I was recently studying reactions involving DIBALH (diisobutyl aluminium hydride) and saw that it's reaction with alkyl cyanide yielded R-CH2NHOH according to Jerry March whereas in Solomons the product mentioned is R-CHO (To note the reaction in Solomons also included Hexane and Water but I don't think they participate rather they provide medium for the reaction and for workup and stuff). Please tell the correct products and if multiple products are formed then their percentage yields and also the use of extra reagents used in the reaction in Solomons.

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    $\begingroup$ R-CH2NHOH looks quite improbable (if I read it right). N-O bonds do not form out of the blue, especially as you reduce stuff. $\endgroup$ – Ivan Neretin May 28 at 18:49
  • $\begingroup$ @IvanNeretin Yeah I think so too $\endgroup$ – StackUpPhysics May 28 at 18:51
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    $\begingroup$ Are you sure that the reduction was not of an oxime? Otherwise, probably a typo. $\endgroup$ – user55119 May 28 at 18:52
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    $\begingroup$ @user55119 I'll recheck the book and update. However this is what was told to us by our teacher $\endgroup$ – StackUpPhysics May 28 at 18:52
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    $\begingroup$ Dibal-H reduces nitrile to imine, which on hydrolysis produces the aldehyde. It is possible to do a non-hydrolytic work-up to and isolate the imine and perhaps due to some typo, this is what is referred to. I can see no way you can form a hydroxylamine $\endgroup$ – Waylander May 28 at 19:12

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