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Catalytic Hydrogenation Reduces Carbon—Oxygen Double Bonds © 2014 Pearson Education, Inc. Dissolving Metal Reduction Reduces Carbon—Carbon Triple Bonds © 2014 Pearson Education, Inc. In a Chemoselective Reaction, One Functional Group Reacts Preferentially © 2014 Pearson Education, Inc. Aldehydes and Ketones Form Imines with Primary Amines © 2014 Pearson Education, Inc. Bonding in an Imine • The ∏ bond is formed by side-to-side overlap of a p orbital of carbon with a p orbital of nitrogen. • The ∏ bond is perpendicular to the orange orbitals. © 2014 Pearson Education, Inc. Mechanism for Imine Formation © 2014 Pearson Education, Inc. Intermediates in Imine Formation are Unstable • Imine formation is reversible because there are two protonated intermediates in the mechanism that can eliminate a group. • Imine formation can be pushed to completion by removing water as it is formed. © 2014 Pearson Education, Inc. Imine Hydrolysis is Irreversible • The amine is protonated in the acidic solution, so it is unable to react with the carbonyl compound. © 2014 Pearson Education, Inc. Formation of Imine Derivatives © 2014 Pearson Education, Inc. Aldehydes and Ketones Form Enamines with Secondary Amines © 2014 Pearson Education, Inc. Mechanism for Enamine Formation © 2014 Pearson Education, Inc. Enamine Hydrolysis is Irreversible • The amine is protonated in the acidic solution, so it is unable to react with the carbonyl compound. © 2014 Pearson Education, Inc. Reductive Amination • The unstable imine formed from ammonia is hydrogenated to an amine. • Imines and enamines are reduced to amines with NaBH3CN. © 2014 Pearson Education, Inc. Water Adds to an Aldehyde or Ketone to Form a Hydrate © 2014 Pearson Education, Inc. Why is There Such a Difference in the Keq Values? © 2014 Pearson Education, Inc. The Equilibrium Constant for the Reaction Depends on the Relative Stabilities of the Reactants and Products © 2014 Pearson Education, Inc. Proving the Mechanism for Hydrate Formation Isotopically labeled oxygen from water is incorporated into the ketone. © 2014 Pearson Education, Inc. The Reactions of Aldehydes and Ketones with Alcohols © 2014 Pearson Education, Inc. Acid-Catalyzed Hydrolysis of an Acetal © 2014 Pearson Education, Inc. Sugar Units in Carbohydrates are Held Together by Acetal Groups © 2014 Pearson Education, Inc.
