Organic Chemistry Chapter 12 Copyright@ The McGraw-Hill Companies, Inc. Permission required for reproduction or display
Organic Chemistry Chapter 12 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display
Carbon atoms have the ability to link together and form molecules made up of many carbon atoms The branch of chemistry that is the study of carbon-containing compounds is known as organic chemistry(有机化学) 13 million known organic compounds and 100,000 new ones are added annually Only 200,000-300,000 known inorganic compounds
• Carbon atoms have the ability to link together and form molecules made up of many carbon atoms. • The branch of chemistry that is the study of carbon-containing compounds is known as organic chemistry (有机化学). • 13 million known organic compounds and 100,000 new ones are added annually. • Only 200,000-300,000 known inorganic compounds
121 Hydrocarbons(碳氢化合物、烃) contain only carbon and hydrogen Hydrocarbons differ from each other by the number of carbon atoms methane CH4 Octane C8H18 polyethylene
12.1 Hydrocarbons (碳氢化合物、烃) contain only carbon and hydrogen • Hydrocarbons differ from each other by the number of carbon atoms. methane CH4 Octane C8H18 polyethylene
Hydrocarbons differ from each other also by the way carbon atoms connect to each other. Straight-chain hydrocarbon, branched hydrocarbon are ca∥ ed structural isomers(结构异构体). Structural isomers have Molecules having the same chemical formula but different structure different physical and chemical properties. The number of possible structural isomers for a chemical formula increases rapidly as the number of carbon atoms increases 3 for csh. 18 for coho. 75 for C10H2,366,319f0rC20H42 HHHH H H CH3H H H CH3 H H-C-C-C-C-C-H H-C-C-C-C-H H—C-C-C—H HHHH H HHH H H CH3 H n-pentane ISo-pentane Neo- pentane
• Hydrocarbons differ from each other also by the way carbon atoms connect to each other. Straight-chain hydrocarbon, branched hydrocarbon • Molecules having the same chemical formula but different structures are called structural isomers (结构异构体). Structural isomers have different physical and chemical properties. The number of possible structural isomers for a chemical formula increases rapidly as the number of carbon atoms increases: 3 for C5H12, 18 for C8H18, 75 for C10H22, 366,319 for C20H42. n-pentane iso-pentane Neo- pentane C H H H C C C C H H H H H H H H H C H H H C C C H CH3 H H H H H C H H H C C H CH3 CH3 H H
Carbon-based molecules can have different spatial orientations called conformations(构象) 滑操 Fig 12.2 three conformation for a molecule of n-pentane. The molecule looks different in each conformation but the five-carbon framework is the same in all three conformations In a sample of liquid n-pentane, the molecules are found in all conformations-not unlike a bucket of worms
Carbon-based molecules can have different spatial orientations called conformations (构象). Fig12.2 three conformation for a molecule of n-pentane. The molecule looks different in each conformation, but the five-carbon framework is the same in all three conformations. In a sample of liquid n-pentane, the molecules are found in all conformations- not unlike a bucket of worms
Hydrocarbons are usually from crude oil by fractional distillation(分馏) as Gasoline Fig 12.3 a 30°c-180°c schematic for Naphtha the fractional 110°c-195°c distillation of → Kerosene petroleum into 170°c-290°c its useful hydrocarbon Heating oil components 260°c-350°c Lubricating oil Heated 300°c-370°c crude oil→ at370°c Residue
Hydrocarbons are usually from crude oil by fractional distillation (分馏). Fig12.3 a schematic for the fractional distillation of petroleum into its useful hydrocarbon components
122 Unsaturated hydrocarbons(不饱和烃) contain multiple bonds saturated hydrocarbon Unsaturated hydrocarbon CH3CH2- CH2-CH3 CH2CH=CH—CH3 3 n-butane 2-butene
12.2 Unsaturated hydrocarbons (不饱和烃) contain multiple bonds CH3 CH CH CH3 2-butene saturated hydrocarbon Unsaturated hydrocarbon CH3－CH2－ CH2 － CH3 n-butane
Benzene(苯) and aromatic compounds(芳香化合物) Fig 12.8 (a)the double bonds of benzene, C6H6, are able to migrate around the ring. (b)for this reason, they are often represented by a circle within the ring
Benzene (苯) and aromatic compounds (芳香化合物) Fig 12.8 (a) the double bonds of benzene, C6H6, are able to migrate around the ring. (b) for this reason, they are often represented by a circle within the ring (a) (b)
C C toluene naphthalene 1. 4-dichlorobenzene
toluene naphthalene 1,4-dichlorobenzene Cl Cl
12.3 Organic molecules are classified by functional group(官能团) Important Functional Groups and Their Reactions ·醇、酚、醚、彐 Functional Group Name Typical Reactions Carbon-carbon Addition reactions with halogens, 胺、酮、醛、 double bond hydrogen halides, and water; hydrogenation to yield alkanes C≡C- Carbon-carbon Addition reactions with halogens, 酰胺、羧酸、 triple bond hydrogen halides: hydrogenation to 酯 Halogen Exchange reactions: (X= F CL. Br. 1) CHCH2Br+KI→→CH3CH2l+KBr -O-H Esterification(formation of an ester) with carboxylic acids: oxidation to aldehydes, ketones, and carboxylic Carbonyl Reduction to yield alcohols; oxidation 4 O of aldehydes to yield carboxylic acids -O-H Carboxyl Esteritication with alcohols: reaction with phosphorus pe ield acid chlorides -O-R Ester Hydrolysis to yield acids and alcohols Amine Formation of ammonium salts with R acid (R=H or hydrocarbon)
12.3 Organic molecules are classified by functional group (官能团) • 醇、酚、醚、 胺、酮、醛、 酰胺、羧酸、 酯