Timeline for Why does the reduction of a Weinreb amide give an aldehyde instead of an amine?
Current License: CC BY-SA 3.0
9 events
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| Jun 24, 2017 at 14:52 | history | edited | cfcief | CC BY-SA 3.0 |
added 144 characters in body
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| Jun 23, 2017 at 9:26 | comment | added | orthocresol | It would be excellent if you could include that last comment in your answer somehow. | |
| Jan 8, 2016 at 22:09 | comment | added | cfcief | Good point. Due to the good affinity of oxygen with metals (for instance, Al), the oxygen atom next to the nitrogen may actually form a O - - - Al - - - -O complex, which stabilizes the intermediate state. It is after the hydrolysis that the aldehyde is formed, thus preventing the over reduction to an alcohol. | |
| Jan 8, 2016 at 21:40 | comment | added | jerepierre | If the methoxylamide anion leaves in the course of the reaction, then the aldehyde would be formed in the presence of LiAlH4. The aldehyde is much more reactive than an amide, so it would be reduced to an alcohol. This is precisely what the Weinreb amide tries to avoid. | |
| Jan 8, 2016 at 21:34 | comment | added | cfcief | You'll have to ask my chemistry teacher for them. | |
| Jan 8, 2016 at 21:08 | comment | added | Mithoron | Where did you get such nice pictures? | |
| Jan 8, 2016 at 19:57 | review | First posts | |||
| Jan 8, 2016 at 20:11 | |||||
| Jan 8, 2016 at 19:55 | vote | accept | RobChem | ||
| Jan 8, 2016 at 19:54 | history | answered | cfcief | CC BY-SA 3.0 |