lecture 19 - Chapter 19. Aldehydes and Ketones:...

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Chapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions Based on McMurry’s Organic Chemistry , 7 th edition
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2 Aldehydes and Ketones 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
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3 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 An understanding of their properties is essential
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4 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, use the suffix carbaldehyde. See Table 19.1 for common names
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5 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
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6 Ketones with Common Names IUPAC retains well-used but unsystematic names for a few ketones
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7 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 The prefix oxo - is used if other functional groups are present and the doubly bonded oxygen is labeled as a substituent on a parent chain
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8 19.2 Preparation of Aldehydes and Ketones Preparing Aldehydes Oxidize primary alcohols using pyridinium chlorochromate Alkenes with a vinylic hydrogen can undergo oxidative cleavage when treated with ozone, yielding aldehydes Reduce an ester with diisobutylaluminum hydride (DIBAH)
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9 Preparing Ketones Oxidize a 2° alcohol Many reagents possible: choose for the specific situation (scale, cost, and acid/base sensitivity)
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10 Ketones from Ozonolysis Ozonolysis of alkenes yields ketones if one of the unsaturated carbon atoms is disubstituted
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11 Aryl Ketones by Acylation Friedel–Crafts acylation of an aromatic ring with an acid chloride in the presence of AlCl 3 catalyst
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12 Methyl Ketones by Hydrating Alkynes Hydration of terminal alkynes in the presence of Hg 2 + (catalyst: Section 8.4)
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13 19.3 Oxidation of Aldehydes and Ketones CrO 3 in aqueous acid oxidizes aldehydes to carboxylic acids efficiently Silver oxide, Ag 2 O, in aqueous ammonia (Tollens’ reagent) oxidizes aldehydes (no acid)
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14 Hydration of Aldehydes Aldehyde oxidations occur through 1,1-diols
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This note was uploaded on 09/06/2009 for the course CHEM chem 12 AB taught by Professor Adamczeski during the Spring '09 term at San Jose City College.

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lecture 19 - Chapter 19. Aldehydes and Ketones:...

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