CHEM 1152 Survey of Chemistry II

1. CHEM 1152 Survey of Chemistry II

2. 2 What is Organic Chemistry??

3. 3 Vital Force Theory

4. 4 Discovery

5. 5 Present

6. 6 Organic vs. Inorganic Covalent bonding (nonpolar) Made of Carbon bonded to each other and other nonmetals Small attraction between molecules Ionic bonding Made of metals and nonmetals Strong attraction between molecules Water soluble

7. 7 Molecular Polarities

8. 8 Lewis Model of Bonding Nitrogen forms 3 covalent bonds and has one unshared electron pair .. . N . . Carbon forms 4 covalent bonds and lacks unshared electron pairs . . C . .

9. 9 Lewis Model of Bonding Hydrogen forms 1 covalent bond and lacks unshared electron pairs H . Oxygen forms 2 covalent bonds and has 2 unshared electron pairs .. . O . ..

10. 10 Lewis Model of Bonding Chlorine(and fluorine, bromine, and iodine as well) forms 1 covalent bond and has 3 unshared pairs of electrons .. . Cl: ..

11. 11 Classification of Compounds

12. 12 Saturated Hydrocarbons

13. 13 Alkanes Contain C and H only Contain single bonds C-C Have 4 bonds to every carbon (C) atom Are nonpolar Either acyclic or cyclic Formula CnH2n+2

14. 14 Complete Structural Formulas Show the bonds between each of the atoms H H ? ? H ? C ? H H C H ? ? H H CH4 In methane, CH4 the four valence electrons of carbon are shared with the single electrons of four hydrogen (H) atoms. Each pair of electrons is a single bond, which can be drawn as a line. When a structure is drawn to show each bond, it is called a complete structural formula.In methane, CH4 the four valence electrons of carbon are shared with the single electrons of four hydrogen (H) atoms. Each pair of electrons is a single bond, which can be drawn as a line. When a structure is drawn to show each bond, it is called a complete structural formula.

15. 15 Structural Formulas H H Expanded vs. Condensed H C C H CH3 CH3 H H H H H H C C C H CH3 CH2 CH3 H H H The complete structural formula for ethane shows the single bonds between two carbon atoms and six H atoms. The complete structural formula of propane shows the 3-carbon chain with single bonds to the attached H atoms. To write a condensed structural formula, the H atoms are written as a group next to their respective C atoms. The complete structural formula for ethane shows the single bonds between two carbon atoms and six H atoms. The complete structural formula of propane shows the 3-carbon chain with single bonds to the attached H atoms. To write a condensed structural formula, the H atoms are written as a group next to their respective C atoms.

16. 16 Nomenclature

17. 17 Nomenclature 1. Find the longest continuous chain (parent chain) and give it a name based on the number of carbons with the suffix -ane. 2. Number the parent chain to give the first substituent the smallest number. 3. Name and locate each group and use it as a prefix for the parent.

18. 18 Nomenclature When 2 or more substituents are identical, use such prefixes as di (for 2) , tri (for 3), tetra (for 4), penta (for 5), etc. in addition to the location number. When multiple kinds of substituents are present on the parent, number each group and list the names alphabetically. 6. Follow the punctuation rules: a. separate numbers from each other by commas, b. separate numbers from letters by hyphens, c. do not use a hyphen or space between the last substituent and the parent.

19. 19 Nomenclature

20. 20 IUPAC Names Name # carbons Structural Formula Methane 1 CH4 Ethane 2 CH3CH3 Propane 3 CH3CH2CH3 Butane 4 CH3CH2CH2CH3 Pentane 5 CH3CH2CH2CH2CH3 The names of organic compounds are determined by the IUPAC rules (International Union of Pure and Applied Chemistry). The stem of the name states the number of carbon atoms in the carbon chain of the compounds. The suffix, in this case –ane, indicates the alkane family.The names of organic compounds are determined by the IUPAC rules (International Union of Pure and Applied Chemistry). The stem of the name states the number of carbon atoms in the carbon chain of the compounds. The suffix, in this case –ane, indicates the alkane family.

21. 21 IUPAC NAMES Name # carbons Structural Formula Hexane 6 CH3CH2CH2CH2CH2CH3 Heptane 7 CH3CH2CH2CH2CH2CH2CH3 Octane 8 CH3CH2CH2CH2CH2CH2CH2CH3 Nonane 9 CH3 CH2 CH2CH2CH2CH2CH2CH2CH3 Decane 10 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

22. 22 Nomenclature

23. 23 Nomenclature

24. 24 Learning Check Alk1 A. What is the condensed formula for H H H H H C C C C H H H H H B. What is its molecular formula? C. What is its name?

25. 25 Solution Alk1 A. CH3CH2CH2CH3 B. C4H10 C. butane

26. 26 Saturated Hydrocarbons Isomers Branched Alkanes Carbon Classification Branched Alkyl Groups Haloalkanes

27. 27 Isomers Same molecular formula (same number and types of atoms) Different arrangement of atoms Are different compounds with different properties Structural isomers are compounds that have the same molecular formula with different arrangements of the atoms.Structural isomers are compounds that have the same molecular formula with different arrangements of the atoms.

28. 28 Isomers

29. 29 Recognizing Isomers

30. 30 Examples of Isomers The formula C4H10 has two different structures CH3 CH3CH2CH2CH3 CH3CHCH3 Butane 2-methylpropane

31. 31 Learning Check Alk2 Write 3 isomers of C5H12 and name each.

32. 32 Solution Alk2 CH3CH2CH2CH2CH3 pentane CH3 CH3CHCH2CH3 2-methylbutane CH3 CH3CCH3 2,2-dimethylpropane CH3

33. 33 Branched Alkanes When one or more branches CH3 (substituents) are attached to a continuous carbon chain CH3CHCH3 methyl groups CH3 CH3 CH3CHCH2CHCH3 In the structural formula of an alkane, the alkyl group is typically attached vertically above or below the carbon chain.In the structural formula of an alkane, the alkyl group is typically attached vertically above or below the carbon chain.

34. 34 Naming Branched Alkanes CH3 methyl branch CH3CH2CH2CHCH2CH3 6 5 4 3 2 1 A branched-chain alkane is named by indicating the attached groups on the longest carbon chain. In this example, the longest carbon chain has 6 carbon atoms. A branched-chain alkane is named by indicating the attached groups on the longest carbon chain. In this example, the longest carbon chain has 6 carbon atoms.

35. 35 Naming Branched Alkanes CH3 methyl branch CH3CH2CH2CHCH2CH3 6 5 4 3 2 1 Count 3-Methylhexane on third C CH3 six carbon chain group The chain is numbered to give the side group or methyl group a location on carbon 3 in the chain. The chain is numbered to give the side group or methyl group a location on carbon 3 in the chain.

36. 36 Learning Check Alk3 A. CH3 CH3 CH3CHCH2CHCH3 B. CH3 CH3 CH3CH2CHCH2CCH2CH3 CH3

37. 37 Solution Alk3 A. CH3 CH3 CH3CHCH2CHCH3 2,4-dimethylpentane B. CH3 CH3 CH3CH2CHCH2CCH2CH3 CH3 3,3,5-trimethylheptane

38. 38 Learning Check Alk4 Write a condensed structure for A. 3,4-dimethylheptane B. 2,2-dimethyloctane

39. 39 Solution Alk4 A. 3,4-dimethylheptane CH3 CH3CH2CHCHCH2CH2CH3 CH3 2,2-dimethyloctane CH3 CH3CCH2CH2CH2CH2CH2CH3 CH3

40. 40 Carbon Classification CH3 CH3CH2CH3 CH3CHCH3 CH3 CH3CH2CH2CCH2CH3 CH3

41. 41 Branched Alkyl Groups Isopropyl Isobutyl sec-butyl tert-butyl

42. 42 Nomemclature of Complex Branched Alkyl Groups Find the longest alkyl chain in the complex substituent Number the chain starting with the carbon that is attached to the parent chain Number and name the substituents on the complex chain Use parentheses to separate this name from that of the parent

43. 43 Haloalkanes An alkane in which one or more H atoms is replaced with a halogen (F, Cl, Br, or I) CH3Br Bromomethane CH3CH2CH2CH2F 1-Fluorobutane CH3CH2CH2F 1- Chloropropane CH3CH2I 1- Iodoethane

44. 44 List other attached atoms or group in alphabetical order: Br = bromo, Cl = chloro Cl Br CH3CHCH2CHCH2CH2CH3 4-bromo-2-chloroheptane Substituents

45. 45 Learning Check Alk5 The name of this compound is: Cl CH3 CH3CH2CHCH2CHCH3 1) 2,4-dimethylhexane 2) 3-chloro-5-methylhexane 3) 4-chloro-2-methylhexane

46. 46 Solution Alk5 The name of this compound is: Cl CH3 CH3CH2CHCH2CHCH3 3) 4-chloro-2-methylhexane

47. 47 Haloalkanes as Anesthetics Halothane (Fluothane) F Cl F C C Br F H Fluothane is a haloalkane that is widely used as an anesthetic, which is a compound that decreases the ability of the nerve cells to conduct pain.

48. 48 Ozone Layer Ozone layer Stratosphere (6-30 miles Above Earth)

49. 49 ozone (O3 )layer absorbs most of the sun’s harmful radiation. CFCs - chlorofluorocarbons - are depleting that ozone layer. CFCs are used as Freons in refrigeration, air conditioning, and foam insulation. Their use in spray cans is no longer allowed. CFCs and the Ozone Layer

50. 50  CFCs In the stratosphere, the CFCs react with the high-energy UV radiation from the sun UV light CF2Cl2 CF2Cl? + Cl? Freon-12 free radical

51. 51 Effects of CFC’s To become stable, the Cl? acquires an electron from ozone O3 and produces ClO. Cl? + O3 ClO + O2 The presence of ClO in the atmosphere is an indicator of the disappearance of ozone.

52. 52 Impact of Loss of Ozone Layer According to the National Academy of Sciences, each 1% loss of ozone increases by 2% the amount of UV radiation reaching the earth. More UV radiation means more skin cancer and cataracts in humans, more intense photochemical smog, and lower crop yields.

53. 53 Saturated Hydrocarbons Line-Angle Drawing Cycloalkanes Cis-Trans Isomers Physical Properties Reactions

54. 54 Line –Angle Drawing

55. 55 Cyclic Hydrocarbons

56. 56 Cycloalkanes Cyclopropane CH2 CH2 CH2 Cyclobutane CH2 CH2 CH2 CH2 The is a group of alkanes that have a cyclic structure. These cycloalkanes contain a carbon chain that is in a ring. Each cycloalkane has a formula that is 2C less than the corresponding alkane. For example, propane is C3H8 whereas cyclopropane ic C3H6. Butane is C4H10 and cyclobutane is C4H10. The names of the cyclic structures use the prefix cyclo in from of the alkane name for the carbon chain.The is a group of alkanes that have a cyclic structure. These cycloalkanes contain a carbon chain that is in a ring. Each cycloalkane has a formula that is 2C less than the corresponding alkane. For example, propane is C3H8 whereas cyclopropane ic C3H6. Butane is C4H10 and cyclobutane is C4H10. The names of the cyclic structures use the prefix cyclo in from of the alkane name for the carbon chain.

57. 57 More Cycloalkanes Cyclopentane CH2 CH2 CH2 CH2 CH2 Cyclohexane CH2 CH2 CH2 CH2 CH2 CH2

58. 58 Naming Cycloalkanes with Substituents Number of Substituents Naming Rule 1 Substituent name precedes the cyclo- alkane name; no location number 2 Use alphabetical priority to determine which group is #1 and then number the ring such that the other group has as low a number as possible 3 or more Number the ring in the direction that gives the lowest numbers to the side groups; if two equal numbering schemes exist, use alphabetical priority to determine the correct naming sequence

59. 59 Cycloalkanes with Substituents

60. 60 Learning Check Alk6

61. 61 Solution Alk6

62. 62 Learning Check Alk7 Name the following:

63. 63 Solution Alk7 Name the following: bromocyclopentane 1,3-dichlorocyclohexane

64. 64 Cis –Trans Isomerism

65. 65 Cis –Trans Isomerism

66. 66 Cis –Trans Isomerism

67. 67 Physical Properties of Alkanes and Cycloalkanes

68. 68 Physical Properties

69. 69 Physical Properties

70. 70 Physical Properties

71. 71 Reactions of Alkanes Combustion alkane + O2 CO2 + H2O + heat

72. 72 Combustion In the Cell Metabolic oxidation is combustion C6H12 O6 + 6O2 6CO2 + 6H2O + 2,870 kJ glucose heat

73. 73 Learning Check Alk8 Complete the combustion reaction for C3H8 + O2 + Balance your equation

74. 74 Solution Alk8 Step 1 C3H8 + O2 CO2 + H2O Step 2 C3H8 + O2 3 CO2 + 4 H2O Step 3 C3H8 + 5 O2 3 CO2 + 4 H2O To balance the atoms in the formula C3H8, we place a coefficient of 3 in front of CO2 and a coefficient of 4 in front of H2O. The total O in the products is 10 O (6 O in 3CO2 and 4 O in 4 H2O). To balance the 10 O, a coefficient of 5 is placed in front of the O2.To balance the atoms in the formula C3H8, we place a coefficient of 3 in front of CO2 and a coefficient of 4 in front of H2O. The total O in the products is 10 O (6 O in 3CO2 and 4 O in 4 H2O). To balance the 10 O, a coefficient of 5 is placed in front of the O2.

75. 75 Learning Check Alk9 Complete and balance the reaction for the complete combustion of C7H16

76. 76 Solution Alk9 Step 1 C7H16 + O2 CO2 + H2O Step 2 C7H16 + O2 7 CO2 + 8 H2O Step 3 C7H16 + 11 O2 7 CO2 + 8 H2O The carbon has a subscript 7, which means we need to place a coefficient of 7 in front of CO2. The H subscript 16 is balanced by placing a coefficient of 8 in front of H2O. Finally, the total O of 22 ( 14 + 8) indicates that a coefficient of 11 in front of O2 will balance the O atoms.The carbon has a subscript 7, which means we need to place a coefficient of 7 in front of CO2. The H subscript 16 is balanced by placing a coefficient of 8 in front of H2O. Finally, the total O of 22 ( 14 + 8) indicates that a coefficient of 11 in front of O2 will balance the O atoms.

77. 77 Reactions of Alkanes Halogenation alkane + halogen light/heat haloalkane CH4 + Cl2 CH3Cl + HCl

78. 78 Reactions of Alkanes Halogenation Chlorination (Cl2) and Bromination (Br2) Fluorination (F2) and Iodination (I2) Reaction results in a mixture of products for alkanes but only 1 product forms with an unsubstituted cycloalkane.