有機化學第19ç« ï&f

有機化學第19ç« ï&f

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2009/5/5 1 Chapter 19. Aldehydes and Ketones 醛與酮 : Nucleophilic Addition Reactions 親核附加反應 Based on McMurry’s Organic Chemistry , 7 th edition Aldehydes and Ketones 醛與酮 Aldehydes (RCHO) and ketones (R 2 CO) are characterized by the the carbonyl functional group (C=O) The compounds occur widely in nature as intermediates in metabolism and biosynthesis 2 輔助酵素 副腎荷爾蒙之一種
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2009/5/5 2 Formaldehyde & Acetone 1.9 million tons 3 1.2 million tons Why this Chapter? Much of organic chemistry involves the chemistry of carbonyl compounds Aldehydes/ketones are intermediates in synthesis of pharmaceutical agents, biological pathways, numerous industrial processes 4 An understanding of their properties is essential
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2009/5/5 3 OUTLINE ± Naming Aldehydes and Ketones ± Preparation of Aldehydes and Ketones ± Oxidation of Aldehydes and Ketones ± Nucleophilic Addition Reactions of Aldehydes and Ketones ± Nucleophilic Addition of H 2 O: Hydration 5 ± Nucleophilic Addition of HCN: Cyanohydrin Formation OUTLINE ± Nucleophilic Addition of Grignard Reagents and Hydride Reagents: Alcohol Formation ± Nucleophilic Addition of Amines: Imine and Enamine Formation ± Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction ± Nucleophilic Addition of Alcohols: Acetal Formation 6
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2009/5/5 4 OUTLINE ± Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction ± The Cannizzaro Reaction: Biological Reductions ± Conjugate Nucleophilic Addition to α,β -Unsaturated Aldehydes and Ketones ± Spectroscopy of Aldehydes and Ketones 7 19.1 Naming Aldehydes and Ketones Aldehydes are named by replacing the terminal - e of the corresponding alkane name with al The parent chain must contain the CHO group (The CHO carbon is numbered as C1) If the CHO group is attached to a ring, 8 use the suffix carbaldehyde.
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2009/5/5 5 Aldehydes with Common Names 9 Naming Ketones Replace the terminal - e of the alkane name with – one Parent chain is the longest one that contains the ketone group Numbering begins at the end nearer the carbonyl carbon 10
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2009/5/5 6 Ketones with Common Names IUPAC retains well-used but unsystematic names for a few ketones 11 Ketones and Aldehydes as Substituents The R–C=O as a substituent is an acyl group, used with the suffix -yl from the root of the carboxylic acid CH 3 CO:acetyl;CHO: formyl;C 6 H 5 CO: benzoyl CO: acetyl; CHO: formyl; C The prefix oxo - is used if other functional groups 12 are present and the doubly bonded oxygen is labeled as a substituent on a parent chain
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2009/5/5 7 P. 19.1 13 P. 19.1 14
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2009/5/5 8 P. 19.2 15 19.2 Preparation of Aldehydes and Ketones 1. Oxidize primary alcohols using pyridinium chlorochromate Preparing Aldehydes 2. Ozonolysis alkenes and Cyclic alkenes 16
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2009/5/5 9 Preparing Aldehydes 3. Reduce an ester with diisobutylaluminum hydride (DIBAH with diisobutylaluminum hydride (DIBAH) 17 P. 19.3 18
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2009/5/5 10 P. 19.3 19 Preparing Ketones 1. Oxidize a 2 ° alcohol Many reagents possible: choose for the specific situation 20 (scale, cost, and acid/base sensitivity)
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2009/5/5 11 2. Ozonolysis of alkenes
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This note was uploaded on 11/11/2010 for the course CHE CH2005 taught by Professor 曹恒光 during the Spring '10 term at National Central University.

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有機化學第19ç« ï&f

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