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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Chaste on September 28, 2009, 08:49:35 AM

Title: how to convert CN to CH3?
Post by: Chaste on September 28, 2009, 08:49:35 AM

as above.

would this method work?

1.reduce using LiAlH4 gives primary amine
2.adding of NaNO2. gives
3.addition of h2O removes nitrogen molecule? gives an primary alcohol.
4.dehydration to give alkene
5.hydrogenation to give alkane.

Title: Re: how to convert CN to CH3?
Post by: sjb on September 28, 2009, 04:54:09 PM

Does seem a very long way around the houses, with plenty of opportunity for things to go wrong. Did you have a particular cyanide in mind?

Title: Re: how to convert CN to CH3?
Post by: Dan on September 29, 2009, 05:29:08 AM

Why not just convert the nitrile to an aldehyde and use a Wolff-Kischner, Clemmenson or Mozingo (thioacetal) reduction to obtain the methyl group?

Title: Re: how to convert CN to CH3?
Post by: Chaste on September 29, 2009, 09:53:17 AM

Quote from: Dan on September 29, 2009, 05:29:08 AM

Why not just convert the nitrile to an aldehyde and use a Wolff-Kischner, Clemmenson or Mozingo (thioacetal) reduction to obtain the methyl group?

so just add DIBAL to CN to obtain CHO. thanks.

anyway, the answer is given in organic chem by jonathan clayden, warren.... pg 650.

i just wanted someone to correct me if i went the wrong way.