Physics, Chemistry, Maths Forum

Reduction of acid derivatitves, oxidation

Reduction of acid derivatitves, oxidation

by Astitwa Lathe -
Number of replies: 2

If LiTri(O-t-Bu)AlH is used for reducing esters and nitrile,what will be the product? Also if DIBAL-H(Diisobutylaluminium hydride) is used for reducing acyl chloride, product?

PCC(pyridinium chloro chromate) oxidises primary alcohols  but will it work on secondary alcohols?

Please give information from where one can read about this.

In reply to Astitwa Lathe

Re: Reduction of acid derivatitves, oxidation

by Manish Verma -
When you are using hydride transfer agent other than LAH then your intention is to not to go upto alcohol but to stop at the intermediate.

Ester is less reactive in comparison to acyl chloride and nitrile is also difficult to reduce.  So, ideally one won't prefer a sterically hindered LtBAH with ester and nitrile.  One would rather prefer it with reactive acyl chloride.  DIBAH goes well with less reactive ester and nitrile.

However, if one does reverse things and uses DIBAH with acyl chloride then one can expect alcohol which LAH can also produce.  Also, if sterically hindered LtBAH is used with less reactive ester then one can expect very slow rate of reaction with it and with nitrile one can expect aldehyde at 0 deg C (generally reactions with these hydride transfer agents are done at -78 deg C).

I vaguely remember the Organic Chemistry text by McMurry J having some references.

Finally, PCC oxidises secondary alcohols to ketones just like Jones reagent does.  The difference lies in primary alcohols oxidation which you must be knowing very well.