Organic Chemistry The Chemistry of Carbon 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 Organic Chemistry Organic Chemistry: The chemistry of carbon and carbon-based compounds 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 Friedrich Wöhler Made the first organic compound from non-living substances. Shot down the Vital Force idea of organic substances. Distilling Crude Oil Fractional Distillation of Crude Oil Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 429 Energy Sources in United States 100 91 Percent 80 71 70 60 58 50 40 40 21 20 26 20 9 5 10 3 16 10 0 1850 Wood 1900 Coal Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 648 1940 1980 Petroleum / natural gas 1990 Hydro and nuclear Distilling Crude Oil Separate fractions based on differences in boiling point. American Petroleum Usage AMERICAN PETROLEUM USAGE A Lesson in Economics 1 Barrel of Petroleum 93% Energy Marketplace 7% Materials Marketplace (42 gallons) 42 Gallons of Crude Petroleum 36 Gallons Fuel At $3.00 per gallon 36 Gallons Fuel 19 Gallons Gasoline (11 Gallons in 1920) $108.00 OR 7% (3 Gallons Crude) At $20.00 per shirt 100 Nylon Shirts $2000.00 Entrepreneurs: [Put an alligator on the shirt and make even more $$$$$] London Dispersion Forces The temporary separations of charge that lead to the London force attractions are what attract one nonpolar molecule to its neighbors. Boiling points of simple hydrocarbons in degrees Kelvin 400 C8H18 350 Temperature (Kelvin) London forces increase with the size of the molecules. Fritz London 1900-1954 300 C5H12 C4H10 250 C3H8 200 C2H6 150 100 CH4 50 50 100 Molecular Weight 150 London Forces in Hydrocarbons 400 Boiling points of simple hydrocarbons in degrees Kelvin C8H18 350 C5H12 300 C4H10 250 C3H8 200 150 100 Simple hydrocarbons have only London dispersion forces as intermolecular forces C2H6 CH4 50 50 100 Molecular Weight 150 H H CH4 H C H H molecular formula structural formula H C 109.5o H H molecular shape H C H H H tetrahedral shape of methane tetrahedron ball-and-stick model Methane is Tetrahedral Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 634 Methane molecular formula structural formula molecular shape H CH4 H C H H H H ball-and-stick model C H 109.5o H Methane H C H H H tetrahedron tetrahedral shape of methane ball-and-stick model of methane Timberlake, Chemistry 7th Edition, page 365 Lewis structure of Ethane H Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635 H H C C H H H Space filling model of Ethane Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635 Ball and Stick model of Ethane Structure of Propane Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635 Structure of Butane Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635 Ball and Stick Models Ethane Timberlake, Chemistry 7th Edition, page 366 C2H6 Propane C3H8 First Ten Hydrocarbons Number of Carbon Atoms Molecular Formula Methane 1 CH4 CH4 Ethane 2 C2H6 CH3CH3 Propane 3 C3H8 CH3CH2CH3 Butane 4 C4H10 CH3CH2CH2CH3 Pentane 5 C5H12 CH3CH2CH2CH2CH3 Hexane 6 C6H14 CH3CH2CH2CH2CH2CH3 Heptane 7 C7H16 CH3CH2CH2CH2CH2CH2CH3 Octane 8 C8H18 CH3CH2CH2CH2CH2CH2CH2CH3 Nonane 9 C9H20 CH3CH2CH2CH2CH2CH2CH2CH2CH3 Decane 10 C10H22 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 Name Condensed Structural Formula Hydrocarbons (alkanes) First Ten Hydrocarbons Number of Carbon Atoms Molecular Formula Melting Point, oC Boiling Point, oC # of Isomers Methane 1 CH4 -182.5 -161.5 0 Ethane 2 C2H6 -183.2 -88.6 0 n-Propane 3 C3H8 -187.7 -42.1 0 n-Butane 4 C4H10 -138.3 -0.5 2 n-Pentane 5 C5H12 -129.7 36.1 3 n-Hexane 6 C6H14 -95.3 68.7 5 n-Heptane 7 C7H16 -90.6 98.4 9 n-Octane 8 C8H18 -56.8 125.7 18 n-Nonane 9 C9H20 -53.6 150.8 35 n-Decane 10 C10H22 -29.7 174.0 75 Name Increasing mass and boiling point Methane 16 g/mol -161.5oC Ethane 30 g/mol -88.6oC Copyright © 2007 Pearson Benjamin Cummings. All rights reserved. Propane 44 g/mol -42.1oC n-Butane 58 g/mol -0.5oC Hydrocarbons Number of Carbon Atoms Alkanes CnH2n + 2 Alkenes CnH2n Alkynes CnH2n-2 1 CH4 Methane ____ _______ ____ _______ 2 C2H6 Ethane C2H4 Ethene C2H2 Ethyne 3 C3H8 Propane C3H6 Propene C3H4 Propyne 4 C4H10 Butane C4H8 Butene C4H6 Butyne 5 C5H12 Pentane C5H10 Pentene C5H8 Pentyne 6 C6H14 Hexane C6H12 Hexene C6H10 Hexyne 7 C7H16 Heptane C7H14 Heptene C7H12 Heptyne 8 C8H18 Octane C8H16 Octene C8H14 Octyne 9 C9H20 Nonane C9H18 Nonene C9H16 Nonyne 10 C10H22 Decane C10H20 Decene C10H18 Decyne 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.) H H C H H H H H H H H H H H Methane CH4 Butane C4H10 H ? R C H H Methyl -CH3 C C C C H H H H H R C C C C H H H H H Butyl -C4H9 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 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 Butane Butane: C4H10 H H H H H-C-C-C-C-H H H H H Butane Gas – lighters Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 107 Structural Isomers of C4H10 butane H H H H H C C C C H H H H H Isomers of Butane C4H10 H HH H C H H methyl propane or isobutane Timberlake, Chemistry 7th Edition, page 383 C C C H H H H Isomers of Pentane C5H12 These are called structural isomers. Timberlake, Chemistry 7th Edition, page 385 H H H H H H C C C C H Butane C4H10 C C C C H H 3 3 4 4 H H Butene Butane C4H8 H 2-butene 2 n-butene H H H 2 1 1-butene H 1 C C C C H H H H H H H H H H but(1)ene H H CH3 H C C C 1 6 52 43 CH3 CH3 H H C H 3 4 C C C C C C H C H 25 CH3 H C H 16 H 3, 3 dimethyl hexane or Lowest sum of numbers is correct 4, 4 dimethyl hexane H H H H C CH3H H H CH CHCH CHCH C 3C C 2C C 3H H H H H CH 3 H C H C7H16 2, 4-dimethyl pentane H H molecular formula H H H condensed structural formula H H H H H C C C C C C C H H H H H H H H Heptane shorthand H H H H H H H H C H H C C C C C C C H H H H H H H H H H H H C C Cl H H C C C Br H Cl H H H C C H H C H H C C H H H H H H C C C C H H H H H C H H butane 2 - methylbutane H H H C C H H C H C C H 1, 4 - pentadiene H H H C C C H Cl 3 - chloro 1 - propyne H H Cl H C C C Br Cl 3 - bromo, 1,1 -dichloro 1 - propene Recall: double bond is lowest number must put substituents in alphabetical order Naming Branched Alkanes (IUPAC) Octane 4-ethyl 6 8 7 2 5 4 3 4-ethyl-3,5-dimethyloctane 1 3-methyl and 5-methyl = 3,5-dimethyl 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 Structural Isomers: Pentane (C5H12) pentane 2-methylbutane 2,2-dimethylpropane Structural Isomers: Hexane (C6H14) hexane 2,3-dimethylbutane 2-methylpentane 2,2-dimethylbutane 3-methylpentane Structural Isomers: Heptane (C7H16) heptane 2,2-dimethylpentane 2-methylhexane 2,3-dimethylpentane 3-methylhexane Structural Isomers: Heptane C7H16 2,4-dimethylpentane 3-ethylpentane 3,3-dimethylpentane 2,2,3-trimethylbutane Comparing Structural Isomers C5H12 Structure (Same formula, different structure) Name Boiling point (°C) pentane 36.0 2-methylbutane 27.9 2,2-dimethylpropane 9.5 More branching → weaker London dispersion forces BP/MP of Linear alkanes > BP/MP of branched alkanes Naming Alkanes Problem Set 1. 2. 2-methylbutane 2-methylbutane 4. 3. 2,3-dimethylbutane 3,3,4-trimethylhexane Naming Alkanes Problem Set 5. 3-ethyl-2,4,5-trimethylheptane 6. 6-ethyl-2,7-dimethylnonane Naming Alkanes Problem Set 7. 8. 2,3,4-trimethylhexane 9. 3,3,4-trimethylhexane 4-ethyl-3-methylheptane 10. 5-tert-butyl-4-isopropyl-3methyloctane Naming Alkanes Problem Set 11. 2,2,3-trimethylheptane 12. 6-ethyl-2-methyl-5-propylnonane Naming Alkanes Problem Set 13. 14. 3,5-dimethyl-4-propylheptane 15. 3-ethyl-2,2,3trimethylpentane 3,4,4-trimethylheptane 16. 4-ethyl-6-isobutyl-2,9dimethyldecane Naming Alkanes Problem Set 17. 1,1,6-trimethylhexane 4 6 8 2 1 18. 3 5 2-methyloctane 7 2-tert-butyl-4-ethyl-3-isopropylpentane 1 6 2 3 4 7 5 4-isopropyl-2,2,3,5-tetramethylheptane Naming Alkanes Problem Set 1-sec-butyl-4-isobutyl-3-methylbutane 19. 4 6 5 2 1 10 8 3 9 7 2,5,8-trimethyldecane 20. 4,5,5-trimethylhexane 4 2 1 6 3 5 7 2,2,3-trimethylhexane H H C H 3-ethyl 4-methyl heptane H C H H H H H H H C C C C C H H H H H C H H H C C H H H Cl Cl H3C C C C CH2 CH3 H CH3 3, 4 - dichloro 4 - methyl 2 - hexene 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? Electric drill Forstner drill bit hole saw bit Twist drill bit Philips screwdriver bit drum sander Alcohols (R-OH) Methanol (methyl alcohol) Ethanol R = -CH3 ‘methyl’ R = -CH2CH3 ‘ethyl’ Timberlake, Chemistry 7th Edition, page 437 (ethyl alcohol) Primary, Secondary, Tertiary Alcohols Primary (1o) Alcohol Carbon attached to OH group H R1 Alkyl group C Secondary (2o) Alcohol OH R1 H Tertiary (3o) Alcohol R2 C R2 OH R1 C H R3 CH3 CH3 OH Examples: H CH3 C OH CH3 C OH CH3 C H H CH3 1o 2o 3o (One alkyl group) (Two alkyl groups) OH (Three alkyl groups) Aldehydes and Ketones O Aldehyde O Ketone Acetaldehyde ethanal, ethyl aldehyde O (CH3CH) Timberlake, Chemistry 7th Edition, page 453 Formaldehyde methanal (CH2O) R-C-H R-C-R' Acetone dimethyl ketone, 2-propanone (CH3COCH3) Dimethyl Ether Dimethyl ether – C2H6O – Flammable – anesthesia Timberlake, Chemistry 7th Edition, page 446 R- Functional Groups -CH3 methyl -CH2CH3 ethyl -CH2CH2CH2CH3 H CH3CHCH2CH3 -CH2CH2CH3 propyl sec-butyl H – CH2 – C – CH3 isobutyl CH3 H CH3CCH3 butyl isopropyl CH3 – C – CH3 CH3 tert-butyl Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 642 Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 660 Ball and stick model of Ethylene Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 651 Alkenes and Alkynes Alkene – Double bonds ethene Alkynes A ball-and-stick model of ethene C2H4, the simplest alkene. – Triple bonds ethyne (acetylene) A ball-and-stick model of acetylene (IUPAC name ethyne) Timberlake, Chemistry 7th Edition, page 409 Saturated vs. Unsaturated Hydrocarbons Saturated – Single bonds Example: Unsaturated – Double & triple bonds Example: Aliphatic Hydrocarbons Alkane Alkene Alkyne Alkadiene General formula CnH2n + 2 CnH2n CnH2n - 2 Typical structural formula –C–C–C–C– –C=C–C–C– –C =C–C–C– –C=C–C=C– butane 1-butene 1-butyne 1,3-butadiene all single bonds one double bond one triple bond two double bonds -ane -ene -yne -diene Carbon-carbon bond type Naming suffix CnH2n - 2 Hydrogenation (an addition reaction) tub (soft) margarine + H2 vegetable oils unsaturated shortening saturated stick margarine Cycloalkanes Formula CnH2n Condensed Structural Formula H2 C H2C CH2 Geometric Formula Name Cyclopropane H2 H2C C C CH2 H2 H2C H2 C CH2 C C H2 H2 H2C H2C Cyclobutane H2 C C H2 Cyclopentane CH2 CH2 Cyclohexane Cycloalkanes Formula CnH2n Condensed Structural Formula Geometric Formula Name Cyclopropane Cyclobutane Cyclopentane Cyclohexane Timberlake, Chemistry 7th Edition, page 388 Benzene An Aromatic Compound – C6H6 – Resonance structures – Kekule’s dream Benzene Resonance in Benzene Kelter, Carr, Scott, Chemistry A World d of Choices 1999, page 212 Shorthand notation of Benzene Structure of Benzene H H C C C H H C C H Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212 C H Structure of Benzene H H C C C H H C C H Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212 C H Structure of Benzene H H C C C H H C C H Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212 C H Benzene 3-D – VSEPR Diagram Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212 Cl Names of monosubstituted benzene rings Chlorobenzene CH3 Toluene Br OH Bromobenzene Phenol NO2 Nitrobenzene CH=CH2 Styrene Benzene Mark Wirtz, Edward Ehrat, David L. Cedeno* NO3- Nitrobenzene Aromatic Hydrocarbons Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 430 Cholesterol Compounds CH3 6 C C 1 C ortho C 2 5 C para 4 C 3 meta position number 1, 2 1,3 1,4 name ortho- (o-) meta- (m-) para- (p-) CH3 H 6 C C 1 C CH3 H C 2 5 C H 4 C 3 H ortho-dimethylbenzene or 1, 2 - dimethylbenzene CH3 H 6 C C 1 C H H C 2 5 C H 4 C 3 CH3 meta-dimethylbenzene or 1, 3 - dimethylbenzene CH3 H 6 C C 1 C H H C 2 5 C 4 CH3 C 3 H para-dimethylbenzene or 1, 4 - dimethylbenzene MD H 6 C C 1 C H H C 2 5 C 4 MD C 3 H para-docs or paradox MD H 6 C C 1 C MD H C 2 5 C H 4 C 3 H ortho-docs or orthodox Fe2+ Fe2+ 6 C C 1 C Fe2+ Fe2+ C 2 5 C 4 Fe2+ C 3 Fe2+ ferrous wheel or ferris wheel NO2 H C C C NO2 H C C H C H o - dinitrobenzene or 1, 2 - dinitrobenzene NO2 CH3 C C C H O2N C C H C NO2 2,4,6 - trinitrotoluene or TNT CH3 CH3 Cl C C Toluene C Cl H C C Cl C H 2, 4, 6 -trichloromethylbenzene or 2, 4, 6 - trichlorotoluene O O C CH3 H C C C COOH H C C H C H 2-acetyloxybenzoic acid or (acetylsalicylic acid or aspirin) H H C C C H C H C C Cl C H H C CClCl Cl C 3 C C Cl H H dichlorodiphenyltrichloroethane or DDT C C C H Cl CH CH2 H C C C H H C C H C H n phenyl ethene or poly styrene aka (styrofoam) Carboxylic Acids COOH O R– - COOH C – OH COOH CH3CHCH2CH2COOH Br 4-Bromopentanoic acid Benzoic acid NO2 p-Nitrobenzoic acid CH2CH2COOH Cl 3-Chloropropanoic acid Classes of Organic Compounds Class of Compound halocarbon Functional Group F, Cl, Br, I alcohol General Formula R X R OH OH ether aldehyde ketone O R O R’ O O C R C O O C R C O carboxylic acid C amine amide C R’ O OH R C OH O O ester H O NH2 O C NH2 R C OR’ R NH2 O R C NH2 Example CH3Cl chloromethane CH3CH2CH2OH 1-propanol CH3OCH2CH3 methoxyethane O CH3CH2CH propanal O CH3CCH3 propanone O CH3CH2COH propanoic acid O CH3COCH3 methylethanoate CH3CH2CH2NH2 propanamine O CH3CH2CNH2 propanamide Organic Nomenclature Flow Chart Functional Groups Functional Groups Timberlake, Chemistry 7th Edition, page 403 Order of Priority of Functional Groups Order of priority Functional group Formula Order of priority Functional group Formula 1 Carboxylic acid -COOH 8 Ketone -CO 2 Sulfonic acid -SO3H 9 Alcohol -OH 3 Ester -COOR 10 Phenol -OH 4 Acid chloride -COCl 11 Thiol -SH 5 Amide -CONH2 12 Amine -NH2 6 Nitrile -CN 13 Ether -OR 7 Aldehyde -CHO 14 Sulfide -SR Selinger, Chemistry in the Marketplace, 1994, page 23 Esters O R – C – O – R’ H H O H C C C O CH H 3 from propanoic acid methyl group H H an ester a carboxylic acid propanoic acid An ester is similar to a carboxylic acid, but the acidic hydrogen has been replaced by an alkyl group methyl propanoate Naming Esters O R – C – O – R’ Name the following ester: O CH3CH2CH2COCH2CH3 Step 1) the ester alkyl group (R’) = ethyl Step 2) the acid (R) = butanoic acid Step 3) the name = ethyl butanoate Formation of an Ester H H H O H C C C C O OH H + Ester Ester Lab I Lab II H H HO C C H H H H butyric acid (butanoic acid) H H ethyl alcohol + water ethyl butyrate (tastes and smells like pineapple) D Ketone H O H H H H C C C C C H 1 H 2 3 4 5 O R C R' H H H 2-pentanone C5H10O Ester H H O H H C C C O C H 2 3 H H 3 carbons = propane 1 O R C O R' H R' methyl propanoate 1) Name the R' first (R' = methyl) 2) Find carbon chain and include the carbonyl carbon. 3) Drop the ending and add -yl C 4 H 8 O2 O Ester CH3 O H C O C CH3 Raspberry R C O R' H H O CH3 H C C O CH2 CH2 C CH3 H CH3 Banana H O H C C O CH2 (CH2)6 CH3 H PP Ester Lab Orange Ester H O O H C C O CH2 CH2 CH3 H R C O R' Pear H H C H O C H C C O CH2 C H Peach C H C H C H Carboxylic acid H O R C H C H OH H H H C C 5 4 H H H C 3 H O C C 2 H 1 OH 3-methylpentanoic acid C6H12O2 Ether R O R' H H H H H H H C C O C C C C H H H H H H H ethyl butyl ether (common name) or ethoxybutane (IUPAC) C6H14O Alcohol 3-ethyl-3-hexanol H R OH H C H H C H H H H H H C C C C C H H H H H C H H C8H18O OH Carboxylic acid O R C H H OH O C C H OH ethanoic acid C 2 H 4 O2 Alcohol H H H R OH HO C C C OH H H H 1,3-propanediol C 3 H 8 O2 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 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 Write a correct IUPAC (or common name) for the following: a. CH3CH2Br b. Cl Cl bromoethane (ethyl bromide) 2,3-dichlorobutane Cl CH3CHCHCH3 c. chlorocyclopentane Cl Br d. CH3CH2CHCH2CHCH3 e. 2-bromo-4-chlorohexane Cl F 1-chloro-1-fluorocyclobutane 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 F F H C C H F H 1,1,1-trifluoroethane C2H3F3 H H C C H 3C CH3 cis-2-butene C 4H 8 H H H H H H H C C C C C C C H H H H H H H 1-heptyne C7H12 H H H H H H H H C H H C C C C C C C H H H H H H H H H H H H C C Cl H H C C C Br H Cl H H H C C H H C H H C C H Chirality: Chiral vs. Achiral right shoe left mitt Chiral right-handed scissors glass plate Achiral tennis racket Chirality H mirror H H H Cl Cl Br Cl I Timberlake, Chemistry 7th Edition, page 484 Br I Br Cl Br I I “cis” and “trans” isomers Geometric Isomers H H3C C=C H C=C CH3 H3C H cis-2-butene (same side) Timberlake, Chemistry 7th Edition, page 414 trans-2-butene (opposite side) CH3 H Geometric Isomers Isomerism trans cis Stereoisomers (Structural Isomers) mirror images Polymers monomer Jaffe, New World of Chemistry, 1955, page 603 homo chain polymer monomer copolymer Copyright © 2007 Pearson Benjamin Cummings. All rights reserved. Polymerization Polymers = Monomer + Monomer + … Synthetic Polymers – – – – Nylon “plastics” Vulcanized rubber polyethylene Natural Polymers – Silk – Proteins (amino acids) – Starch (sugars) Polymers H2C = CH2 – CH2 – CH2 – CH2 – CH2 – Ethene (ethylene) Polyethylene Cl H2C = CH Chloroethene (vinyl chloride) Cl Plastic bottles, film, insulation material Cl – CH2 – CH – CH2 – CH – Polyvinyl chloride (PVC) Plastic pipes and tubing, garden hoses, garbage bags Polymers CH3 CH3CH = CH2 Propene (propylene) CH3 – CH2 – CH – CH2 – CH – Ski and hiking clothing, carpets, artificial joints Polypropylene F F F–C=C–F Tetrafluoroethene F F F F –C–C–C–C– F F F Teflon F Nonstick coatings Polymers Cl H2C = C – Cl 1,1 Dichloroethene Cl Cl – CH2 – C – CH2 – C – Cl Plastic film and wrap Cl Saran H2C = CH Phenylethene – CH2 – CH – CH2 – CH – Polystyrene Plastic coffee cups and cartons, insulation Slime PVA + PVA + PVA – With cross-linking agent (borax solution) What are some things you think of when I say organic? • • • • • • • Medicine Plastics Soil Soap Petroleum Grass Clothing PRISM fellow: Mr. Kevin J. Hodel • • 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 Diamonds PRISM fellow: Mr. Kevin J. Hodel Graphite PRISM fellow: Mr. Kevin J. Hodel 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 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 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 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 Common Polymers • Polystyrene foam can be made into cartons to protect eggs or into packing “peanuts” to cushion fragile objects for shipping. – CH2 – CH – CH2 – CH – Plastic coffee cups and cartons, insulation Polystyrene • Polyethylene: You probably see polyethylene every day! It’s the plastic used to make many containers, among other things. – CH2 – CH2 – CH2 – CH2 – Polyethylene Plastic bottles, film, insulation material • Water-resistant paints and varnishes derive from a family of synthetic polymers called acrylics. PRISM fellow: Mr. Kevin J. Hodel Recycling • Before: Milk jug. After: Picnic table. • Before: Bread bag. After: Trash can. • Before: Sandwich box. After: Frisbee. PRISM fellow: Mr. Kevin J. Hodel Copyright © 2007 Pearson Benjamin Cummings. All rights reserved. Addition Reactions H H C C H + H–H Ni H H H H C C H H H H C C H H H H Br + Br – Br Ni H C C Br H H Acid-Catalyzed Hydration H H C C H H H + H – OH H2SO4 H H H H OH water ethene C C ethanol Write out the mechanism for the formation of isopropyl alcohol (used as rubbing alcohol), from propene. H H C C H H H + H – OH H ethene H2SO4 H C C OH H water ethanol H 180o Molecular Geometry 109.5o Trigonal planar Linear Tetrahedral 107.3o Trigonal pyramidal 104.5o Bent H2O CH4 AsCl3 AsF5 BeH2 BF3 CO2 Order of Priority of Functional Groups Order of priority Functional group Formula Order of priority Functional group Formula 1 Carboxylic acid -COOH 8 Ketone -CO 2 Sulfonic acid -SO3H 9 Alcohol -OH 3 Ester -COOR 10 Phenol -OH 4 Acid chloride -COCl 11 Thiol -SH 5 Amide -CONH2 12 Amine -NH2 6 Nitrile -CN 13 Ether -OR 7 Aldehyde -CHO 14 Sulfide -SR Selinger, Chemistry in the Marketplace, 1994, page 23