Lesson27 - Functional Groups With C=O and Related...

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Unformatted text preview: Functional Groups With C=O and Related Carbon-Heteroatom Multiple Bonds aldehyde N N NH 2 H 2 N N C O OH O O O O Cl O S O NH 2 O O O H O S ketone thioketone imine nitrile urea (or guanidine) carboxylic acid carboxylic ester carboxylic anhydride amide thioester acid chloride α β α , β ¡ unsaturated carbonyls The acyl group Chemistry of the Carbonyl Functional Group Electrophilic site: nucleophiles attack here Basic site: protons add here α Acidic hydrogen: deprotonation creates a nucleophile Leaving group (substitution Chemistry of the Carbonyl Functional Group Electrophilic site: nucleophiles attack here Basic site: protons add here α Acidic hydrogen: deprotonation creates a nucleophile Leaving group (substitution reactions) Types of Carbonyl Reactions I. Addition reactions Here the carbonyl serves as an ___________ electrophile The elements of “Nu-H” add across the C=O double bond Nu + H O C Nu H O C II. Substitution reactions Here the carbonyl serves as an ___________ and “X” is a ____________. electrophile leaving group The “X” group is replaced by the “Nu” group. This is substitution at an sp 2 carbon. O R X Nu O R Nu X Overall result is substitution of -H at the α-carbon by -E ....
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This note was uploaded on 01/25/2012 for the course CHEM 232 taught by Professor Miller during the Spring '08 term at University of Illinois, Urbana Champaign.

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Lesson27 - Functional Groups With C=O and Related...

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