CHEMISTRY 226 LECTURE OUTLINE #12 WEEK OF MARCH 31, 2008 1. Special reactions for the synthesis of primary amines (cont.) b. The Hofmann rearrangement i. The reaction ii. Mechanistic details 2. Synthesis of amines by reduction reactions B. Reactions of amines 1. Reactions of amines as nucleophiles a. Addition to the carbonyl group b. Nucleophilic substitution with reactive CA derivatives c. Amines in SN2 reactions d. Complication: polyalkylation e. Hofmann exhaustive methylation 2. Reactions with nitrous acid a. Primary and secondary aliphatic amines b. Diazotization of primary aromatic amines: formation of ?second-generation? aromatic compounds 3. The Hofmann elimination [Recitation, week of April 7] a. Examples and mechanism b. Selectivity: the Hofmann Rule c. Application: the Hofmann degradation U N I T V I I I : T H E B U I L D I N G B L O C K S O F N A T U R E I. The Carbohydrates (Saccharides, Sugars) A. Structure and stereochemistry 1. Carbohydrate terminology 2. Classification of saccharides a. By functionality b. According to number of carbons 3. Stereochemical principles applied to the monosaccharides a. The four stereoisomers of 2,3,4-trihydroxybutanal (an aldotetrose) b. Simplification: D-sugars 4. Stereochemical relationships in the D-aldose family a. Natural sugars have the D-configuration b. Construction of the family tree B. Cyclization of monosaccharides 1. Review: intramolecular cyclization of 5-hydroxypentanal 2. Cyclization of D-glucose a. Cyclization to five- and six-membered rings b. Closer look at pyranose formation c. ?- and ?- anomers d. Conformational and stereochemical analysis of the pyranose form DeCamp Mark Microsoft Word - 226Wi08 OL12
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