–H bond.
- The bond to hydrogen breaks, and its electrons stay on the atom losing the proton.
Move the electrons
Protonation makes nitrogen a neutral-amine leaving group after C–N cleavage.
As setas curvas
- The base uses a lone pair to accept a proton from the O–H bond.
- The bond to hydrogen breaks, and its electrons stay on the atom losing the proton.
Move the electrons
The oxygen lone pair supplies C=O while the C–N pair goes to the leaving nitrogen.
As setas curvas
- A lone pair forms the new π bond.
- The leaving group takes the electrons from the single bond.
Move the electrons
Solvent removes the proton from the new carbonyl oxygen.
As setas curvas
- The base uses a lone pair to accept a proton from the O–H bond.
- The bond to hydrogen breaks, and its electrons stay on the atom losing the proton.
Move the electrons
Under the stated acidic endpoint, the released amine is trapped as its ammonium ion rather than left as an unrealistically unprotonated bulk product.
As setas curvas
- The base uses a lone pair to accept a proton from the O–H bond.
- The bond to hydrogen breaks, and its electrons stay on the atom losing the proton.
Products
The incoming water oxygen becomes the ketone oxygen. Nitrogen receives the C–N pair and ultimately has four sigma bonds with +1 charge; the hydronium protons end up in methylammonium and water.
O que você vai praticar
Complete imine hydrolysis and represent the acidic ammonium endpoint.
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