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Examples of Reactions with Grignard Reagents • Numbers above and below arrows mean the acid is not added until the Grignard reagent has reacted with the carbonyl compound. • When a reaction creates an asymmetric center from achiral reactants the product is a racemic mixture. © 2014 Pearson Education, Inc. Enzyme-Catalyzed Carbonyl Additions • If a product with an asymmetric center is formed in an enzyme-catalyzed reaction, only one enantiomer will be formed. • The enzyme blocks one face of the carbonyl compound so that only the other face is available for attack. © 2014 Pearson Education, Inc. Esters React with Grignard Reagents to Form Alcohols © 2014 Pearson Education, Inc. Acyl Chlorides React with Grignard Reagents to Form Alcohols © 2014 Pearson Education, Inc. Retrosynthetic Analysis • Work backwards to decide what alcohol and alkyl bromide could be used to synthesize a ketone. • Write the reaction scheme with all reagents and conditions. © 2014 Pearson Education, Inc. Reaction of Acetylide Ions with Carbonyl Compounds © 2014 Pearson Education, Inc. Reaction of Aldehydes and Ketones with Cyanide Ion © 2014 Pearson Education, Inc. Reactions of Cyanohydrins In base, decomposition to the carbonyl compound. In acid, hydrolysis to an α-hydroxycarboxylic acid. Reduction to a primary amine with an OH group on the β-carbon. © 2014 Pearson Education, Inc. Reactions of Aldehydes and Ketones with Hydride Ion © 2014 Pearson Education, Inc. Reactions of Acyl Chlorides with Hydride Ion © 2014 Pearson Education, Inc. A Weak Hydride Donor Reduces an Acyl Chloride to an Aldehyde © 2014 Pearson Education, Inc. Reactions of Esters with Hydride Ion © 2014 Pearson Education, Inc. Reactions of Carboxylic Acids with Hydride Ion © 2014 Pearson Education, Inc. A Weak Hydride Donor Reduces an Ester to an Aldehyde © 2014 Pearson Education, Inc. The Reactions of Amides with Hydride Ion © 2014 Pearson Education, Inc. Mechanism for the Reaction of an N-Substituted Amide with Hydride Ion © 2014 Pearson Education, Inc. Reductions Happen in Different Ways • An organic compound is reduced when hydrogen is added to it. • Hydrogen can be added as a hydride ion and a proton. • Hydrogen can be added as two hydrogen atoms. • Hydrogen can be added as two electrons and two protons. © 2014 Pearson Education, Inc. Hydrogen Can Be Added as a Hydride Ion and a Proton © 2014 Pearson Education, Inc. Catalytic Hydrogenation Reduces Carbon—Carbon Double and Triple Bonds © 2014 Pearson Education, Inc. Catalytic Hydrogenation Reduces Carbon—Nitrogen Double and Triple Bonds © 2014 Pearson Education, Inc.