1. Organic Chemistry Chemistry of Carbon Compounds

2. Why so many C compounds? covalentlycarbon atoms have the unique ability to covalently bond with other carbon atoms in chains, rings, and networks

3. Lewis Diagram of C C carbon has 4 unpaired electrons so it can form 4 covalent bonds

4. Bonding Capacity H can form only 1 bond halogens (F, Cl, Br, I) form only 1 bond O and S form 2 bonds N and P form 3 bonds

5. Molecular Formulas show kind & # of atoms CH 3 OH CH 3 Cl Structural Formulas show kind & # of atoms show bond type (single (–), double (=) or triple (  )) show approximate shapes of molecules H H–C–H H

6. Condensed Structural Formula shows kind & # of atoms shows some structural information structural formula: H H H CCC H–C–C–C–H H H H CCC condensed structural formula: CH 3 CH 2 CH 3

7. Vocabulary

8. hydrocarbons hydrocarbons: organic compounds containing ONLY C and H atoms

9. Homologous Series Homologous Series: group of compounds with related structures & properties 3 series: alkanes, alkenes, alkynes each member of series: differs by addition of one repeating unit have fixed ratio of atoms

10. ALKANES C n H 2n+2 homologous series of saturated hydrocarbons saturated hydrocarbons s saturated hydrocarbons: organic compounds containing only single bonds

11. Alkanes (C n H 2n+2 ) C 3 H 8 H H H H–C–C–C–H H H H CH 3 CH 2 CH 3 molecular formula structural formula condensed structural formula

12. Alkanes: base unit CH 4 CH 3 CH 3 or C 2 H 6 CH 3 CH 2 CH 3 or C 3 H 8 CH 3 CH 2 CH 2 CH 3 or C 4 H 10 CH 3 CH 2 CH 2 CH 2 CH 3 or C 5 H 12 CH 2 repeating unit: CH 2

13. Naming straight-chain Alkanes name describes molecule so can draw it aneaneall alkanes have the suffix ane prefix: tells # of C ’ s

14. straight-chain alkane C 4 H 10 H H H–C–C–C–C–H H H butane

15. C 5 H 12 C 4 H 10 C3H8C3H8 C2H6C2H6 meth + ane CH 4 NameFormulaethanepropane butane pentane prefix# carbons meth1 eth2 prop3 but4 pent5 hex6 hept7 oct8 non9 dec10

16. Properties of Alkanes low reactivity –except readily undergo combustion (fuels) non-polar – don ’ t dissolve in water low mp & low bp - both increase with molecular mass –change systematically with # of C ’ s as # of C ’ s increases: mp/bp  molecules get heavier so more energy required to overcome IMF to change from liquid to gas phase high VP

17. A.low melting point B.high melting point C.soluble in polar solvents D.insoluble in nonpolar solvents Which property is generally characteristic of an organic compound? correct response = A

18. A.CH 4 B.C 2 H 6 C.C 3 H 8 D.C 4 H 10 Which of the following compounds has the highest boiling point? Correct answer = D non-polar coval cmpd: bp depends on strength of van der Waals interactions bp depends on strength of van der Waals interactions dispersion forces ↑ as size of molecule ↑ dispersion forces ↑ as size of molecule ↑

19. Branched-chain alkanes beginning with butane, C 4 H 10, there is more than 1 way to arrange the atoms H H–C–H H H–C–C–C–H H H H branched alkane: can ’ t link all the C ’ s without lifting pencil off paper more C atoms present the more isomers can have (more possible ways to arrange atoms)

20. Isomers compounds with same molecular formula but –different structures –different properties isomers have different chemical and physical properties

21. A note about isomers --- comparing 2 structural formulas: –if can superimpose structures, they are not isomers – they are same molecule! –if can rotate/flip one structural formulas on other, they are not isomers – they are same molecule!

22. ? same yes they are

23. ? same yes they are

24. ?same yes they are

25. ?same no they are not - these are isomers

26. Naming Branched-Chain Alkanes goal of name is to describe molecule so you can draw it

27. naming branched-chain alkanes longest continuous chain 1.find longest continuous chain of C atoms - bends don ’ t matter! 2.base name 2.base name: indicates # C ’ s in continuous chain 3.branchesfirst 3.branches named first “ yl ” to prefix name - count # C atoms & add “ yl ” to prefix name assign #’s to C on backbone 4.# location of branch: assign #’s to C on backbone - # C's so get lowest number for branch - every branch gets a # 5.more than one of same type of branch - use di, tri, etc.

28. H H–C–H H H–C–C–C–H H H H methyl branch has 1 carbon – methyl branch has to be at C-2 (only give branch # if necessary) methyl propane C 4 H 10 CH 3 CH(CH 3 )CH 3 propane longest continuous chain has 3 carbon atoms – propane

29. H H–C–H H H H H–C–C–C–C–H H H H H–C–H H longest continuous chain has hexane 6 C atoms: hexane methyl branch: 1 carbon = methyl 2 branch located at C-2 2-methyl hexane C 7 H 16 CH 3 CH(CH 3 )CH 2 CH 2 CH 2 CH 31 43 6 5 2

30. A note about branches If several branches with same # C atoms, can condense name a little 2-methyl, 3-methyl pentane becomes: –2,3-dimethyl pentane

31. H H – C – H H H H H – C – C – C – C – H H H H–C–H H–C–H H H longest continuous chain: 6 C’s = hexane branch: 1 C = methyl branch located at C-3 3-methyl hexane C 7 H 16 CH 3 CH 2 CH 2 CH(CH 3 )CH 2 CH 3 (right to left) CH 3 CH 2 CH(CH 3 )CH 2 CH 2 CH 3 (left to right) 1 234 5 6

32. Unsaturated hydrocarbons Unsaturated hydrocarbons: organic compounds containing one or more multiple (double/ triple) bonds

33. ALKENES C n H 2n homologous series of unsaturated hydrocarbons containing at least one double bond

34. Naming Alkenes name: prefix tells # of C ’ s in parent chain suffix: ene 1 st member is C 2 H 4: ethene H H H H C=C H H note: Alkenes with 4 or more C ’ s: need # to show which C double bond attached to

35. Naming Alkenes # C atoms in backbone & give double bond the lowest possible number H H H C=C–C–C–H H H C 4 H 8 CH 2 CHCH 2 CH 3 H H H H H–C–C=C–C–H H H C 4 H 8 CH 3 CHCHCH 3 1-butene 2-butene

36. Naming Branched-Chain Alkenes parent chain = longest chain that contains double bond position of double bond, not branches, determines numbering of backbone C’s give 1 st C in double bond lowest possible #

37. Properties of Alkenes non-polar – low solubility in H 2 O fairly low mp and low bp more reactive than alkanes : –double bond is weak point (site of reactivity)

38. ALKYNES C n H 2n-2 homologous series of unsaturated hydrocarbons containing at least one triple bond

39. Naming Alkynes name: prefix tells # of C ’ s –suffix: yne if necessary, number 1 st carbon atom where triple bond is found

40. H–C  C–HC 2 H 2 ethyne CHCH H H–C  C–C–H H H H H–C  C–C–C–H H H H–C–C  C–C–H H H C3H4C3H4 propyne CHCCH 3 C4H6C4H6 1-butyne CHCCH 2 CH 3 C4H6C4H6 2-butyne CH 3 CCCH 3

41. single bonds double bond triple bond - alkane - alkene - alkyne

42. 3 Homologous Series of HC ’ s -yneC n H 2n-2 Alkynes -eneC n H 2n Alkenes -aneC n H 2n+2 Alkanes EndingGeneral FormulaName of Series

43. A.C 2 H 2 B.C 2 H 4 C.C 6 H 6 D.C 6 H 14 Which compound belongs to the alkene series? correct answer = B alkenes follow the format C n H 2n A & C: C n H n, D: C n H 2n+2

44. A.C 2 H 2, C 2 H 4, C 2 H 6 B.C 2 H 4, C 3 H 4, C 4 H 8 C.C 2 H 4, C 2 H 6, C 3 H 6 D.C 2 H 4, C 3 H 6, C 4 H 8 In which group could the hydrocarbons all belong to the same homologous series? correct answer = D members of homologous series all have same relationship between atoms; every compound in set D fits formula C n H 2n

45. A.Ethene B.Ethyne C.Propene D.Propane Which of the following is a saturated hydrocarbon? correct answer = D all alkanes are saturated