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Organic Chemistry The Chemistry of Carbon. Table of Contents ‘Organic Chemistry’ Distilling Crude Oil Methane Ethane Propane Butane Pentane Alkanes Alcohols.

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Presentation on theme: "Organic Chemistry The Chemistry of Carbon. Table of Contents ‘Organic Chemistry’ Distilling Crude Oil Methane Ethane Propane Butane Pentane Alkanes Alcohols."— Presentation transcript:

1 Organic Chemistry The Chemistry of Carbon

2 Table of Contents ‘Organic Chemistry’ Distilling Crude Oil Methane Ethane Propane Butane Pentane Alkanes Alcohols Aldehydes and Ketones Ethers Functional Groups Alkenes & Alkynes Cycloalkanes Benzene Aromatic Hydrocarbons Carboxylic Acids Classes of Organic Compounds Chirality Polymers

3 World of Chemistry The Annenberg Film Series VIDEO ON DEMAND Organic chemistry is the study of carbon compounds. The versatility of carbon’s molecular structures provides the enormous range of properties of its compounds. Episode 21 Episode 21 – Carbon

4 Organic Chemistry Organic Chemistry: The chemistry of carbon and carbon-based compounds Chemistry in everyday life: Organic Chemistry in everyday life: Smells & tastes: fruits, chocolate, fish, mint Medications: aspirin, Tylenol, decongestants, sedatives Addictive substances: caffeine, nicotine, alcohol, narcotics Hormones/Neurotransmitters: adrenaline, epinephrine Food: carbohydrates, protein, fat Genetics: DNA, RNA Consumer products: plastics, nylon, rayon, polyester

5 Friedrich Wöhler Made the first organic compound from non-living substances. Shot down the Vital Force idea of organic substances.

6 Distilling Crude Oil

7 Fractional Distillation of Crude Oil Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 429

8

9 Energy Sources in United States Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 648 WoodCoalPetroleum / natural gasHydro and nuclear 1850 100 80 60 40 20 0 Percent 9 91 1900 21 71 5 3 1940 10 50 40 1980 20 70 10 1990 26 58 16

10 Distilling Crude Oil Separate fractions based on differences in boiling point.

11 American Petroleum Usage AMERICAN PETROLEUM USAGE 1 Barrel of Petroleum 93% Energy Marketplace 7% Materials Marketplace 42 Gallons of Crude Petroleum 36 Gallons Fuel 19 Gallons Gasoline (11 Gallons in 1920) At $3.00 per gallon $108. 00 7% (3 Gallons Crude) 100 Nylon Shirts At $20. 00 per shirt $2000. 00 Entrepreneurs: [Put an alligator on the shirt and make even more $$$$$] A Lesson in Economics (42 gallons) OR

12 London Dispersion Forces The temporary separations of charge that lead to the London force attractions are what attract one nonpolar molecule to its neighbors. Fritz London 1900-1954 London forces increase with the size of the molecules. Boiling points of simple hydrocarbons in degrees Kelvin C 5 H 12 C 4 H 10 C3H8C3H8 C2H6C2H6 CH 4 C 8 H 18 Molecular Weight 50 100 150 50 100 150 200 250 300 350 400 Temperature (Kelvin)

13 London Forces in Hydrocarbons Boiling points of simple hydrocarbons in degrees Kelvin C 5 H 12 C 4 H 10 C3H8C3H8 C2H6C2H6 CH 4 Simple hydrocarbons have only London dispersion forces as intermolecular forces C 8 H 18 Molecular Weight 50 100 150 50 100 150 200 250 300 350 400

14 Methane

15 molecular formula structural formula molecular shape ball-and-stick model CH 4 C H H HH H H H H 109.5 o C tetrahedron tetrahedral shape of methane C H H H H

16 Methane is Tetrahedral H H H H C

17 Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 634

18 Methane molecular formula structural formula molecular shape ball-and-stick model CH 4 C H H HH H H H H 109.5 o C

19 Methane Timberlake, Chemistry 7 th Edition, page 365 tetrahedron ball-and-stick model of methane tetrahedral shape of methane C H H H H

20 Ethane

21 H CCH H H H H Lewis structure of Ethane

22 Space filling model of Ethane Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635

23 Ball and Stick model of Ethane

24 Propane

25 Structure of Propane Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635

26 Butane

27 Structure of Butane Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635

28 Ball and Stick Models Ethane C 2 H 6 Propane C 3 H 8 Timberlake, Chemistry 7 th Edition, page 366

29 Hydrocarbons

30 First Ten Hydrocarbons Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane 1 2 3 4 5 6 7 8 9 10 CH 4 C 2 H 6 C 3 H 8 C 4 H 10 C 5 H 12 C 6 H 14 C 7 H 16 C 8 H 18 C 9 H 20 C 10 H 22 CH 4 CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Number of Carbon Atoms Molecular Formula Condensed Structural Formula

31 Hydrocarbons (alkanes)

32 First Ten Hydrocarbons Name Methane Ethane n-Propane n-Butane n-Pentane n-Hexane n-Heptane n-Octane n-Nonane n-Decane 1 2 3 4 5 6 7 8 9 10 CH 4 C 2 H 6 C 3 H 8 C 4 H 10 C 5 H 12 C 6 H 14 C 7 H 16 C 8 H 18 C 9 H 20 C 10 H 22 Number of Carbon Atoms Molecular Formula Melting Point, o C # of Isomers Boiling Point, o C -182.5 -183.2 -187.7 -138.3 -129.7 -95.3 -90.6 -56.8 -53.6 -29.7 -161.5 -88.6 -42.1 -0.5 36.1 68.7 98.4 125.7 150.8 174.0 0 2 3 5 9 18 35 75

33 Increasing mass and boiling point Copyright © 2007 Pearson Benjamin Cummings. All rights reserved. Methane 16 g/mol -161.5 o C Ethane 30 g/mol -88.6 o C Propane 44 g/mol -42.1 o C n-Butane 58 g/mol -0.5 o C

34 Increasing mass and boiling point Methane 16 g/mol -161.5 o C Ethane 30 g/mol -88.6 o C Propane 44 g/mol -42.1 o C n-Butane 58 g/mol -0.5 o C

35 Hydrocarbons 1 2 3 4 5 6 7 8 9 10 Number of Carbon Atoms Alkanes C n H 2n + 2 Alkynes C n H 2n-2 Alkenes C n H 2n _______ Ethyne Propyne Butyne Pentyne Hexyne Heptyne Octyne Nonyne Decyne ____ C 2 H 2 C 3 H 4 C 4 H 6 C 5 H 8 C 6 H 10 C 7 H 12 C 8 H 14 C 9 H 16 C 10 H 18 Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane CH 4 C 2 H 6 C 3 H 8 C 4 H 10 C 5 H 12 C 6 H 14 C 7 H 16 C 8 H 18 C 9 H 20 C 10 H 22 _______ Ethene Propene Butene Pentene Hexene Heptene Octene Nonene Decene ____ C 2 H 4 C 3 H 6 C 4 H 8 C 5 H 10 C 6 H 12 C 7 H 14 C 8 H 16 C 9 H 18 C 10 H 20

36 Isomers The fat dog shook himself, and then rolled over on the wet rug. The dog shook the fat rug, then rolled over and wet on himself. (These two statements use the same words... but have very different meanings.)

37 CH H H H Methane CH 4 H C CCC H H H H HHH H H Butane C 4 H 10 Butyl -C 4 H 9 Methyl -CH 3 CH H H ? R H C CCC H H H H HHH H R

38 Naming Alkanes 1. Find the longest continuous chain of carbon atoms in the molecule 2.Start numbering the chain at the carbon nearer the first branching point (the substituents should have the lowest numbers possible) 3. Name and number the substituents If there are two substituents attached to the same carbon, assign both of them the same number 4. Write out the name of the molecule List the substitutents names in alphabetical order if there are two identical substituents on the molecule, use the prefix di; if there are three identical substituents, use the prefix tri-; if there are four identical substituents, use the prefix tetra- (alphabetize the substituents by the main name of the substituent, not by any prefixes the substituents may have) Separate the substituents names with hyphens Tag the name of the parent chain onto the end of the substituent names

39 A Few Extra Rules to Follow Use commas to separate numbers Use hyphens to separate numbers from the substituent names Never name alkanes after drinking Don’t allow children to name alkanes unattended

40 Butane Butane Gas – lighters Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 107 H - C - C - C - C - H H H Butane: C 4 H 10

41 Structural Isomers of C 4 H 10

42 Isomers of Butane Timberlake, Chemistry 7 th Edition, page 383 H C CCC H H H H HHH H H C 4 H 10 butane propane or isobutane H C CCC H H H HH H H H H methyl

43 but-1-ene cis-but-2-ene trans-but-2-ene 2-methylpropene IUPAC name C4H8C4H8C4H8C4H8

44 Pentane C 5 H 12

45 Isomers of Pentane C 5 H 12 Timberlake, Chemistry 7 th Edition, page 385 These are called structural isomers.

46 H C CCC H H H H HHH H H Butane C 4 H 10 Butane C 4 H 8 H C CCC H H H HHH H 1-butene but(1)ene n-butene 2-butene 1 2 3 4 C CC H H HHH H C H H Butene C 4 H 8

47 H C CCC H H CH 3 H H H C C H H H H H hexane 3, 3 dimethyl 1 2 3 4 5 6 or 1 2 3 456 hexane 4, 4 dimethyl C CCC CH 3 C C Lowest sum of numbers is correct

48 C CCC C C C CH 3 CH 3 CHCH 2 CHCH 3 CH 3 H H H H H HH H HHH H H H H H C 7 H 16 H C CCC H H H H HHH H H C CC H H H HHH Heptane 2, 4-dimethyl pentane condensed structural formula shorthand molecular formula

49 H C CCC H H H H HHH H H C CC H H H HHH C H H H C H H C H C H H H C CC HH H C H H H C CC Br H H Cl

50 H CH H H C CC H H HHH C H H H 2 - methylbutane butane

51 C H H H C CC HH H C H H 1, 4 - pentadiene

52 HH C CC Cl H 3 - chloro 1 - propyne

53 H C CC Br H H Cl 3 - bromo, 1,1 -dichloro 1 - propene Recall: double bond is lowest number must put substituents in alphabetical order

54 Naming Branched Alkanes (IUPAC) 1.Root name: name of longest continuous C chain (parent chain) Two equally long? Choose the one with more branches 2.Number C atoms in chain, starting at end with first branch 3.Identify substituents, give each a number (C it is connected to) Two or more identical substituents: use prefixes (di-, tri-, tetra-, etc.) 4.List substituents alphabetically before root name Do not alphabetize prefixes 5.Punctuation: commas separate numbers from each other hyphens separate numbers from names no space between last substituent & root name 4-ethyl-3,5-dimethyloctane 1 2 3 6 5 8 7 4 4-ethyl 3-methyl and 5-methyl = 3,5-dimethyl Octane

55 Structural Isomers: Pentane (C 5 H 12 ) pentane 2-methylbutane 2,2-dimethylpropane

56 Structural Isomers: Hexane (C 6 H 14 ) hexane 2-methylpentane 3-methylpentane 2,3-dimethylbutane 2,2-dimethylbutane

57 Structural Isomers: Heptane (C 7 H 16 ) heptane 2-methylhexane 3-methylhexane 2,2-dimethylpentane 2,3-dimethylpentane

58 Structural Isomers: Heptane C 7 H 16 2,4-dimethylpentane 3,3-dimethylpentane 3-ethylpentane 2,2,3-trimethylbutane

59 Comparing Structural Isomers C 5 H 12 (Same formula, different structure) More branching → weaker London dispersion forces 36.0pentane 27.92-methylbutane 9.52,2-dimethylpropane Boiling point (°C) Name Structure BP/MP of Linear alkanes > BP/MP of branched alkanes

60 Naming Alkanes Problem Set 1. 2-methylbutane 2. 3. 4. 2-methylbutane 2,3-dimethylbutane3,3,4-trimethylhexane

61 Naming Alkanes Problem Set 5.3-ethyl-2,4,5-trimethylheptane 6.6-ethyl-2,7-dimethylnonane

62 Naming Alkanes Problem Set 7. 2,3,4-trimethylhexane 8. 9. 10. 4-ethyl-3-methylheptane 3,3,4-trimethylhexane 5-tert-butyl-4-isopropyl-3- methyloctane

63 Naming Alkanes Problem Set 11.2,2,3-trimethylheptane 12. 6-ethyl-2-methyl-5-propylnonane

64 Naming Alkanes Problem Set 13. 3,5-dimethyl-4-propylheptane 14. 15. 16. 3,4,4-trimethylheptane 3-ethyl-2,2,3- trimethylpentane 4-ethyl-6-isobutyl-2,9- dimethyldecane

65 Naming Alkanes Problem Set 17. 1,1,6-trimethylhexane 18. 2-tert-butyl-4-ethyl-3-isopropylpentane 1 2 3 4 5 6 7 8 6 1 2 3 4 5 7 2-methyloctane 4-isopropyl-2,2,3,5-tetramethylheptane

66 Naming Alkanes Problem Set 19. 1-sec-butyl-4-isobutyl-3-methylbutane 20. 4,5,5-trimethylhexane 1 2 3 4 5 6 7 2,5,8-trimethyldecane 2,2,3-trimethylhexane 1 2 3 4 5 6 7 8 9 10

67 H C CCC H H H HH H H C CC H H H HHH C H H H C H H C H H H 3,4-dimethyl octane

68 CH 3 CCH 2 Cl C H3CH3CC H 3, 4 - dichloro 4 - methyl 2 - hexene

69 Functional Groups Hydrocarbons in which some hydrogen atoms have been replaced can be compared to an electric drill with attachments. Inferring: What determines the function of the drill, the drill itself or the attachments? Forstner drill bit Philips screwdriver bit drum sander Twist drill bit hole saw bit Electric drill

70 Alcohols

71 Alcohols (R-OH) R = -CH 3 ‘methyl’ R = -CH 2 CH 3 ‘ethyl’ Methanol (methyl alcohol) Ethanol (ethyl alcohol) Timberlake, Chemistry 7 th Edition, page 437

72 Primary, Secondary, Tertiary Alcohols Primary (1 o ) Alcohol Secondary (2 o ) Alcohol Tertiary (3 o ) Alcohol (One alkyl group) (Two alkyl groups) (Three alkyl groups) Examples: R1R1 OH H H C R1R1 H R2R2 C R1R1 R3R3 R2R2 C CH 3 OH H H C CH 3 OH H CH 3 C OH CH 3 C Carbon attached to OH group Alkyl group 1o1o 2o2o 3o3o

73 Aldehydes and Ketones

74 Formaldehyde (CH 2 O) Acetaldehyde (CH 3 CH) Acetone (CH 3 COCH 3 ) Aldehyde R-C-H Ketone R-C-R' Timberlake, Chemistry 7 th Edition, page 453 dimethyl ketone, 2-propanone methanal ethanal, ethyl aldehyde O O O

75 Ethers

76 Dimethyl Ether Dimethyl ether – C 2 H 6 O – Flammable – anesthesia Timberlake, Chemistry 7 th Edition, page 446

77 Functional Groups

78 R- Functional Groups -CH 3 -CH 2 CH 3 -CH 2 CH 2 CH 2 CH 3 methyl ethyl propyl butyl -CH 2 CH 2 CH 3 CH 3 CHCH 2 CH 3 H sec-butyl – CH 2 – C – CH 3 H CH 3 isobutyl – C – CH 3 CH 3 tert-butyl CH 3 CCH 3 H isopropyl

79 Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 642

80 Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 660

81 Alkenes and Alkynes

82 Ball and stick model of Ethylene Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 651 Space filling model of Ethylene

83 Alkenes and Alkynes Alkene – Double bonds Alkynes – Triple bonds Timberlake, Chemistry 7 th Edition, page 409 A ball-and-stick model of ethene C 2 H 4, the simplest alkene. ethene A ball-and-stick model of acetylene (IUPAC name ethyne) ethyne (acetylene)

84 Saturated vs. Unsaturated Hydrocarbons Saturated – Single bonds Example: Unsaturated – Double & triple bonds Example:

85 Aliphatic Hydrocarbons Alkane AlkeneAlkyneAlkadiene General formula Typical structural formula Carbon-carbon bond type Naming suffix all single bondsone double bondone triple bondtwo double bonds -ane-ene-yne-diene C n H 2n + 2 C n H 2n C n H 2n - 2 1-butenebutane1-butyne1,3-butadiene – C = C – C – C – – C – C – C – C – – C = C – C = C – – C = C – C – C –

86 Hydrogenation vegetable oils + H 2 shortening stick margarine tub (soft) margarine unsaturated saturated (an addition reaction)

87 Cycloalkanes

88 Cycloalkanes Formula C n H 2n Cyclopropane Cyclobutane Cyclopentane Cyclohexane Condensed Structural Formula Geometric Formula Name

89 Cycloalkanes Formula C n H 2n Timberlake, Chemistry 7 th Edition, page 388 Cyclopropane Cyclobutane Cyclopentane Cyclohexane Condensed Structural Formula Geometric Formula Name

90 Benzene

91 Benzene An Aromatic Compound – C 6 H 6 – Resonance structures – Kekule’s dream

92

93 Benzene

94 Resonance in Benzene Kelter, Carr, Scott, Chemistry A World d of Choices 1999, page 212

95 Shorthand notation of Benzene

96 Structure of Benzene Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212 C C CC CC H H H H H H

97 Structure of Benzene Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212 C C CC CC H H H H H H

98 Structure of Benzene Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212 C C CC CC H H H H H H C C CC CC H H H H H H

99 Benzene 3-D – VSEPR Diagram Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212

100 Names of monosubstituted benzene rings Chlorobenzene Bromobenzene Nitrobenzene Toluene Phenol Styrene

101 Benzene NO 3 - Nitrobenzene Mark Wirtz, Edward Ehrat, David L. Cedeno*

102 Aromatic Hydrocarbons

103 Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 430

104 Cholesterol Compounds

105 C C CC CC CH 3 ortho position number name 1, 2 ortho- (o-) 1,3meta- (m-) 1,4para- (p-) 1 2 3 4 5 6 meta para

106 C C CC CC H CH 3 H H H ortho-dimethylbenzene or 1, 2 - dimethylbenzene 1 2 3 4 5 6

107 C C CC CC H CH 3 H H H meta-dimethylbenzene or 1, 3 - dimethylbenzene 1 2 3 4 5 6

108 C C CC CC H CH 3 H H H para-dimethylbenzene or 1, 4 - dimethylbenzene 1 2 3 4 5 6

109 C C CC CC H MD H H H para-docs or paradox 1 2 3 4 5 6

110 C C CC CC H MD H H H ortho-docs or orthodox 1 2 3 4 5 6

111 C C CC CC Fe 2+ ferrous wheel or ferris wheel 1 2 3 4 5 6

112 C C CC CC H NO 2 H H H o - dinitrobenzene or 1, 2 - dinitrobenzene

113 C C CC CC CH 3 NO 2 H O2NO2N H 2,4,6 - trinitrotoluene or TNT

114 C C CC CC Cl CH 3 Cl H H 2, 4, 6 -trichloromethylbenzene or 2, 4, 6 - trichlorotoluene Toluene

115 C C CC CC H O H H H COOH 2-acetyloxybenzoic acid or (acetylsalicylic acid or aspirin) CCH 3 O

116 C dichlorodiphenyltrichloroethane or DDT C C CC CC H H H H Cl C C C CC CC H H H H H CCl 3 Cl

117 C C CC CC H CH H H H H phenyl ethene or styrene CH 2 n poly aka (styrofoam)

118 Carboxylic Acids

119 Benzoic acid p-Nitrobenzoic acid CH 3 CHCH 2 CH 2 COOH Br 4-Bromopentanoic acid CH 2 CH 2 COOH Cl 3-Chloropropanoic acid R – C – OH = O R - COOH

120 Classes of Organic Compounds

121 Class of Compound halocarbon alcohol ether aldehyde ketone carboxylic acid ester amine amide Functional Group General Formula Example CH 3 Cl chloromethane CH 3 CH 2 CH 2 OH 1-propanol OH O C O C O C O C O O C O NH 2 F, Cl,Br, I OH O C O X C O C O C O O NH 2 C O R R RR’ R R R R R R CH 3 CH 2 CH 2 NH 2 propanamine CH 3 CCH 3 propanone O CH 3 CH 2 CH propanal O CH 3 CH 2 COH propanoic acid O CH 3 COCH 3 methylethanoate O CH 3 CH 2 CNH 2 propanamide O CH 3 OCH 2 CH 3 methoxyethane H

122 Organic Nomenclature Flow Chart

123 Functional Groups

124 Timberlake, Chemistry 7 th Edition, page 403

125 Order of Priority of Functional Groups 1 Carboxylic acid-COOH 2 Sulfonic acid-SO 3 H 3 Ester-COOR 4 Acid chloride-COCl 5 Amide-CONH 2 6 Nitrile-CN 7 Aldehyde-CHO 8 Ketone-CO 9 Alcohol-OH 10 Phenol-OH 11 Thiol-SH 12 Amine-NH 2 13 Ether-OR 14 Sulfide-SR Order of priority Functional groupFormula Order of priority Functional groupFormula Selinger, Chemistry in the Marketplace, 1994, page 23

126 Esters An ester is similar to a carboxylic acid, but the acidic hydrogen has been replaced by an alkyl group H O CCC H H OH H H a carboxylic acid H O CCC H CH 3 OH H H an ester methyl propanoate methyl group propanoic acid from propanoic acid R – C – O – R’ O

127 Naming Esters Name the following ester: CH 3 CH 2 CH 2 COCH 2 CH 3 O Step 1) the ester alkyl group (R’) = ethyl Step 2) the acid (R) = butanoic acid Step 3) the name = ethyl butanoate R – C – O – R’ O

128 Formation of an Ester H OH CCC H O HH H C H H+ H CH H H C H HO H O CCC H O HH H C H H + H CH H H C H H butyric acid (butanoic acid) ethyl alcohol ethyl butyrate (tastes and smells like pineapple)  water Ester Lab II Ester Lab II Ester Lab I Ester Lab I

129

130 H CCH H H H H C CC HH HOH 2-pentanone C 5 H 10 O Ketone R' RC O 12345

131 methyl propanoate C4H8O2C4H8O2 Ester H CH H C O CC H OH H H H O RC O R' 1 2 3 3 carbons = propane 1) Name the R' first 2) Find carbon chain and include the carbonyl carbon. 3) Drop the ending and add -yl (R' = methyl)

132 Ester H CCH 3 O HC O O RC O R' Raspberry CH 2 H O CC H OH C Banana CH 2 (CH 2 ) 6 H O CC H OH CH 3 Orange CH 3 PP PP Ester Lab PP PP Ester Lab

133 Ester O RC O R' CH 2 H O CC H OH CH 3 Pear Peach CH 2 H O CC H OH C C CC CC H H H H H

134 C C H C H H C OH O H C H H C H H H H 3-methylpentanoic acid C OH O R Carboxylic acid C 6 H 12 O 2 C OH O C O 1 2 345 H

135 H C CCC H H H H HHH H H O CC H H HH R' O R Ether ethyl butyl ether (common name) or ethoxybutane (IUPAC) C 6 H 14 O

136 H C CC H H H H H C CC H H HH OH C H H C H H H H H C 8 H 18 O 3-ethyl-3-hexanol OH R Alcohol

137 C OH O C H H H ethanoic acid C OH O R Carboxylic acid C2H4O2C2H4O2

138 H CCOH H H H C HO H H 1,3-propanediol OH R Alcohol C3H8O2C3H8O2

139 Draw structural formulas for the following: a. 3-heptene b. trichloromethane c. 2-chloro-3-phenylhexane d. 1,3-cyclopentadiene e. toluene (methylbenzene) f. 1,4-dibromobenzene g. 2-bromo-3-methyl-2-butene

140 Write the condensed formulas for the following haloalkanes: a. ethyl chloride (common name) or chloroethane (IUPAC) b. bromomethane c. 1-bromo-3-chlorocyclopentane d. 1,1-dichlorocyclohexane e. 2,2,3-trichlorobutane f. 2,4-dibromo-2,4-dichloropentane

141 Write a correct IUPAC (or common name) for the following: a. bromoethane (ethyl bromide) b. 2,3-dichlorobutane c. chlorocyclopentane d. 2-bromo-4-chlorohexane e. 1-chloro-1-fluorocyclobutane Cl F CH 3 CH 2 Br CH 3 CHCHCH 3 Cl CH 3 CH 2 CHCH 2 CHCH 3 Cl Br

142 Draw structures for the following: 1,1,1-trifluoroethane cis-2-butene 1-heptyne 2-chloro-4,5-diethylnonane cyclohexane ethylcyclopropane meta-dichlorobenzene 2,4,6-trinitrotoluene ortho-iodotoluene ethyl pentanoate 2-bromohexanal methyl propanamide propoxypropane (propylpentyl ether) m-iodophenol 1,3-propanedioic acid propylamine 1,4-butandiol 3-chloropentanoic acid 1,3-dibromo-2-propanone methyl-3-chloropropyl ether 3-hydroxy-1-pentyne

143 F CCH H H F F 1,1,1-trifluoroethane C2H3F3C2H3F3

144 cis-2-butene CH 3 CC H H H3CH3C C4H8C4H8 trans-2-butene CH 3 CC H H H3CH3C

145 H C CCC H H H H HHH H C CC H H HH H 1-heptyne C 7 H 12

146 H C CCC H H H H HHH H H C CC H H H HHH C H H H C H H C H C H H H C CC HH H C H H H C CC Br H H Cl

147 Chirality

148 Chirality: Chiral vs. Achiral Chiral Achiral right shoe left mitt right-handed glass plate scissors tennis racket

149 H Br I Cl Chirality Timberlake, Chemistry 7 th Edition, page 484 H Cl I Br H I Cl mirror H Cl I Br

150 “cis” and “trans” isomers cis-2-butene trans-2-butene Timberlake, Chemistry 7 th Edition, page 414 C = C CH 3 H3CH3C H H C = C CH 3 H3CH3C H H Geometric Isomers (same side) (opposite side)

151 Isomerism Geometric Isomers trans cis Stereoisomers (Structural Isomers) mirror images

152 Other Functional Groups to Recognize EthersAminesAmides (“EETH erz”)(“uh MEENZ”)(“uh MIDZ” or “AM idz”) –O– –N –C–N = O “coca-ine” “caffe-ine” “Tatoo-ine”

153 Organic Reactions combustion of hydrocarbons OR compounds w /only C, H, and O: products are… CO 2 and H 2 O Write the equation for the complete combustion of 2-methyl-2-pentene. Write the equation for the complete combustion of ethylbutanoate.  C 6 H 12 + O 2 CO 2 + H 2 O 669 O O  C 6 H 12 O 2 + O 2 CO 2 + H 2 O 668

154 substitution: an H atom is removed and “something else” is put in its place -- In halogenation, a _______ atom replaces an H. halogen Write an equation for the reaction between ethane and chlorine. + Cl 2  –C–C–H HH H HH –C–C–Cl HH H HH + HCl If more chlorine is provided, the reaction will produce... AND SO ON. –C–C–Cl HH H HH + Cl 2  –C–C–Cl HH Cl HH + HCl

155 Substitution occurs with aromatic compounds, too. + Br 2 catalyst + CH 3 CH 2 Cl catalyst Br + HBr+ HCl Ethylbenzene is an important intermediate in the production of styrene which, in turn, is used to make polystyrene. Roughly 25 million tons of ethylbenzene are produced and used every year.

156 addition: a multiple bond is broken and two “things” are inserted + Br 2 H C=C H HH –C–C–Br HH Br HH + HBr H C=C H HH –C–C–Br HH H HH + H 2 O H C=C H HH –C–C–OH HH H HH H 2 SO 4 H–C–C–C–C–H H H H H + Cl 2 –C–C=C–C– ClHH HH HH

157 A specific addition rxn is hydrogenation, in which __ is added across a multiple C-C bond. H -- requires a catalyst (usually a finely-divided _____) to rupture the multiple bond metal –C–C–H HH H HH + H 2 H C=C H HH catalyst Another addition reaction is polymerization. “lots” of ethylene H C=C H HH H H HH H H HH polyethylene –C–C–C–C– HH HH HH HH

158 condensation (or elimination, or dehydration): _____ is a product water -- One reactant provides an __, the other provides an ___. H OH CH 3 CH 2 OH + CH 3 OH NO 2 + H 2 O + HNO 3 H 2 SO 4 CH 3 CH 2 –O–CH 3 + H 2 O wateralcohol m’c an ether Complex protein molecules are made from condensation reactions of amino acids.

159 -- Amides can be formed in condensation rxns between carboxylic acids and amines. Write the equation for the reaction between butanoic acid and nitrogen trihydride. O OH + NH 3 O NH 2 + H 2 O carboxylic acidamineamidewater Ammonia is the simplest amine.

160 Esterification is a condensation reaction between a carboxylic acid and an alcohol. Write the equation for the reaction between butanoic acid and 1-butanol. O OH HO + O O + H 2 O butanoate butyl (the active substance in the characteristic flavor/odor of pineapple)

161 Write the equation for the reaction between 3-phenyl-2-propenoic acid and ethanol. O OH HO + H2OH2O + -3-phenyl-2-propenoate (the active substance in the characteristic flavor/odor of cinnamon) ethyl (i.e, ethyl cinnamate ) “When in doubt, make water.” Mr. B O O

162 Amino Acid

163 AmineAmmoniaAmmonium ion NH 2 1- NH 3 NH 4 1+

164 Polymers

165 World of Chemistry The Annenberg Film Series VIDEO ON DEMAND How chemists control the molecular structure to create polymers with special properties is explored. Episode 22 Episode 22 – Polymers

166 Polymers polymer monomer homo Jaffe, New World of Chemistry, 1955, page 603 chain

167 copolymer monomer

168 Copyright © 2007 Pearson Benjamin Cummings. All rights reserved.

169 Polymerization Polymers = Monomer + Monomer + … Synthetic Polymers – Nylon – “plastics” – Vulcanized rubber – polyethylene Natural Polymers – Silk – Proteins (amino acids) – Starch (sugars)

170 Polymers Ethene (ethylene) Chloroethene (vinyl chloride) Polyethylene Polyvinyl chloride (PVC) Plastic bottles, film, insulation material Plastic pipes and tubing, garden hoses, garbage bags H 2 C = CH 2 – CH 2 – CH 2 – CH 2 – CH 2 – H 2 C = CH Cl – CH2 – CH – CH 2 – CH – Cl

171 Polymers Teflon Tetrafluoroethene Ski and hiking clothing, carpets, artificial joints Nonstick coatings Propene (propylene) CH 3 CH = CH 2 – CH 2 – CH – CH 2 – CH – Polypropylene CH 3 F – C = C – F FF – C – C – C – C – FFFF FFFF

172 Polymers Polystyrene Plastic film and wrap Plastic coffee cups and cartons, insulation Phenylethene H 2 C = CH– CH 2 – CH – CH 2 – CH – 1,1 Dichloroethene H 2 C = C – Cl Cl – CH 2 – C – CH 2 – C – Saran Cl

173 Slime PVA + PVA + PVA – With cross-linking agent (borax solution)

174 What are some things you think of when I say organic? Medicine Plastics Soil Soap Petroleum Grass Clothing PRISM fellow: Mr. Kevin J. Hodel

175 Organic - the study of carbon containing compounds that their properties Why carbon?? Strong bonds between carbons Low reactivity of carbon compounds Geometry of carbon compounds PRISM fellow: Mr. Kevin J. Hodel

176 Diamonds PRISM fellow: Mr. Kevin J. Hodel

177 Graphite PRISM fellow: Mr. Kevin J. Hodel

178 Polymers Polymer - a large organic molecule composed of smaller units bonded together –These smaller units are called monomers. Tires –Vulcanized rubber was discovered by mistake!! soft and weak until heated then forms disulfide linkages between the rubber polymers. PRISM fellow: Mr. Kevin J. Hodel

179 Natural Polymers Rubber Cotton Paper –Cotton and paper are made of cellulose which is the most abundant natural polymer in the world. Starch –Potatoes, corn, bread PRISM fellow: Mr. Kevin J. Hodel

180 Synthetic Polymers Half of the industrial chemists work in some area of polymer chemistry. In 1996, more than 270 lbs of plastic was produced per person in the US. PRISM fellow: Mr. Kevin J. Hodel

181

182 Types of Synthetic Polymers Elastomers - can be highly stretched and returns to their original shape. Fibers - polymers that exhibit little or no elasticity (threadlike) Plastics - synthetic polymers that are more elastic than fibers but less elastic the elastomers. PRISM fellow: Mr. Kevin J. Hodel

183 Common Polymers Polystyrene foam can be made into cartons to protect eggs or into packing “peanuts” to cushion fragile objects for shipping. Polyethylene: You probably see polyethylene every day! It’s the plastic used to make many containers, among other things. Water-resistant paints and varnishes derive from a family of synthetic polymers called acrylics. PRISM fellow: Mr. Kevin J. Hodel Polystyrene Plastic coffee cups and cartons, insulation – CH 2 – CH – CH 2 – CH – Polyethylene Plastic bottles, film, insulation material – CH 2 – CH 2 – CH 2 – CH 2 –

184 Recycling Before: Milk jug. After: Picnic table. Before: Bread bag. After: Trash can. Before: Sandwich box. After: Frisbee. PRISM fellow: Mr. Kevin J. Hodel

185 Plastic Resin Codes

186 Copyright © 2007 Pearson Benjamin Cummings. All rights reserved.

187 Addition Reactions H CC H H H H H Br CC H H H H H CC H HH H CC H HH Ni H – H + Ni Br – Br +

188 Acid-Catalyzed Hydration H CC OH H H H H H CC H HH H 2 SO 4 H – OH + ethene ethanolwater Write out the mechanism for the formation of isopropyl alcohol (used as rubbing alcohol), from propene. OH CC H H H H H H CC H HH H – OH H 2 SO 4 + ethene ethanolwater

189 Molecular Geometry H H H H 109.5 o C Linear Trigonal planar Tetrahedral Trigonal pyramidal Bent 109.5 o 107.3 o 104.5 o H 2 O CH 4 AsCl 3 AsF 5 BeH 2 BF 3 CO 2 180 o

190 Order of Priority of Functional Groups 1 Carboxylic acid-COOH 2 Sulfonic acid-SO 3 H 3 Ester-COOR 4 Acid chloride-COCl 5 Amide-CONH 2 6 Nitrile-CN 7 Aldehyde-CHO 8 Ketone-CO 9 Alcohol-OH 10 Phenol-OH 11 Thiol-SH 12 Amine-NH 2 13 Ether-OR 14 Sulfide-SR Order of priority Functional groupFormula Order of priority Functional groupFormula Selinger, Chemistry in the Marketplace, 1994, page 23

191 Resources - Organic Objectives Functional Groups Quiz Functional Groups Quiz Episode 21 Episode 21 - Carbon Episode 22 Episode 22 - Polymers


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