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

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

3. 11.1 Common Elements in Organic Compounds

4. 11.1 Classification of Hydrocarbons

5. 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

6. 11.2 Structural isomers are molecules that have the same molecular formula but different structures

7. 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

8. 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 3 1234567 4-methylheptane 2.An alkane less one hydrogen atom is an alkyl group. CH 4 CH 3 methane methyl

9. 11.2 Alkane Nomenclature

10. 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 3 12345 2-methylpentane CH 3 CH 2 CHCH 3 12345 4-methylpentane

11. 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 123456 2,3-dimethylhexane CH 3 CHCCH 2 CH 3 12 3 456 3,3-dimethylhexane

12. 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

13. What is the IUPAC name of the following compound? 11.2 1234567 8 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? 123456 CH 3 CHCH 2 CHCH 2 CH 3 C3H7C3H7

14. 11.2 It is 3,5-dimethyloctane! 123456 CH 3 CHCH 2 CHCH 2 CH 3 C3H7C3H7 2-propyl-4-methylhexane? CH 3 CHCH 2 CHCH 2 CH 3 123456 CH 2 6 5 4 3 21 7 8

15. 11.2 Alkane Reactions CH 4 (g) + 2O 2 (g) CO 2 (g) + 2H 2 O (l)  H 0 = -890.4 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

16. 11.2 achiralchiral Enantiomer or Optical isomers 거울상 이성질체

17. 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,…

18. Cycloalkanes 11.2

19. 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

20. Cis-Trans Isomerization in the Vision Process 11.2

21. 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

22. 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%)

23. 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

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

25. 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

26. 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)

27. 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)

28. Chemistry In Action: Ice That Burns

29. 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

30. 11.3 Aromatic Compound Nomenclature CH 2 CH 3 ethylbenzene Cl chlorobenzene NH 2 aminobenzene NO 2 nitrobenzene 1 2 3 4 5 6 Br 1,2-dibromobenzene Br 1,3-dibromobenzene

31. 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

32. 11.3 Polycyclic Aromatic Hydrocarbons

33. 11.4 Functional Group Chemistry Alcohols contain the hydroxyl functional group and have the general formula R-OH.

34. 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

35. 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

36. 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

37. 11.4 Functional Group Chemistry Carboxylic acids contain the carboxyl ( -COOH ) functional group.

38. 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

39. 11.4 Functional Group Chemistry Amines are organic bases with the general formula R 3 N. CH 3 NH 2 + H 2 O RNH 3 + + OH - CH 3 CH 2 NH 2 + HCl CH 3 CH 2 NH 3 + Cl -

40. 11.4

41. Chemistry In Action: The Petroleum Industry Crude Oil

42. Out of Crude Oil