Reducing Carboxylic Acid Derivatives with Hydride
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- Опубликовано: 12 сен 2024
- joechem.io/vid... for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link)
In this video, we'll talk about the various Hydride containing reagents we can use to reduce carboxylic acid derivatives. We'll identify the differences in reactivity and the benefits/drawbacks that each contain.
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in the third example (excess NaBH4) is there actually an oxygen between the 2 carbonyls? i wonder how it gets replaced with a carbon
Hey netspirit79,
So as stated in the video, I wanted to show the effect of the reduction on the left side of the molecule (to show that NaBH4 and the EtOH workup is alkene/alkyne safe). The left side of the molecule (the carbonyl carbon) is first attacked by H:-, an addition elimination mechanism follows, and the right side of the molecule is ejected as the leaving group when the tetrahedral intermediate collapses (which is a great LG because the carboxylate is resonance stabilized).
The result of the first attack is an aldehyde, which is then attacked AGAIN by ANOTHER H:-. This, after workup from the EtOH, produces the product shown, which still has 4 carbons, as seen in the left side of the reactant.
Did that make sense?
@@jOeCHEM Oh got it. Sorry, all clear!
@@netspirit79 glad it made sense! And also, thanks for watching
With the last example LiAlH4 would convert it to alcohol so why didn't you rather use a protecting group and add H2 in raney nickel
May you could do a video about methylparaben like of the mechanism from a benzoe acid to like the paraben? Bcs I have to write a documentary of 12 Pages and it‘s much more complicated than I thought it would be. Stupid mistake of my chemistry abilities😂 could you please help out?
nice