有机化学课件Chapter 10 Carbohydrates教程文件.pptVIP

Chapter 10 Carbohydrates Teaching Objectives and Requirements Understand: Classification, Chirality, Disaccharides, Polysaccharides. Grasp: Hemiacetals and Hemiketals, Reduction of Monosaccharides, Oxidation of Carbohydrates, Glycosides. Key points and Main Areas of Difficulty Hemiacetals and Hemiketals, Reduction of Monosaccharides, Oxidation of Carbohydrates, Glycosides. 10.1 Classification of Carbohydrates Carbohydrates (碳水化合物) are polyhydroxy aldehydes or ketones or compounds that can be hydrolyzed to form them. Aldoses or ketoses Suffix –ose:carbohydrate Prefix aldo:aldehyde keto:ketone Carbohydrate: (碳水化合物) Cm(H2O)n Glucose: (葡萄糖) C6H12O6 C6(H2O)6 Poly-hydroxylated aldehydes and ketones Sugars: The sugar, Starch, Cellulose Nucleic acid Monosaccharides： a simple carbohydrate that can’t be converted into smaller sugar by hydrolysis. Photosynthesis: (光合作用) Cellulose, starch Carbohydrates Monosaccharides (simple sugars) (单糖) Oligosaccharides (寡糖) Polysaccharides (多糖) Ex. Glucose, fructose(果糖) 10.2 Chirality of Monosaccharides Fischer projection formula:the carbon chain is represented by a vertical line. Vertical line represent bonds going into the page. Horizontal line represent bonds coming out of the page. The carbonyl carbon atom the most oxidized carbon atom:near the “top” D and L Designation of saccharides * Glyceraldehyde (甘油醛) (+)- (R)- D-Glyceraldehyde * L-Glyceraldehyde (S)-(-)-Glyceraldehyde D: dextrorotation L: levorotation L-Glyceraldehyde D-Glyceraldehyde (D)-Ribose (D)-Glucose (D)-Fructose (D)-Glucose (L)-Glucose (D)-Fructose (L)-Fructose In Fischer projection, the -OH group at the lowest stereocenter: (D) for right; (L) for left. 10.3 Hemiacetal and Hemiketals Intramolecular nucleophilic addition: the formation of a five- or six- membered cyclic hemiacetal. D-Glucose D-Glucose, pyranose (吡喃糖) Haworth projection Conversion from Fischer projection to Haworth projection: 1 2 3 4 5 Monosaccharide Anomers (差