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Topic: Formation of 4-methylpyridine  (Read 1711 times)

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Offline fargogirl51

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Formation of 4-methylpyridine
« on: May 18, 2015, 09:21:12 PM »
Can anyone explain the mechanism for the formation of 4-methylpyridine using acetylaldehyde and ammonia? I know that they can combine to form either 4-methylpyridine or 2-methyloyridine but I'm having trouble visualizing the arrow pushing.
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Offline pgk

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Re: Formation of 4-methylpyridine
« Reply #1 on: May 19, 2015, 11:32:54 AM »
Let's say an aldol condensation, followed by a second aldol one. What products can be formed?
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Offline orgopete

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Re: Formation of 4-methylpyridine
« Reply #2 on: May 19, 2015, 04:27:10 PM »
Hint:

What is the product of a conjugate addition of acetaldehyde to the aldol product of acetaldehyde?

By the way, I think if acetaldehyde were replaced by other carbonyl compounds, they can lead to additional substituents on pyridine.
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