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Nucleophilic Addition of Hydrogen Cyanide to Carbonyls: Mechanism and Product Formation

This reaction involves the addition of hydrogen cyanide (HCN) to carbonyl compounds to form hydroxynitriles. The conditions and reagents required are NaCN(aq) and H2SO4(aq) supplying CN- and H+, respectively, at room temperature and pressure. The nucleophilic addition mechanism includes C.N. attacking the carbonyl carbon. Illustration and naming of products from the reactions with ethanal, propanone, and 2-methylpropanal are essential in this reaction study.

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Nucleophilic Addition of Hydrogen Cyanide to Carbonyls: Mechanism and Product Formation

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Presentation Transcript

  1. Reaction of carbonylswith hydrogen cyanide (H+CN-) to form hydroxynitriles Conditions / Reagents NaCN (aq) andH2SO4(aq) supplies H+ supplies the CN- Room temperature and pressure

  2. Nucleophilic Addition Mechanism C N - O + O H O C CH3 C CN CH3 CH3 C CN CH3 CH3 CH3 CN hydrogen cyanide with propanone NaCN (aq) is a source of cyanide ions fromH2SO4 (aq) H+ 2-hydroxy-2-methylpropanenitrile

  3. HOMEWORK • Draw the mechanism for the reaction of HCN with • ethanal • propanone • 2-methyl propanal • In each case give the full graphical formulae of the organic products and their names.

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