Organic Chemistry Chapter 11 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

유기화학 입문 1. 유기화합물의 분류 2. 지방족 탄화수소 3. 방향족 탄화수소 4. 작용기의 화학 5. 카이랄성 : 분자의 손대칭성

11.1 Common Elements in Organic Compounds

11.1 Classification of Hydrocarbons

11.2 Alkanes Alkanes have the general formula C n H 2n+2 where n = 1,2,3,… only single covalent bonds saturated hydrocarbons because they contain the maximum number of hydrogen atoms that can bond with the number of carbon atoms in the molecule CH 4 C2H6C2H6 C3H8C3H8 methaneethanepropane

11.2 Structural isomers are molecules that have the same molecular formula but different structures

How many structural isomers does pentane, C 5 H 12, have? 11.2 CCCC C HHHHH H HHHHH H CCC C HCH 3 HH H HHHH H CC C H H H HH H n-pentane 2-methylbutane 2,2-dimethylpropane

11.2 Alkane Nomenclature 1.The parent name of the hydrocarbon is that given to the longest continuous chain of carbon atoms in the molecule. CH 3 CH 2 CHCH 2 CH methylheptane 2.An alkane less one hydrogen atom is an alkyl group. CH 4 CH 3 methane methyl

11.2 Alkane Nomenclature

11.2 Alkane Nomenclature 3.When one or more hydrogen atoms are replaced by other groups, the name of the compound must indicate the locations of carbon atoms where replacements are made. Number in the direction that gives the smaller numbers for the locations of the branches. CH 3 CHCH 2 CH methylpentane CH 3 CH 2 CHCH methylpentane

11.2 Alkane Nomenclature 4.Use prefixes di-, tri-, tetra-, when there is more than one alkyl branch of the same kind. CH 3 CH CH 2 CH ,3-dimethylhexane CH 3 CHCCH 2 CH ,3-dimethylhexane

11.2 Alkane Nomenclature 5.Use previous rules for other types of substituents. CH 3 CH CH 3 Br 1234 NO 2 2-bromo-3-nitrobutane CH 2 CHCH 3 Br 1234 NO 2 1-bromo-3-nitrobutane

What is the IUPAC name of the following compound? CH 3 CHCH 2 CHCH 2 CH 3 C2H5C2H5 CH 2 CH 3 2-methyl-4-ethyloctane What is the structure of 2-propyl-4-methylhexane? CH 3 CHCH 2 CHCH 2 CH 3 C3H7C3H7

11.2 It is 3,5-dimethyloctane! CH 3 CHCH 2 CHCH 2 CH 3 C3H7C3H7 2-propyl-4-methylhexane? CH 3 CHCH 2 CHCH 2 CH CH

11.2 Alkane Reactions CH 4 (g) + 2O 2 (g) CO 2 (g) + 2H 2 O (l)  H 0 = kJ Combustion Halogenation CH 4 (g) + Cl 2 (g) CH 3 Cl (g) + HCl (g) light Cl 2 + energy Cl + Cl Cl + CH H H H CH H H + HCl CH H H + Cl Cl CCl H H H + Cl

11.2 achiralchiral Enantiomer or Optical isomers 거울상 이성질체

11.2 Cycloalkanes Alkanes whose carbon atoms are joined in rings are called cycloalkanes. They have the general formula C n H 2n where n = 3,4,…

Cycloalkanes 11.2

기하 이성질체 Geometric isomers 11.2 Alkenes Alkenes have the general formula C n H 2n where n = 2,3,… contain at least one carbon-carbon double bond also called olefins CH 2 CHCH 2 CH 3 1-butene CH 3 CH CH 3 2-butene CC Cl HH CC H H cis-dichloroethylenetrans-dichloroethylene

Cis-Trans Isomerization in the Vision Process 11.2

Alkene Reactions Cracking Addition Reactions CH 2 CH 2 (g) + HBr (g) CH 3 CH 2 Br (g) CH 2 CH 2 (g) + Br 2 (g) CH 2 Br CH 2 Br (g) C 2 H 6 (g) CH 2 CH 2 (g) + H 2 (g) Pt catalyst

Regioselectivity of Hydrogen Halide Addition: Markovnikov's Rule When an asymmetrically substituted alkene reacts with a hydrogen halide, the hydrogen adds to the carbon that has the greater number of hydrogen substituents, and the halogen adds to the carbon that has the fewer hydrogen substituents. Br CH 3 CH 2 CHCH 3 + CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 CH 2 CH HBr Br acetic acid (80%)

acetic acid Br CH 3 CH 2 CHCH 3 CH 2 CH 3 CH 2 CH HBr (80%) Regioselectivity of Hydrogen Halide Addition: Markovnikov's Rule Example 1 CH 3 CH 2 CH—CH 3 + Br – + CH 3 CH 2 CH 2 —CH 2 + primary carbocation is less stable: not formed

CH 3 C Br (90%) C C acetic acid HBr CH 3 H H Regioselectivity of Hydrogen Halide Addition: Markovnikov's Rule Example 2

0°C CH 3 Cl CH 3 (100%) HCl Regioselectivity of Hydrogen Halide Addition: Markovnikov's Rule Example 3 CH 3 H H + +H H secondary carbocation is less stable: not formed

11.2 Alkynes Alkynes have the general formula C n H 2n-2 where n = 2,3,4,… contain at least one carbon-carbon triple bond 1-butyne2-butyne CH CCH 2 CH 3 CC Production of acetylene CaC 2 (s) + 2H 2 O (l) C 2 H 2 (g) + Ca(OH) 2 (aq)

11.2 Alkyne Reactions Addition Reactions Hydrogenation CH CH (g) + H 2 (g) CH 2 CH 2 (g) CH CH (g) + HBr (g) CH 2 CHBr (g) CH CH (g) + Br 2 (g) CHBr CHBr (g) CH CH (g) + 2Br 2 (g) CHBr 2 CHBr 2 (g)

Chemistry In Action: Ice That Burns

11.3 Aromatic Hydrocarbons C C C CC C H H H H H H C C C CC C H H H H H H

11.3 Aromatic Compound Nomenclature CH 2 CH 3 ethylbenzene Cl chlorobenzene NH 2 aminobenzene NO 2 nitrobenzene Br 1,2-dibromobenzene Br 1,3-dibromobenzene

11.3 Aromatic Compound Reactions H H H H H H Br H H H H H + HBr+ Br 2 FeBr 3 catalyst H H H H H H CH 2 CH 3 H H H H H + HCl+ CH 3 CH 2 Cl AlCl 3 catalyst Substitution reaction

11.3 Polycyclic Aromatic Hydrocarbons

11.4 Functional Group Chemistry Alcohols contain the hydroxyl functional group and have the general formula R-OH.

C 6 H 12 O 6 (aq) 2CH 3 CH 2 OH (aq) + 2CO 2 (g) enzyme CH 2 CH 2 (g) + H 2 O (g) CH 3 CH 2 OH (g) H 2 SO 4 Biological production of ethanol Commercial production of ethanol Metabolic oxidation of ethanol CH 3 CH 2 OH CH 3 CHO + H 2 alcohol dehydrogenase 11.4

Functional Group Chemistry Ethers have the general formula R-O-R’. CH 3 OH + HOCH 3 CH 3 OCH 3 + H 2 O H 2 SO 4 catalyst Condensation Reaction

11.4 Functional Group Chemistry Aldehydes and ketones contain the carbonyl ( ) functional group. O C R C H O aldehydes have the general formulaR C R’ O ketones have the general formulaH C H O H C O CH 3 C O H3CH3C formaldehydeacetaldehydeacetone

11.4 Functional Group Chemistry Carboxylic acids contain the carboxyl ( -COOH ) functional group.

11.4 Functional Group Chemistry Esters have the general formula R’COOR, where R is a hydrocarbon group. CH 3 COOH + HOCH 2 CH 3 CH 3 C O CH 2 CH 3 + H 2 O O ethyl acetate

11.4 Functional Group Chemistry Amines are organic bases with the general formula R 3 N. CH 3 NH 2 + H 2 O RNH OH - CH 3 CH 2 NH 2 + HCl CH 3 CH 2 NH 3 + Cl -

11.4

Chemistry In Action: The Petroleum Industry Crude Oil

Out of Crude Oil