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Organic Chemistry The Chemistry of Carbon Slide 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 Slide 3 World of Chemistry The Annenberg Film Series VIDEO ON DEMAND Organic chemistry is the study of carbon compounds. The versatility of carbons molecular structures provides the enormous range of properties of its compounds. Episode 21 Episode 21 Carbon Slide 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 Slide 5 Friedrich Whler Made the first organic compound from non-living substances. Shot down the Vital Force idea of organic substances. Slide 6 Distilling Crude Oil Slide 7 Fractional Distillation of Crude Oil Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 429 Slide 8 Slide 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 Slide 10 Distilling Crude Oil Separate fractions based on differences in boiling point. Slide 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 Slide 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) Slide 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 Slide 14 Methane Slide 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 Slide 16 Methane is Tetrahedral H H H H C Slide 17 Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 634 Slide 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 Slide 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 Slide 20 Ethane Slide 21 H CCH H H H H Lewis structure of Ethane Slide 22 Space filling model of Ethane Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635 Slide 23 Ball and Stick model of Ethane Slide 24 Propane Slide 25 Structure of Propane Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635 Slide 26 Butane Slide 27 Structure of Butane Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635 Slide 28 Ball and Stick Models Ethane C 2 H 6 Propane C 3 H 8 Timberlake, Chemistry 7 th Edition, page 366 Slide 29 Hydrocarbons Slide 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 Slide 31 Hydrocarbons (alkanes) Slide 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 Slide 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 Slide 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 Slide 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 Slide 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.) Slide 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 Slide 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 Slide 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 Dont allow children to name alkanes unattended Slide 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 Slide 41 Structural Isomers of C 4 H 10 Slide 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 Slide 43 but-1-ene cis-but-2-ene trans-but-2-ene 2-methylpropene IUPAC name C4H8C4H8C4H8C4H8 Slide 44 Pentane C 5 H 12 Slide 45 Isomers of Pentane C 5 H 12 Timberlake, Chemistry 7 th Edition, page 385 These are called structural isomers. Slide 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 Slide 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 Slide 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 Slide 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 Slide 50 H CH H H C CC H H HHH C H H H 2 - methylbutane butane Slide 51 C H H H C CC HH H C H H 1, 4 - pentadiene Slide 52 HH C CC Cl H 3 - chloro 1 - propyne Slide 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 Slide 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 Slide 55 Structural Isomers: Pentane (C 5 H 12 ) pentane 2-methylbutane 2,2-dimethylpropane Slide 56 Structural Isomers: Hexane (C 6 H 14 ) hexane 2-methylpentane 3-methylpentane 2,3-dimethylbutane 2,2-dimethylbutane Slide 57 Structural Isomers: Heptane (C 7 H 16 ) heptane 2-methylhexane 3-methylhexane 2,2-dimethylpentane 2,3-dimethylpentane Slide 58 Structural Isomers: Heptane C 7 H 16 2,4-dimethylpentane 3,3-dimethylpentane 3-ethylpentane 2,2,3-trimethylbutane Slide 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 Slide 60 Naming Alkanes Problem Set 1. 2-methylbutane 2. 3. 4. 2-methylbutane 2,3-dimethylbutane3,3,4-trimethylhexane Slide 61 Naming Alkanes Problem Set 5.3-ethyl-2,4,5-trimethylheptane 6.6-ethyl-2,7-dimethylnonane Slide 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 Slide 63 Naming Alkanes Problem Set 11.2,2,3-trimethylheptane 12. 6-ethyl-2-methyl-5-propylnonane Slide 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 Slide 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 Slide 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 Slide 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 Slide 68 CH 3 CCH 2 Cl C H3CH3CC H 3, 4 - dichloro 4 - methyl 2 - hexene Slide 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 Slide 70 Alcohols Slide 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 Slide 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 Slide 73 Aldehydes and Ketones Slide 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 Slide 75 Ethers Slide 76 Dimethyl Ether Dimethyl ether C 2 H 6 O Flammable anesthesia Timberlake, Chemistry 7 th Edition, page 446 Slide 77 Functional Groups Slide 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 Slide 79 Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 642 Slide 80 Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 660 Slide 81 Alkenes and Alkynes Slide 82 Ball and stick model of Ethylene Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 651 Space filling model of Ethylene Slide 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) Slide 84 Saturated vs. Unsaturated Hydrocarbons Saturated Single bonds Example: Unsaturated Double & triple bonds Example: Slide 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 Slide 86 Hydrogenation vegetable oils + H 2 shortening stick margarine tub (soft) margarine unsaturated saturated (an addition reaction) Slide 87 Cycloalkanes Slide 88 Cycloalkanes Formula C n H 2n Cyclopropane Cyclobutane Cyclopentane Cyclohexane Condensed Structural Formula Geometric Formula Name Slide 89 Cycloalkanes Formula C n H 2n Timberlake, Chemistry 7 th Edition, page 388 Cyclopropane Cyclobutane Cyclopentane Cyclohexane Condensed Structural Formula Geometric Formula Name Slide 90 Benzene Slide 91 Benzene An Aromatic Compound C 6 H 6 Resonance structures Kekules dream Slide 92 Slide 93 Benzene Slide 94 Resonance in Benzene Kelter, Carr, Scott, Chemistry A World d of Choices 1999, page 212 Slide 95 Shorthand notation of Benzene Slide 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 Slide 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 Slide 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 Slide 99 Benzene 3-D VSEPR Diagram Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212 Slide 100 Names of monosubstituted benzene rings Chlorobenzene Bromobenzene Nitrobenzene Toluene Phenol Styrene Slide 101 Benzene NO 3 - Nitrobenzene Mark Wirtz, Edward Ehrat, David L. Cedeno* Slide 102 Aromatic Hydrocarbons Slide 103 Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 430 Slide 104 Cholesterol Compounds Slide 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 Slide 106 C C CC CC H CH 3 H H H ortho-dimethylbenzene or 1, 2 - dimethylbenzene 1 2 3 4 5 6 Slide 107 C C CC CC H CH 3 H H H meta-dimethylbenzene or 1, 3 - dimethylbenzene 1 2 3 4 5 6 Slide 108 C C CC CC H CH 3 H H H para-dimethylbenzene or 1, 4 - dimethylbenzene 1 2 3 4 5 6 Slide 109 C C CC CC H MD H H H para-docs or paradox 1 2 3 4 5 6 Slide 110 C C CC CC H MD H H H ortho-docs or orthodox 1 2 3 4 5 6 Slide 111 C C CC CC Fe 2+ ferrous wheel or ferris wheel 1 2 3 4 5 6 Slide 112 C C CC CC H NO 2 H H H o - dinitrobenzene or 1, 2 - dinitrobenzene Slide 113 C C CC CC CH 3 NO 2 H O2NO2N H 2,4,6 - trinitrotoluene or TNT Slide 114 C C CC CC Cl CH 3 Cl H H 2, 4, 6 -trichloromethylbenzene or 2, 4, 6 - trichlorotoluene Toluene Slide 115 C C CC CC H O H H H COOH 2-acetyloxybenzoic acid or (acetylsalicylic acid or aspirin) CCH 3 O Slide 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 Slide 117 C C CC CC H CH H H H H phenyl ethene or styrene CH 2 n poly aka (styrofoam) Slide 118 Carboxylic Acids Slide 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 Slide 120 Classes of Organic Compounds Slide 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 Slide 122 Organic Nomenclature Flow Chart Slide 123 Functional Groups Slide 124 Timberlake, Chemistry 7 th Edition, page 403 Slide 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 Slide 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 Slide 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 Slide 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 Slide 129 Slide 130 H CCH H H H H C CC HH HOH 2-pentanone C 5 H 10 O Ketone R' RC O 12345 Slide 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) Slide 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 Slide 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 Slide 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 Slide 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 Slide 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 Slide 137 C OH O C H H H ethanoic acid C OH O R Carboxylic acid C2H4O2C2H4O2 Slide 138 H CCOH H H H C HO H H 1,3-propanediol OH R Alcohol C3H8O2C3H8O2 Slide 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 Slide 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 Slide 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 Slide 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 Slide 143 F CCH H H F F 1,1,1-trifluoroethane C2H3F3C2H3F3 Slide 144 cis-2-butene CH 3 CC H H H3CH3C C4H8C4H8 trans-2-butene CH 3 CC H H H3CH3C Slide 145 H C CCC H H H H HHH H C CC H H HH H 1-heptyne C 7 H 12 Slide 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 Slide 147 Chirality Slide 148 Chirality: Chiral vs. Achiral Chiral Achiral right shoe left mitt right-handed glass plate scissors tennis racket Slide 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 Slide 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) Slide 151 Isomerism Geometric Isomers trans cis Stereoisomers (Structural Isomers) mirror images Slide 152 Other Functional Groups to Recognize EthersAminesAmides (EETH erz)(uh MEENZ)(uh MIDZ or AM idz) O N CN = O coca-ine caffe-ine Tatoo-ine Slide 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 Slide 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 CCH HH H HH CCCl HH H HH + HCl If more chlorine is provided, the reaction will produce... AND SO ON. CCCl HH H HH + Cl 2 CCCl HH Cl HH + HCl Slide 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. Slide 156 addition: a multiple bond is broken and two things are inserted + Br 2 H C=C H HH CCBr HH Br HH + HBr H C=C H HH CCBr HH H HH + H 2 O H C=C H HH CCOH HH H HH H 2 SO 4 HCCCCH H H H H + Cl 2 CC=CC ClHH HH HH Slide 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 CCH 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 CCCC HH HH HH HH Slide 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 OCH 3 + H 2 O wateralcohol mc an ether Complex protein molecules are made from condensation reactions of amino acids. Slide 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. Slide 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) Slide 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 Slide 162 Amino Acid Slide 163 AmineAmmoniaAmmonium ion NH 2 1- NH 3 NH 4 1+ Slide 164 Polymers Slide 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 Slide 166 Polymers polymer monomer homo Jaffe, New World of Chemistry, 1955, page 603 chain Slide 167 copolymer monomer Slide 168 Copyright 2007 Pearson Benjamin Cummings. All rights reserved. Slide 169 Polymerization Polymers = Monomer + Monomer + Synthetic Polymers Nylon plastics Vulcanized rubber polyethylene Natural Polymers Silk Proteins (amino acids) Starch (sugars) Slide 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 Slide 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 Slide 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 Slide 173 Slime PVA + PVA + PVA With cross-linking agent (borax solution) Slide 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 Slide 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 Slide 176 Diamonds PRISM fellow: Mr. Kevin J. Hodel Slide 177 Graphite PRISM fellow: Mr. Kevin J. Hodel Slide 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 Slide 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 Slide 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 Slide 181 Slide 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 Slide 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! Its 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 Slide 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 Slide 185 Plastic Resin Codes Slide 186 Copyright 2007 Pearson Benjamin Cummings. All rights reserved. Slide 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 + Slide 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 Slide 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 Slide 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 Slide 191 Resources - Organic Objectives Functional Groups Quiz Functional Groups Quiz Episode 21 Episode 21 - Carbon Episode 22 Episode 22 - Polymers