1. Organic Chemistry 유기화학 Chapter 11 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Things to study 11.1 Classes of organic compounds 11.2 Aliphatic hydrocarbons 11.3 Aromatic hydrocarbons 11.4 Chemistry of functional groups 11.5 Chiality – The Handedness of Molecules

2. 11.1 Common Elements in Organic Compounds *Organic compounds ( 유기화합물 ): carbon compounds, 생물체에서 유래된 화합물 *Organic chemistry ( 유기화학 ): chemistry on carbon compounds *Functional groups ( 기능기, 작용기 ): 유기화합물의 화학특성을 좌우하는 원자들의 그룹 * 모든 유기화합물은 탄화수소 (hydrocarbons) 의 유도체 * Hydrocarbons 의 종류 - aliphatic hydrocarbons ( 지방족 탄화수소 ): 벤젠구조를 포함하지 않은 탄화수소 - aromatic hydrocarbons ( 방향족 탄화수소 ): 벤젠구조를 포함하는 탄화수소

3. 11.1 Classification of Hydrocarbons 탄화수소 지방족 방향족 알칸시클로알칸알켄알킨 단일결합만 존재 선형 단일결합만 존재 환형 이중결합 존재삼중결합 존재 암기

4. 11.2 Alkanes ( 알칸 ) Alkanes have the general formula C n H 2n+2 where n = 1,2,3,… only single covalent bonds 단일결합만 존재  포화탄화수소 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 암기

5. 11.2 Structural isomers ( 구조이성질체 ) are molecules that have the same molecular formula but different structures

6. How many structural isomers does pentane, C 5 H 12, have? 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 Example 11.1 질문 : 어떤 것이 분자간 인력 더 클까 ? 어떤 것이 bp 가 가장 높을까 ?

7. 11.2 Alkane Nomenclature ( 알켄 명명법 ) 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 긴 사슬을 읽는다

8. 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. 짧은 쪽부터 번호 부여 CH 3 CHCH 2 CH 3 12345 2-methylpentane CH 3 CH 2 CHCH 3 12345 4-methylpentane

9. 11.2 Alkane Nomenclature 4.Use prefixes di- (2 개 ), tri- (3 개 ), tetra- (4 개 ), 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

10. 11.2 Alkane Nomenclature 5.Use previous rules for other types of substituents( 치환기 ). 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

11. 11.2 What is the IUPAC name of the following compound? 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 C2H5C2H5 Example 11.2 유사문제 Practice Exercise (Example 11.3 밑의 연습 ) 유사문제

12. 11.2 Alkane Reactions CH 4 (g) + 2O 2 (g) CO 2 (g) + 2H 2 O (l)  H 0 = -890.4 kJ Combustion ( 연소 ) Halogenation ( 할로겐화 ) 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 Free radical ( 자유 라디칼 )

13. 11.2 Cycloalkanes ( 시클로알칸 ) Alkanes whose carbon atoms are joined in rings are called cycloalkanes. They have the general formula C n H 2n where n = 3,4,… 단일결합만 존재, 환형

14. Cycloalkanes 11.2

15. Alkenes ( 알켄 ) = Olefines 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 이중결합 존재 이중결합 가까운 쪽이 1 번

16. 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 Ethylene: 화학산업의 쌀

17. 11.2 Alkynes ( 알킨 ) 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) 3 중결합 존재

18. 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)

19. Chemistry In Action: Ice That Burns

20. 11.3 C C C CC C H H H H H H C C C CC C H H H H H H Aromatic Hydrocarbons ( 방향족 탄화수소 ) 벤젠구조 포함

21. 11.3 Aromatic Compound Nomenclature CH 2 CH 3 ethylbenzene Cl chlorobenzene NH 2 benzene aminobenzene NO 2 nitrobenzene 1 2 3 4 5 6 Br 1,2-dibromobenzene Br 1,3-dibromobenzene

22. 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

23. 11.3 Polycyclic Aromatic Hydrocarbons (PAH)

24. 11.4 Functional Group Chemistry Alcohols contain the hydroxyl functional group and have the general formula R-OH.

25. 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 acetaldehyde

26. 11.4 Functional Group Chemistry Ethers have the general formula R-O-R’. ( 에테르  이써 ) CH 3 OH + HOCH 3 CH 3 OCH 3 + H 2 O H 2 SO 4 catalyst Condensation Reaction

27. 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

28. 11.4 Functional Group Chemistry Carboxylic acids contain the carboxyl ( -COOH ) functional group.

29. 11.4 Functional Group Chemistry Esters have the general formula R’-COO-R, 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

30. 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 - 보통 R-NH 2

31. 11.4 암기

32. 11.5 Achiral ( 비키랄 )Chiral ( 키랄 ) 알칸의 거울상 이성질체 (optical isomers)

33. Chemistry In Action: The Petroleum Industry Crude Oil

34. Home Works for Chapter 11 1. 교과서 요약 읽기  제출 안 함 2. 예제 문제 풀기  제출 3. 교과서 연습문제  제출 14, 16, 22, 26, 32, 36, 42, 46 (8 문제 ) 4. 용어정리  제출 aliphatic hydrocarbons, alkane, alkene, alkyne, aromatic hydrocarbon cycloalkane, ester, ether, ketone, structural isomer, optical isomer 5.Multiple Choice Quiz  제출 안 함 6.11 장에 나와 있는 “ 유기화합물 구조 vs. 이름 ” 요약 및 암기 ## 시험은 대부분 (70% 이상 ) 숙제에서 출제함. ##