1. Timberlake LecturePLUS1 Alkanes and Aromatic Hydrocarbons Organic Compounds Bonding in Hydrocarbons Naming Alkanes Properties of Alkanes

2. Timberlake LecturePLUS2 “ The most important hypothesis in all of biology…is that everything that animals do, atoms do. In other words, there is nothing that living things do that cannot be understood from the point of view that they are made of atoms acting according to the laws of physics.” Richard Feynman (1918-1988)

3. Timberlake LecturePLUS3 Organic Compounds  Contain carbon  Have covalent bonds  Have low melting points  Have low boiling points  Burn in air (oxygen)  Are soluble in nonpolar solvents  Form large molecules

4. Timberlake LecturePLUS4 Alkanes Contain C and H only Contain single bonds C-C Have 4 bonds to every carbon (C) atom Are nonpolar

5. Timberlake LecturePLUS5 Complete Structural Formulas Show the bonds between each of the atoms H H  H  C  HH C H  H H CH 4, methane

6. Timberlake LecturePLUS6 More Alkanes H HCondensed Structural Formulas H C C HCH 3 CH 3 H HEthane H H H H C C C HCH 3 CH 2 CH 3 H H H Propane

7. Timberlake LecturePLUS7 IUPAC Names Name# carbons Structural Formula Methane1CH 4 Ethane2CH 3 CH 3 Propane3CH 3 CH 2 CH 3 Butane4CH 3 CH 2 CH 2 CH 3 Pentane5CH 3 CH 2 CH 2 CH 2 CH 3

8. Timberlake LecturePLUS8 IUPAC NAMES Name # carbons Structural Formula Hexane 6 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 Heptane 7 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Octane 8 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Nonane 9 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Decane 10 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3

9. Timberlake LecturePLUS9 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?

10. Timberlake LecturePLUS10 Solution Alk1 A.CH 3 CH 2 CH 2 CH 3 B. C 4 H 10 C.butane

11. Timberlake LecturePLUS11 Reactions of Alkanes Combustion alkane + O 2 CO 2 + H 2 O + heat

12. Timberlake LecturePLUS12 Combustion In the Cell Metabolic oxidation is combustion C 6 H 12 O 6 + 6O 2 6CO 2 + 6H 2 O + heat glucose

13. Timberlake LecturePLUS13 Learning Check Alk2 Complete the combustion reaction for C 3 H 8 + O 2 + Balance your equation

14. Timberlake LecturePLUS14 Solution Alk2 Step 1 C 3 H 8 + O 2 CO 2 + H 2 O Step 2 C 3 H 8 + O 2 3 CO 2 + 4 H 2 O Step 3 C 3 H 8 + 5 O 2 3 CO 2 + 4 H 2 O

15. Timberlake LecturePLUS15 Learning Check Alk3 Complete and balance the reaction for the complete combustion of C 7 H 16

16. Timberlake LecturePLUS16 Solution Alk3 Step 1 C 7 H 16 + O 2 CO 2 + H 2 O Step 2 C 7 H 16 + O 2 7 CO 2 + 8 H 2 O Step 3 C 7 H 16 + 11 O 2 7 CO 2 + 8 H 2 O

17. Timberlake LecturePLUS17 Chapter 11 Haloalkanes, Alkenes, and Alkynes Alkenes and Alkynes Geometric Isomers of Alkenes Addition Reactions

18. Timberlake LecturePLUS18 Saturated and Unsaturated Compounds Saturated compounds (alkanes) have the maximum number of hydrogen atoms attached to each carbon atom Unsaturated compounds have fewer hydrogen atoms attached to the carbon chain than alkanes Unsaturated compounds contain double or triple bonds

19. Timberlake LecturePLUS19 Alkenes  Carbon-carbon double bonds  Names end in -ene H 2 C=CH 2 ethene (ethylene) H 2 C=CH-CH 3 propene (propylene) cyclohexene

20. Timberlake LecturePLUS20 Alkynes  Carbon-carbon triple bonds  Names end in -yne HC  CHethyne(acetylene) HC  C-CH 3 propyne

21. Timberlake LecturePLUS21 Naming Alkenes and Alkynes When the carbon chain has 4 or more C atoms, number the chain to give the lowest number to the double or triple bond. 1 2 3 4 CH 2 =CHCH 2 CH 3 1-butene CH 3 CH=CHCH 3 2-butene CH 3 CH  CHCH 3 2-butyne

22. Timberlake LecturePLUS22 Learning Check HA3 Write the IUPAC name for each of the following unsaturated compounds: A.CH 3 CH 2 C  CCH 3 CH 3 B. CH 3 C=CHCH 3 C.

23. Timberlake LecturePLUS23 Solutions HA3 Write the IUPAC name for each of the following unsaturated compounds: A.CH 3 CH 2 CH=CHCH 3 2-pentyne CH 3 B. CH 3 C=CHCH 3 C. 2-methyl-2-butene 3-methylcyclopentene

24. Timberlake LecturePLUS24 Cis and Trans Isomers  Double bond is fixed  Cis/trans Isomers are possible CH 3 CH 3 CH 3 CH = CH CH = CH cis trans CH 3

25. Timberlake LecturePLUS25 Hydrogenation Adds a hydrogen atom to each carbon atom of a double bond H H H H Ni H–C=C–H + H 2 H–C–C–H H H ethene ethane

26. Timberlake LecturePLUS26 Products of Hydrogenation Adding H 2 to vegetable oils produces compounds with higher melting points Margarines Soft margarines Shortenings (solid)

27. Timberlake LecturePLUS27 Learning Check HA4 What is the product of adding H 2 (Ni catalyst) to 1-butene?

28. Timberlake LecturePLUS28 Solution HA4 What is the product of adding H 2 (Ni catalyst) to 1-butene? Ni CH 2 =CHCH 2 CH 3 + H 2 CH 3 CH 2 CH 2 CH 3

29. Timberlake LecturePLUS29 Adding Halogens Halogens also add to the double bond of an alkene. H 2 C  CH 2 + Cl 2

30. Timberlake LecturePLUS30 Learning Check HA5 Write the product of the following addition reactions: CH 3 CH=CHCH 3 + H 2

31. Timberlake LecturePLUS31 Solution HA5 Write the product of the following addition reactions: CH 3 CH=CHCH 3 + H 2 CH 3 CH 2 CH 2 CH 3

32. Timberlake LecturePLUS32 Unsaturated Fatty Acids Fatty acids in vegetable oils are omega-6 acids (the first double bond occurs at carbon 6 counting from the methyl group) A common omega-6 acid is linoleic acid CH 3 CH 2 CH 2 CH 2 CH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH 6 linoleic acid, a fatty acid

33. Timberlake LecturePLUS33 Trans Fats  In vegetable oils, the unsaturated fats usually contain cis double bonds.  During hydrogenation, some cis double bonds are converted to trans double bonds (more stable) causing a change in the fatty acid structure  If a label states “partially” or “fully hydrogenated”, the fats contain trans fatty acids.

34. Timberlake LecturePLUS34 Trans Fats  In the US, it is estimated that 2-4% of our total Calories is in the form of trans fatty acid.  trans fatty acids behave like saturated fatty acids in the body.  Several studies reported that trans fatty acids raise LDL-cholesterol. Some studies also report that trans fatty acid lower HDL- cholesterol  The trans fatty acids controversy will continue to be debated.

35. Timberlake LecturePLUS35 Fats and Atheroschlerosis Inuit people of Alaska have a high fat diet and high blood cholesterol levels, but a very low occurrence of atherosclerosis and heart attacks. Fat in the Intuit diet was primarily from fish such as salmon, tuna and herring rather than from land animals (as in the American diet).

36. Timberlake LecturePLUS36 Omega-3 Fatty Acids Fatty acids in the fish oils are mostly the omega-3 type (first double bond occurs at the third carbon counting from the methyl group). linolenic acid 18 carbon atoms CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH  eicosapentaenoic acid (EPA) 20 carbon atoms CH 3 CH 2 (CH=CHCH 2 ) 5 (CH 2 ) 2 COOH

37. Timberlake LecturePLUS37 Atherosclerosis Plaques of cholesterol adhere to the walls of the blood vessels Blood pressure rises as blood squeezes through smaller blood vessels Blood clots may form Omega-3 fatty acids decrease the “sticking” of blood platelets (fewer blood clots) Omega-3 fatty acids can increase bleeding time

38. Timberlake LecturePLUS38 Learning Check HA6 (1) Ture or (2) False A. ____ There are more unsaturated fats in vegetable oils. B. ____ Vegetable oils have more omega-3 oils than found in fish. C. ____ Hydrogenation of oils converts some cis-double bonds to trans- double bonds. D. ____ Animal fats have more saturated fats.

39. Timberlake LecturePLUS39 Solution HA6 (1) True or (2) False A. _T__ There are more unsaturated fats in vegetable oils. B. _F__ Vegetable oils have more omega-3 oils than found in fish. C. _T__ Hydrogenation of oils converts some cis-double bonds to trans- double bonds. D. _T__ Animal fats have more saturated fats.

40. Timberlake LecturePLUS40 Chapter 10 Alkanes and Aromatic Hydrocarbons Branched Alkanes Structural Formulas

41. Timberlake LecturePLUS41 Alkyl Groups Branches on carbon chains H H C CH 3 methyl H H H H C C CH 3 CH 2 ethyl H H

42. Timberlake LecturePLUS42 Branched Alkanes CH 3 CH 3 CHCH 3 methyl groups CH 3 CH 3 CH 3 CHCH 2 CHCH 3

43. Timberlake LecturePLUS43 Naming Branched Alkanes CH 3 methyl branch CH 3 CH 2 CH 2 CHCH 2 CH 3 6 5 4 3 2 1Count

44. Timberlake LecturePLUS44 Naming Branched Alkanes CH 3 methyl branch CH 3 CH 2 CH 2 CHCH 2 CH 3 6 5 4 3 2 1Count 3-Methylhexane on third C CH 3 six carbon chain group

45. Timberlake LecturePLUS45 Naming Summary 1. Count the C’s in the longest chain 2. Name each attached group 3 Count the longest carbon chain to give the first attached group the smallest number 4. Name and locate each group

46. Timberlake LecturePLUS46 Learning Check Alk4 A. CH 3 CH 3 CH 3 CHCH 2 CHCH 3 B. CH 3 CH 3 CH 3 CH 2 CHCH 2 CCH 2 CH 3 CH 3

47. Timberlake LecturePLUS47 Solution Alk4 A. CH 3 CH 3 CH 3 CHCH 2 CHCH 3 2,4-dimethylpentane B. CH 3 CH 3 CH 3 CH 2 CHCH 2 CCH 2 CH 3 CH 3 3,3,5-trimethylheptane

48. Timberlake LecturePLUS48 Learning Check Alk5 Write a condensed structure for A. 3,4-dimethylheptane B. 2,2-dimethyloctane

49. Timberlake LecturePLUS49 Solution Alk5 A. 3,4-dimethylheptane CH 3 CH 3 CH 2 CHCHCH 2 CH 2 CH 3 CH 3 B.2,2-dimethyloctane CH 3 CH 3 CCH 2 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3

50. Timberlake LecturePLUS50 Learning Check Alk6 Write 3 isomers of C 5 H 12 and name each.

51. Timberlake LecturePLUS51 Solution Alk6 CH 3 CH 2 CH 2 CH 2 CH 3 pentane CH 3 CH 3 CHCH 2 CH 3 2-methylbutane CH 3 CH 3 CCH 3 2,2-dimethylpropane CH 3

52. Timberlake LecturePLUS52 Isomers  Same molecular formula  Same number and types of atoms  Different arrangement of atoms

53. Timberlake LecturePLUS53 Examples of Isomers The formula C 4 H 10 has two different structures CH 3 CH 3 CH 2 CH 2 CH 3 CH 3 CHCH 3 Butane 2-methylpropane When a CH 3 is is used to form a branch, it makes a new isomer of C 4 H 10.

54. Timberlake LecturePLUS54 Learning Check Alk7 Write the structural formulas of 3 isomers that have the formula C 5 H 12. Name each.

55. Timberlake LecturePLUS55 Solution Alk7 Write the structural formulas of 3 isomers that have the formula C 5 H 12. Name each. CH 3 CH 2 CH 2 CH 2 CH 3 pentane CH 3 CH 3 CH 3 CHCH 2 CH 3 CH 3 CCH 3 CH 3 2-methylbutane 2,2-dimethylpropane

56. Timberlake LecturePLUS56 Chapter 10 Alkanes and Aromatic Hydrocarbons Cycloalkanes Aromatic Hydrocarbons

57. Timberlake LecturePLUS57 Cycloalkanes Cyclopropane CH 2 CH 2 CH 2 Cyclobutane CH 2 CH 2 CH 2

58. Timberlake LecturePLUS58 More Cycloalkanes Cyclopentane CH 2 CH 2 CH 2 CH 2 Cyclohexane CH 2

59. Timberlake LecturePLUS59 Naming Cycloalkanes with Side Groups Number of Naming side groups OneSide group name goes in front of the cycloalkane name. TwoNumber the ring in the direction that gives the lowest numbers to the side groups.

60. Timberlake LecturePLUS60 Cycloalkanes with Side Groups

61. Timberlake LecturePLUS61 Learning Check Alk8

62. Timberlake LecturePLUS62 Solution Alk8

63. Timberlake LecturePLUS63 Aromatic Compounds and Benzene Aromatic compounds contain benzene. Benzene, C 6 H 6, is represented as a six carbon ring with 3 double bonds. Two possible can be drawn to show benzene in this form.

64. Timberlake LecturePLUS64 Benzene Structure The structures for benzene can also be written as a single structure where the alternating double bonds are written as a circle within the ring. Benzene structure

65. Timberlake LecturePLUS65 Aromatic Compounds in Nature and Health Many aromatic compounds are common in nature and in medicine.

66. Timberlake LecturePLUS66 Naming Aromatic Compounds Aromatic compounds are named with benzene as the parent chain. One side group is named in front of the name benzene. methylbenzenechlorobenzene (toluene)

67. Timberlake LecturePLUS67 Naming Aromatic Compounds When two groups are attached to benzene, the ring is numbered to give the lower numbers to the side groups. The prefixes ortho (1,2), meta (1,3-) and para (1,4-) are also used.

68. Timberlake LecturePLUS68 Some Common Names Some substituted benzene rings also use a common name. Then naming with additional more side groups uses the ortho-, meta-, para- system.

69. Timberlake LecturePLUS69 Learning Check Alk9 Select the names for each structure: 1. Chlorocyclohexane 2. Chlorobenzene 3. 1-chlorobenzene 1. Meta-methyltoluene 2. Meta-dimethylbenzene 3. 1,3-dimethylbenzene

70. Timberlake LecturePLUS70 Solution Alk9 Select the names for each structure: 2. Chlorobenzene 1. Meta-methyltoluene 2. Meta-dimethylbenzene 3. 1,3-dimethylbenzene

71. Timberlake LecturePLUS71 Learning Check Alk10 Write the structural formulas for each of the following: A. 1,3-dichlorobenzene B. Ortho-chlorotoluene

72. Timberlake LecturePLUS72 Solution Alk10 Write the structural formulas for each of the following: A. 1,3-dichlorobenzene B. Ortho-chlorotoluene

73. Timberlake LecturePLUS73 Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones Alcohols, Phenols, and Thiols Ethers Reactions of Alcohols

74. Timberlake LecturePLUS74 Compounds with Oxygen Atoms Alcohols-OH hydroxyl CH 3 -OH CH 3 CH 2 -OH Phenols Ethers -O- CH 3 -O-CH 3

75. Timberlake LecturePLUS75 Learning Check Al1 Classify each as an alcohol (1), phenol (2), or an ether (3): A. _____ CH 3 CH 2 -O-CH 3 C. _____ CH 3 CH 2 OH B. _____

76. Timberlake LecturePLUS76 Solution Al 1 Classify each as an alcohol (1), phenol (2), or an ether (3): A. __3__ CH 3 CH 2 -O-CH 3 C. __1__ CH 3 CH 2 OH B. _ 2__

77. Timberlake LecturePLUS77 Naming Alcohols A carbon compound that contain -OH (hydroxyl) group In IUPAC name, the -e in alkane name is replaced with -ol. CH 4 methane CH 3 OH methanol (methyl alcohol) CH 3 CH 3 ethane CH 3 CH 2 OH ethanol (ethyl alcohol )

78. Timberlake LecturePLUS78 Ethanol CH 3 CH 2 OH Acts as a depressant Kills or disables more people than any other drug 12-15 mg/dL ethanol metabolized by a social drinkers in one hour 30 mg/dL ethanol metabolized by an alcoholic in one hour.

79. Timberlake LecturePLUS79 Alcohol in Some Products % EthanolProduct 50%Whiskey, rum, brandy 40%Flavoring extracts 15-25%Listerine, Nyquil, Scope 12%Wine, Dristan, Cepacol 3-9%Beer, Lavoris

80. Timberlake LecturePLUS80 More Names of Alcohols IUPAC names for longer chains number the chain from the end nearest the -OH group. CH 3 CH 2 CH 2 OH1-propanol OH CH 3 CHCH 3 2-propanol CH 3 OH CH 3 CHCH 2 CH 2 CHCH 3 5-methyl-2-hexanol

81. Timberlake LecturePLUS81 Some Typical Alcohols OH “rubbing alcohol”CH 3 CHCH 3 2-propanol (isopropyl alcohol) antifreeze HO-CH 2 -CH 2 -OH 1,2-ethanediol (ethylene glycol) OH glycerolHO-CH 2 -CH-CH 2 OH Anti-freeze

82. Timberlake LecturePLUS82 Learning Check Al 2 Name the following alcohols: A. OH CH 3 CHCHCH 2 CH 3 CH 3 OH B.

83. Timberlake LecturePLUS83 Solution Al 2 Name the following alcohols: A. OH 3-methyl-2-pentanol CH 3 CHCHCH 2 CH 3 CH 3 OH B. cyclobutanol

84. Timberlake LecturePLUS84 Phenols IUPAC name for benzene with a hydroxyl group Many are used as antiseptics and disinfectants

85. Timberlake LecturePLUS85 Phenols in Medicine

86. Timberlake LecturePLUS86 Thiols Contain the functional group -SH Named by adding thiol to the name of the longest carbon chain Number the -SH group in longer chains CH 3 -SH methanethiol CH 3 -CH 2 SH ethanethiol SH CH 3 -CH-CH 3 2-propanethiol

87. Timberlake LecturePLUS87 Thiols Many thiols have disagreeable odors Used to detect gas leak Found in onions, oysters, garlic and oysters Onions CH 3 CH 2 CH 2 -SH 1-propanethiol Garlic CH 2 = CHCH 2 -SH 2-propene-1-thiol Skunk spray CH 3 trans-2-butene-1-thiol CH = CH CH 2 SH

88. Timberlake LecturePLUS88 Ethers Contain an -O- between two carbon groups Simple ethers named from -yl names of the attached groups and adding ether. CH 3 -O-CH 3 dimethyl ether CH 3 -O-CH 2 CH 3 ethyl methyl ether

89. Timberlake LecturePLUS89 Ethers as Anesthetics Anesthetics inhibit pain signals to the brain CH 3 CH 2 -O-CH 2 CH 3 used for over a century (Morton, 1846) Causes nausea and is highly flammable 1960s developed nonflammable anesthetics Cl F F Cl F HH-C-C-O-C-H F F F H F H Ethane(enflurane) Penthrane

90. Timberlake LecturePLUS90 MTBE Methyl tert-butyl ether CH 3 CH 3 -O-C-CH 3 CH 3 Second in production or organic chemicals Additive to improve gasoline performance Use in question with discovery of contaminated water supplies

91. Timberlake LecturePLUS91 Reactions of Alcohols Combustion CH 3 OH + 2O 2 CO 2 + 2H 2 O + Heat Dehydration H OH H +, heat H-C-C-H H-C=C-H + H 2 O H H alcohol alkene

92. Timberlake LecturePLUS92 Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones Aldehydes and Ketones

93. Timberlake LecturePLUS93 Aldehydes and Ketones In an aldehyde, an H atom is attached to a carbonyl group Ocarbonyl group  CH 3 -C-H In a ketone, two carbon groups are attached to a carbonyl group Ocarbonyl group  CH 3 -C-CH 3

94. Timberlake LecturePLUS94 Naming Aldehydes IUPAC Replace the -e in the alkane name -al Common Add aldehyde to the prefixes form (1C), acet (2C), propion(3), and butry(4C) O O O    H-C-H CH 3 -C-HCH 3 CH 2 C-H methanal ethanal propanal (formaldehyde) (acetaldehyde) (propionaldehyde)

95. Timberlake LecturePLUS95 Aldehydes as Flavorings

96. Timberlake LecturePLUS96 Glucose is an aldehyde

97. Timberlake LecturePLUS97 Naming Ketones In the IUPAC name, the -e in the alkane name is replaced with -one In the common name, add the word ketone after naming the alkyl groups attached to the carbonyl group O  CH 3 -C-CH 3 CH 3 -C-CH 2 -CH 3 Propanone 2-Butanone (Dimethyl ketone) (Ethyl methyl ketone)

98. Timberlake LecturePLUS98 Ketones O O  Butter flavorCH 3 -C-C-CH 3 butanedione O  Clove flavorCH 3 -C-CH 2 CH 2 CH 2 CH 2 CH 3 2-heptanone

99. Timberlake LecturePLUS99 Fructose is a Ketone

100. Timberlake LecturePLUS100 Ketones as Hormones

101. Timberlake LecturePLUS101 Learning Check AK 1 Classify each as an aldehyde (1), ketone (2) or neither(3). O  A. CH 3 CH 2 CCH 3 B. CH 3 -O-CH 3 CH 3 O  C. CH 3 -C-CH 2 CHD. CH 3

102. Timberlake LecturePLUS102 Solution AK 1 Classify each as an aldehyde (1), ketone (2) or neither(3). O  A. CH 3 CH 2 CCH 3 2 B. CH 3 -O-CH 3 3 CH 3 O  C. CH 3 -C-CH 2 CH 1 D. 2 CH 3

103. Timberlake LecturePLUS103 Learning Check AK 2 Name the following O  A. CH 3 CH 2 CCH 3 B. CH 3 O  C. CH 3 -C-CH 2 CH CH 3

104. Timberlake LecturePLUS104 Solution AK 2 O  A. CH 3 CH 2 CCH 3 B. 2-butanone (ethyl methyl ketone) CH 3 O  C. CH 3 -C-CH 2 CH cyclohexanone CH 3 2,2-dimethylbutanal

105. Timberlake LecturePLUS105 Learning Check AK 3 Draw the structural formulas for each: A. 3-Methylpentanal B. 2,3-Dichloropropanal C. 3-Methyl-2-butanone

106. Timberlake LecturePLUS106 Solution AK 3 Draw the structural formulas for each: CH 3 O  A. 3-MethylpentanalCH 3 CHCHCH 2 CH Br O  B. 2,3-Dichloropropanal Br-CH 2 CHCH O  C. 3-Methyl-2-butanoneCH 3 CHCCH 3 CH 3