chapter19

chapter19 - Chapter 19. Aldehydes and Ketones: Nucleophilic...

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Unformatted text preview: Chapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions Based on McMurrys Organic Chemistry , 7 th edition 2 Contest for best Caption to a Cartoon CAPTION 1 Cow: He says it's a multiple halogenation of a methyl ketone in the presence of a base. Girl: Ho-lee shit, a talking cow. CAPTION 2 Girl: Once I was just like you, now I am genetically enhanced. 3 4 Aldehydes and Ketones 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 Pyridoxal is one of the three natural forms of vitamin B6 Cortisol is a vital hormone that is often referred to as the "stress hormone" as it is involved in the response to stress . It increases blood pressure , blood sugar levels and has an immunosuppressive action. In pharmacology , the synthetic form of cortisol is referred to as hydrocortisone , and is used as an antagonist in the treatment of allergies and inflammation as well as substitute supplementation in cortisol production deficiencies. 5 Example of an Aromatic Aldehyde Example of an Aromatic Aldehyde At room temperature benzaldehyde is a colorless liquid with a characteristic and pleasant almond-like odor: benzaldehyde is an important component of the scent of almonds, hence its typical odor. It is the primary component of bitter almond oil extract, and can be extracted from a number of other natural sources in which it occurs, such as apricot , cherry , and laurel leaves , peach seeds and, in a glycoside combined form ( amygdalin ), in certain nuts and kernels . Currently benzaldehyde is primarily made from toluene by a number of different processes. 6 Example of an Aromatic Ketone Example of an Aromatic Ketone Acetophenone is used to create fragrances that resemble almond , cherry , honeysuckle , jasmine , and strawberry . It is used in chewing gum. It can be found naturally in apple , cheese , apricot , banana , beef and cauliflower . 7 Why this Chapter? 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 8 19.1 Naming Aldehydes and Ketones 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 9 Naming Ketones 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 Based on McMurry, Organic Chemist 10 Nomenclature Priorities:...
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chapter19 - Chapter 19. Aldehydes and Ketones: Nucleophilic...

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