lecture 16.4 - Organic Chemistry William H Brown...

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16- 16-1 Organic Organic Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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16- 16-2 Aldehydes Aldehydes & & Ketones Ketones Chapter 16 Chapter 16
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16- 16-3 Oxidation of Aldehydes Oxidation of Aldehydes Aldehydes are oxidized to carboxylic acids by a variety of oxidizing agents, including H 2 CrO 4 They are also oxidized by Ag(I) in one method, a solution of the aldehyde in aqueous ethanol or THF is shaken with a slurry of silver oxide  CHO H 2 CrO 4 COOH Hexanal Hexanoic acid Vanillic acid Vanillin + + CH HO CH 3 O O O CH 3 O HO COH Ag 2 O THF, H 2 O NaOH Ag HCl H 2 O
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16- 16-4 Oxidation of Aldehydes Oxidation of Aldehydes Aldehydes are oxidized by O 2 in a radical chain reaction liquid aldehydes are so sensitive to air that they must be stored under N 2 Benzoic acid Benzaldehyde + CH O O COH 2 O 2 2
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16- 16-5 Oxidation of Ketones Oxidation of Ketones ketones are not normally oxidized by chromic acid they are oxidized by powerful oxidants at high temperature and high concentrations of acid or base H exanedioic acid (Adipic acid) Cyclohexanone (keto form) Cyclohexanone (enol form) HNO 3 O HO OH O O OH
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16- 16-6 Reduction Reduction aldehydes can be reduced to 1° alcohols ketones can be reduced to 2° alcohols the C=O group of an aldehyde or ketone can be reduced to a -CH 2 - group Aldehydes Can Be Reduced to Ketones Can Be Reduced to O O OH RCH RCH 2 OH RCH 3 RCR' RCHR' RCH 2 R'
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