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According to the table here, diisobutyl aluminium hydride can reduce amides to aldehydes but according to the data given to me by my teacher DIBAL.H cannot reduce: amides, acids, isocyanides and nitro groups.

It's I also given in my notes that DIBAL.H is parallel to $\ce{LiAlH4}$ as a reducing agent but it is more selective.

I would like to know if DIBAL.H is able to reduce these functional groups or not.

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  • $\begingroup$ en.wikipedia.org/wiki/Diisobutylaluminium_hydride - Seems the teacher underestimated it/ $\endgroup$ – Mithoron Aug 7 '18 at 19:27
  • $\begingroup$ Here are more references: organic-chemistry.org/chemicals/reductions/… DIBAL is definitely not LAH. $\endgroup$ – Zhe Aug 7 '18 at 20:04
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    $\begingroup$ Quite a few reagents will actually react like their more reactive "equivalent" if the conditions are right e.g. NaBH4 will reduce groups it allegedly doesn't, that LiAlH4 is used for. Solvent and temperature play a huge part. So DIBAL will reduce functionalities that "common knowledge" says it won't. Conditions just have to be right. $\endgroup$ – Beerhunter Aug 7 '18 at 20:42
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DIBAL-H does the following:

  1. Acid chlorides to aldehydes (Fast)
  2. $3^\circ$ amides to aldehydes
  3. Nitriles to aldehydes
  4. Ketones to $2^\circ$ alcohols
  5. Aldehydes to $1^\circ$ alcohols. (Slower)

Also, it works best in these solvents: THF, toluene.

We need to avoid solvents like alcohols, amines, strong acids and halogenated compounds.

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