The Chemistry of Carbon

The Chemistry of Carbon
Organic Chemistry The Chemistry of Carbon “ Carbon is a remarkable element. It exists as the element in two very different forms: soft black graphite and sparkling diamonds. It also forms a vast number of compounds. Organic chemistry was originally a term for the study of compounds found only in living things; now it is more widely seen as the chemistry of carbon compounds, except for a few simple compounds such as carbon dioxide and the carbonates, which include marble and limestone. For a long time, it was believed that such compounds had some hidden “vital force,” and so the chemist could not make them without the aid of a plant or animal. This vital force theory received a blow in 1828 when Friedrich Wohler ( ) obtained urea, a known organic compound, by heating ammonia with cyanate, usually considered an inorganic compound of carbon. As he had prepared cyanate from animal horn, an organic material, a question mark remained about his findings.” The Organic Chemist Marcellin Berthelot ( ) prepared many organic compounds from inorganic compounds or elements. He demonstrated that plants and animals are not unique as the only source s of organic compounds. His work in this field finally disproved the vital force theory. Eyewitness Science “Chemistry” , Dr. Ann Newmark, DK Publishing, Inc., 1993, pg 48 The Chemistry of Carbon

Table of Contents ‘Organic Chemistry’
Alkenes & Alkynes Cycloalkanes Benzene Aromatic Hydrocarbons Carboxylic Acids Classes of Organic Compounds Chirality Polymers Distilling Crude Oil Methane Ethane Propane Butane Pentane Alkanes Alcohols Aldehydes and Ketones Ethers Functional Groups What you should learn: Organic molecules generally bond in regular, predictable ways that allow for a systematic naming and identification of physical and chemical properties. Just like, inorganic chemistry, electron arrangement allows one to predict chemical and physical properties. More Specifically...: State that organic chemistry is the study of carbon - the compounds it forms and the reactions it undergoes Classify compounds as organic or inorganic Describe the carbon-carbon bond Identify and name alkanes, alkenes, and alkynes using a prefix to describe the length of the carbon chain. Define saturated and monounsaturated and polyunsaturated State that functional groups determine the properties of carbon compounds. Recognize the following functional groups a. Alcohols b. Amines Carboxylic acids Define biochemistry as the study of chemistry that occurs in living organisms. Characterize biologically important monomers in terms of their functional groups a. Sugars b. Amino acids c. Fatty acids d. Nucleotides Describe dehydration reactions Petroleum List uses for petroleum other than energy Describe how distillation works in refining petroleum Define octane and explain why octane rating in gasoline is important Explain why the burning of fossil fuels is believed to contribute to pollution

World of Chemistry The Annenberg Film Series
VIDEO ON DEMAND Episode 21 – Carbon Organic chemistry is the study of carbon compounds. The versatility of carbon’s molecular structures provides the enormous range of properties of its compounds. Video 21: Carbon The versatility of carbon's molecular structures and the enormous range of properties of its compounds are presented. (added 2006/10/08) World of Chemistry > Journey through the exciting world of chemistry with Nobel laureate Roald Hoffman as your guide. The foundations of chemical structures and their behavior are explored through computer animation, demonstrations, and on-site footage at working industrial and research labs. Distinguished scientists discuss yesterday’s breakthroughs and today’s challenged. Produced by the University of Maryland and the Educational Film Center. Released on cassette: Fall The Annenberg/ / CPB Collection LEARNER

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
The Chemistry of Carbon “ Carbon is a remarkable element. It exists as the element in two very different forms: soft black graphite and sparkling diamonds. It also forms a vast number of compounds. Organic chemistry was originally a term for the study of compounds found only in living things; now it is more widely seen as the chemistry of carbon compounds, except for a few simple compounds such as carbon dioxide and the carbonates, which include marble and limestone. For a long time, it was believed that such compounds had some hidden “vital force,” and so the chemist could not make them without the aid of a plant or animal. This vital force theory received a blow in 1828 when Friedrich Wöhler ( ) obtained urea, a known organic compound, by heating ammonia with cyanate, usually considered an inorganic compound of carbon. As he had prepared cyanate from animal horn, an organic material, a question mark remained about his findings.” The Organic Chemist Marcellin Berthelot ( ) prepared many organic compounds from inorganic compounds or elements. He demonstrated that plants and animals are not unique as the only source s of organic compounds. His work in this field finally disproved the vital force theory. Eyewitness Science “Chemistry” , Dr. Ann Newmark, DK Publishing, Inc., 1993, pg 48 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
Petroleum - complex mixture of several thousand organic compounds, including straight-chain alkanes, cycloalkanes, alkenes, and aromatic hydrocarbons that contain anywhere from four to several hundred carbon atoms • Gasoline — converted from petroleum in three steps: 1. Distillation — separates compounds on the basis of their relative volatility, which is inversely proportional to their boiling points 2. Cracking — process used to transform the less-volatile, lower-value fractions to more-volatile, higher-value mixtures that have controlled formulas 3. Reforming — second process used to increase the amounts of valuable products; it is the chemical conversion of straight-chain alkanes to either branched-chain alkanes or mixtures of aromatic hydrocarbons Octane ratings – Indicates quality of a fuel – A measure of a fuel’s ability to burn in a combustion engine without knocking or pinging – Octane scale — uses a standard test engine and two pure compounds, n-heptane (which causes a great deal of knocking upon combustion and assigned an octane rating of 0) and isooctane (a very smooth-burning fuel and assigned an octane rating of 100). A gasoline that performs at the same level as a blend of 89% isooctane and 11% n-heptane is assigned an octane rating of 89. Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 429

http://images. google. com/imgres. imgurl=http://static. howstuffworks

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

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

American Petroleum Usage
A Lesson in Economics 1 Barrel of Petroleum 93% Energy Marketplace (42 gallons) 7% Materials Marketplace 42 Gallons of Crude Petroleum 36 Gallons Fuel 36 Gallons Fuel 19 Gallons Gasoline (11 Gallons in 1920) At $3.00 per gallon $108.00 The lesson...burning of oil for fuel may not be the best use. In the past we cut down trees to burn and could have made fine furniture from the wood. The farmer receives very little money for his corn; sells it to Battle Creek, MI where "Tony the Tiger" turns it into breakfast cereal and sells it for $3.50/box. The cereal contains $0.25 in corn and $0.30 in sugar. A federal investment of alternative energy sources is needed. Build an infrastructure of hydrogen fuel cell filling stations. OR 7% (3 Gallons Crude) 100 Nylon Shirts At $20.00 per shirt $ 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. Fritz London Boiling points of simple hydrocarbons in degrees Kelvin C5H12 C4H10 C3H8 C2H6 CH4 C8H18 Molecular Weight 50 100 150 200 250 300 350 400 Temperature (Kelvin) London forces increase with the size of the molecules.

London Forces in Hydrocarbons
Boiling points of simple hydrocarbons in degrees Kelvin C5H12 C4H10 C3H8 C2H6 CH4 Simple hydrocarbons have only London dispersion forces as intermolecular forces C8H18 Molecular Weight 50 100 150 200 250 300 350 400

Methane

CH4 C H C H molecular molecular structural formula shape formula
ball-and-stick model tetrahedral shape of methane tetrahedron

Methane is Tetrahedral
C

Methane is Tetrahedral
Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 634

Methane CH4 C H molecular formula structural formula molecular shape
ball-and-stick model C H H 109.5o C CH4

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

Ethane

Lewis structure of Ethane

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

Ball and Stick model of Ethane

Propane

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

Butane

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

Ball and Stick Models Ethane C2H6 Propane C3H8
Timberlake, Chemistry 7th Edition, page 366

Hydrocarbons

First Ten Hydrocarbons
Number of Carbon Atoms Molecular Formula Condensed Structural Formula Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane 1 2 3 4 5 6 7 8 9 10 CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

Hydrocarbons (alkanes)

First Ten Hydrocarbons
Number of Carbon Atoms Molecular Formula Melting Point, oC Boiling Point, oC # of Isomers 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 CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 -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 2 3 5 9 18 35 75

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

Increasing mass and boiling point
Methane 16 g/mol -161.5oC Ethane 30 g/mol -88.6oC 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 2 3 4 5 6 7 8 9 10 Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 ____ C2H4 C3H6 C4H8 C5H10 C6H12 C7H14 C8H16 C9H18 C10H20 _______ Ethene Propene Butene Pentene Hexene Heptene Octene Nonene Decene _______ Ethyne Propyne Butyne Pentyne Hexyne Heptyne Octyne Nonyne Decyne ____ C2H2 C3H4 C4H6 C5H8 C6H10 C7H12 C8H14 C9H16 C10H18

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.)

C H H C Methane CH4 Butane C4H10 C H ? H C R R Methyl -CH3 Butyl -C4H9

Naming Alkanes 1. Find the longest continuous chain of carbon atoms in the molecule 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 Gas lighters Butane: C4H10 H H H H H - C - C - C - C - H
Butane Gas lighters Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 107

Structural Isomers of C4H10

Isomers of Butane C H C H butane C4H10 methyl propane or isobutane

C4H8 IUPAC name but-1-ene cis-but-2-ene trans-but-2-ene
2-methylpropene

Pentane C5H12

Isomers of Pentane C5H12 These are called structural isomers.

H C H H H H H C C C C H H H H H C H Butane C4H10 1-butene but(1)ene
H H H H Butane C4H10 1-butene but(1)ene n-butene C H Butene C4H8 Butane C4H8 2-butene

H H CH3 H C C C C CH3 H H C H H C H H C H H 3, 3 dimethyl hexane
4 5 6 1 2 3 4 5 6 C CH3 H H C H H C H H C H H 3, 3 dimethyl hexane Lowest sum of numbers is correct or 4, 4 dimethyl hexane

CH3CHCH2CHCH3 C CH3 C7H16 C H H 2, 4-dimethyl pentane
molecular formula H C condensed structural formula Heptane shorthand

H C H C H H H H H C Br Cl C C H C H

H C 2 - methylbutane butane

C H 1, 4 - pentadiene

H C Cl 3 - chloro 1 - propyne

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

Structural Isomers: Pentane (C5H12)
2-methylbutane 2,2-dimethylpropane

Structural Isomers: Hexane (C6H14)
2,3-dimethylbutane 2-methylpentane 2,2-dimethylbutane 3-methylpentane

Structural Isomers: Heptane (C7H16)
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
(Same formula, different structure) C5H12 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

5. 3-ethyl-2,4,5-trimethylheptane 6. 6-ethyl-2,7-dimethylnonane

7. 8. 2,3,4-trimethylhexane 4-ethyl-3-methylheptane 10. 9. 5-tert-butyl-4-isopropyl-3-methyloctane 3,3,4-trimethylhexane

11. 2,2,3-trimethylheptane 12. 6-ethyl-2-methyl-5-propylnonane

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

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

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

H C 3,4-dimethyl octane

CH3 C CH2 Cl H3C H 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 Philips screwdriver bit drum sander Twist hole saw bit

Alcohols

Alcohols (R-OH) Methanol (methyl alcohol) Ethanol (ethyl alcohol)
R = -CH ‘methyl’ R = -CH2CH3 ‘ethyl’ Timberlake, Chemistry 7th Edition, page 437

Primary, Secondary, Tertiary Alcohols
Primary (1o) Alcohol Secondary (2o) Alcohol Tertiary (3o) Alcohol Carbon attached to OH group R1 OH H C R1 OH H R2 C R1 OH R3 R2 C Alkyl group Examples: CH3 OH H C CH3 OH H C CH3 OH C 1o 2o 3o (One alkyl group) (Two alkyl groups) (Three alkyl groups)

Aldehydes and Ketones

Aldehydes and Ketones Aldehyde R-C-H Ketone R-C-R' O O Acetaldehyde
(CH3CH) ethanal, ethyl aldehyde O Formaldehyde (CH2O) methanal Acetone (CH3COCH3) dimethyl ketone, 2-propanone Timberlake, Chemistry 7th Edition, page 453

Ethers

Dimethyl Ether Dimethyl ether C2H6O Flammable anesthesia

Functional Groups

R- Functional Groups -CH3 methyl -CH2CH2CH2CH3 butyl CH3CHCH2CH3 H
sec-butyl -CH2CH3 ethyl – CH2 – C – CH3 H CH3 isobutyl -CH2CH2CH3 propyl CH3CCH3 H isopropyl – C – CH3 CH3 tert-butyl

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

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

Alkenes and Alkynes

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

Alkenes and Alkynes Alkene Alkynes Double bonds Triple bonds ethene
A ball-and-stick model of ethene C2H4, the simplest alkene. ethyne (acetylene) A ball-and-stick model of acetylene (IUPAC name ethyne) Timberlake, Chemistry 7th Edition, page 409

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

Aliphatic Hydrocarbons
Alkane Alkene Alkyne Alkadiene General formula CnH2n + 2 CnH2n CnH2n - 2 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 Carbon-carbon bond type all single bonds one double bond one triple bond two double bonds Naming suffix -ane -ene -yne -diene

Hydrogenation (an addition reaction) unsaturated saturated tub (soft)
shortening stick margarine tub (soft) margarine + H2 vegetable oils unsaturated saturated

Cycloalkanes

Cycloalkanes Formula CnH2n Cyclopropane Cyclobutane Cyclopentane
Condensed Structural Formula Geometric Formula Formula CnH2n Name Cyclopropane Cyclobutane Cyclopentane Cyclohexane

Cycloalkanes Formula CnH2n Cyclopropane Cyclobutane Cyclopentane
Condensed Structural Formula Geometric Formula Formula CnH2n Name Cyclopropane Cyclobutane Cyclopentane Cyclohexane Timberlake, Chemistry 7th Edition, page 388

Benzene

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 H C C H C C H H
Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212

Structure of Benzene H H C C

Benzene 3-D VSEPR Diagram

Names of monosubstituted benzene rings
Chlorobenzene Toluene Bromobenzene Phenol Nitrobenzene Styrene

Benzene NO3- Nitrobenzene
Using Computational Chemistry to Explore Concepts in General Chemistry Mark Wirtz, Edward Ehrat, David L. Cedeno* Department of Chemistry, Illinois State University, Box 4160, Normal, IL Mark Wirtz, Edward Ehrat, David L. Cedeno*

Aromatic Hydrocarbons

Cholesterol Compounds

CH3 C C C C ortho C C para meta position number name 1, 2 ortho- (o-)
6 C C 1 C C ortho 5 2 C C 3 4 para meta position number name 1, 2 ortho- (o-) 1,3 meta- (m-) 1,4 para- (p-)

ortho-dimethylbenzene
C H CH3 6 1 5 2 3 4 ortho-dimethylbenzene or 1, 2 - dimethylbenzene

meta-dimethylbenzene
C H CH3 6 1 5 2 3 4 meta-dimethylbenzene or 1, 3 - dimethylbenzene

para-dimethylbenzene
C H CH3 6 1 5 2 3 4 para-dimethylbenzene or 1, 4 - dimethylbenzene

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

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

C Fe2+ 6 1 5 2 3 4 ferrous wheel or ferris wheel

C H NO2 o - dinitrobenzene or 1, 2 - dinitrobenzene

C CH3 NO2 H O2N 2,4,6 - trinitrotoluene or TNT

2, 4, 6 -trichloromethylbenzene
Cl CH3 H Toluene 2, 4, 6 -trichloromethylbenzene or 2, 4, 6 - trichlorotoluene

O H O C CH3 C C H C C COOH C C H H 2-acetyloxybenzoic acid or
(acetylsalicylic acid or aspirin)

dichlorodiphenyltrichloroethane
Cl C C C C C Cl Cl CCl3 C C C C C H H H H dichlorodiphenyltrichloroethane or DDT

H CH CH2 C C H C C H C C H H phenyl ethene or styrene poly n
aka (styrofoam)

Carboxylic Acids

Carboxylic Acids R – C – OH = O R - COOH CH3CHCH2CH2COOH Br CH2CH2COOH
4-Bromopentanoic acid CH2CH2COOH Cl Benzoic acid p-Nitrobenzoic acid 3-Chloropropanoic acid

Classes of Organic Compounds

Classes of Organic Compounds
Class of Compound Functional Group General Formula Example halocarbon F, Cl, Br, CH3Cl chloromethane R X I CH3CH2CH2OH 1-propanol alcohol OH R OH CH3OCH2CH3 methoxyethane ether O R O R’ CH3CH2CH propanal O C O C O aldehyde R H CH3CCH3 propanone O C O C O ketone R R’ CH3CH2COH propanoic acid O C O OH C O OH carboxylic acid R C O C O CH3COCH3 methylethanoate O ester R R’ CH3CH2CH2NH2 propanamine amine NH2 R NH2 C O NH2 C O NH2 CH3CH2CNH2 propanamide O amide R

Organic Nomenclature Flow Chart

Functional Groups

Functional Groups Timberlake, Chemistry 7th Edition, page 403

Order of Priority of Functional Groups
Formula Functional group Formula Carboxylic acid -COOH Sulfonic acid -SO3H Ester -COOR Acid chloride -COCl Amide -CONH2 Nitrile -CN Aldehyde -CHO Ketone -CO Alcohol -OH Phenol -OH Thiol -SH Amine -NH2 Ether -OR Sulfide -SR Selinger, Chemistry in the Marketplace, 1994, page 23

Esters H O C CH3 H H O H C C C O H H H O R – C – O – R’
an ester H H O from propanoic acid H C C C O H methyl group H H a carboxylic acid propanoic acid The name of an ester consists of two words: (1) the name of the ester alkyl group, and (2) the name of the carboxylic acid with the –ic acid ending changed to –ate. The ester alkyl group is always the group attached to the oxygen, while the carboxylic acid portion is always the portion containing the carbonyl group. An ester is similar to a carboxylic acid, but the acidic hydrogen has been replaced by an alkyl group methyl propanoate

Naming Esters O O R – C – O – R’
Name the following ester: CH3CH2CH2COCH2CH3 Step 1) the ester alkyl group (R’) = ethyl butanoic acid Step 2) the acid (R) = ethyl butanoate Step 3) the name =

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

Ketone H C O R' R C O 1 2 3 4 5 2-pentanone C5H10O

O R C R' H C O methyl propanoate Ester 3 carbons = propane R'
1 2 3 3 carbons = propane R' methyl propanoate 1) Name the R' first 2) Find carbon chain and include the carbonyl carbon. 3) Drop the ending and add -yl (R' = methyl) C4H8O2

H C CH3 O O R C R' H O CH3 H C C O CH2 CH2 C CH3 H CH3 CH2 (CH2)6 H O
Ester O R C R' Raspberry H O CH3 H C C O CH2 CH2 C CH3 H CH3 Banana CH2 (CH2)6 H O C CH3 PP Ester Lab Orange

CH2 H O C CH3 O R C R' H H C C H O H C C O CH2 C C H H C C H H Ester
Pear H H C C H O H C C O CH2 C C H H Peach C C H H

C H C OH O R C OH O H H H C OH O C OH O H C C C C H H H H
Carboxylic acid C H C OH O R C OH O H H H C OH O C OH O H C C C C 1 2 3 4 5 H H H H 3-methylpentanoic acid C6H12O2

ethyl butyl ether (common name)
or ethoxybutane (IUPAC) C6H14O

Alcohol 3-ethyl-3-hexanol H C OH OH R C8H18O

Carboxylic acid C OH O R H O H C C OH H ethanoic acid C2H4O2

Alcohol H C OH HO OH R 1,3-propanediol C3H8O2

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

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

Write a correct IUPAC (or common name) for the following:
a bromoethane (ethyl bromide) b ,3-dichlorobutane c chlorocyclopentane d bromo-4-chlorohexane e chloro-1-fluorocyclobutane CH3CH2Br CH3CHCHCH3 Cl Cl Cl CH3CH2CHCH2CHCH3 Cl Br Cl F

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 H F C C H F H 1,1,1-trifluoroethane C2H3F3

CH3 C H H3C CH3 C H H3C cis-2-butene trans-2-butene C4H8

H C 1-heptyne C7H12

H C H C H H H H H C Br Cl C C H C H

Chirality

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

Chirality mirror H Br I Cl H Cl I Br H Br I Cl H Cl I Br
“A carbon atom’s ability to bond to four other atoms (or groups of atoms) leads to an unusual property. If these four atoms or groups are all different, they can form two distinct molecules that are mirror images of each other. Although chemically identical, two such compounds behave differently when polarized light (where the light waves are in only one plane) is shone through them. They rotate the light in opposite directions and are said to be optically active. The polarimeter was introduced in 1840 to measure the optical activity. Sugars show this property; polarimeters were used routinely to analyze sugar syrups. After the 1860’s, they became valuable tools for collectors of excise duty to determine the strength of sugar solutions for taxation purposes.” - Eyewitness Science “Chemistry” , Dr. Ann Newmark, DK Publishing, Inc., 1993, pg 48 Timberlake, Chemistry 7th Edition, page 484

“cis” and “trans” isomers
Geometric Isomers C = C CH3 H3C H C = C CH3 H3C H cis-2-butene trans-2-butene (same side) (opposite side) Timberlake, Chemistry 7th Edition, page 414

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

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

combustion of hydrocarbons OR compounds w/only
Organic Reactions combustion of hydrocarbons OR compounds w/only C, H, and O: products are… CO2 and H2O Write the equation for the complete combustion of 2-methyl-2-pentene.  C6H O2 9 6 CO H2O 6 O Write the equation for the complete combustion of ethylbutanoate.  C6H12O O2 8 6 CO H2O 6

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. –C–C–H H –C–C–Cl H + HCl + Cl2  If more chlorine is provided, the reaction will produce... –C–C–Cl H + Cl2  –C–C–Cl H Cl + HCl AND SO ON.

Substitution occurs with aromatic compounds, too.
Br + HBr catalyst + Br2 + HCl catalyst + CH3CH2Cl 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.

addition: a multiple bond is broken and two “things” are inserted
–C–C–Br H Br H C=C + Br2 –C–C–Br H H C=C + HBr –C–C–OH H H C=C H2SO4 + H2O H–C–C–C–C–H H –C–C=C–C– Cl H + Cl2

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 H + H2 H C=C catalyst Another addition reaction is polymerization. “lots” of ethylene H C=C –C–C–C–C– H polyethylene

-- One reactant provides an __, the other provides an ___. H OH NO2
condensation (or elimination, or dehydration): _____ is a product Complex protein molecules are made from condensation reactions of amino acids. water -- One reactant provides an __, the other provides an ___. H OH NO2 + HNO3 H2SO4 + H2O CH3CH2OH + CH3OH CH3CH2OH + CH3OH CH3CH2–O–CH3 + H2O alcohol m’c alcohol m’c an ether water

-- Amides can be formed in condensation rxns
between carboxylic acids and amines. Write the equation for the reaction between butanoic acid and nitrogen trihydride. Ammonia is the simplest amine. O OH O NH2 + NH3 + H2O carboxylic acid amine amide water

(the active substance in flavor/odor of pineapple)
Esterification is a condensation reaction between a carboxylic acid and an alcohol. Write the equation for the reaction between butanoic acid and 1-butanol. (the active substance in the characteristic flavor/odor of pineapple) O OH + HO O + H2O butyl butanoate

(the active substance in flavor/odor of cinnamon)
Write the equation for the reaction between 3-phenyl-2-propenoic acid and ethanol. (the active substance in the characteristic flavor/odor of cinnamon) O OH HO + O + H2O ethyl -3-phenyl-2-propenoate “When in doubt, make water.” Mr. B (i.e, ethyl cinnamate )

Amino Acid

NH21- NH3 NH41+ Amine Ammonia Ammonium ion

Polymers

World of Chemistry The Annenberg Film Series
VIDEO ON DEMAND Episode 22 – Polymers How chemists control the molecular structure to create polymers with special properties is explored. Video 22: Age of Polymers How chemists control the molecular structure to create polymers with special properties is explored. (added 2006/10/08) World of Chemistry > Journey through the exciting world of chemistry with Nobel laureate Roald Hoffman as your guide. The foundations of chemical structures and their behavior are explored through computer animation, demonstrations, and on-site footage at working industrial and research labs. Distinguished scientists discuss yesterday’s breakthroughs and today’s challenged. Produced by the University of Maryland and the Educational Film Center. Released on cassette: Fall The Annenberg/ / CPB Collection LEARNER

Polymers homo chain polymer monomer
A representation of the manner in which molecules joint to form long “chain” polymers and copolymers. homo chain polymer monomer Jaffe, New World of Chemistry, 1955, page 603

monomer copolymer

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 – H2C = CH Cl
Plastic bottles, film, insulation material Ethene (ethylene) Polyethylene H2C = CH Cl – CH2 – CH – CH2 – CH – Cl Plastic pipes and tubing, garden hoses, garbage bags Chloroethene (vinyl chloride) Polyvinyl chloride (PVC)

Polymers CH3 CH3CH = CH2 – CH2 – CH – CH2 – CH – F F – C – C – C – C –
Polypropylene CH3 Ski and hiking clothing, carpets, artificial joints Propene (propylene) CH3CH = CH2 – CH2 – CH – CH2 – CH – – C – C – C – C – F F – C = C – F F Nonstick coatings Tetrafluoroethene Teflon

Polymers Cl Cl – CH2 – C – CH2 – C – H2C = C – Cl H2C = CH
Saran Cl 1,1 Dichloroethene H2C = C – Cl Cl Plastic film and wrap Plastic coffee cups and cartons, insulation Phenylethene H2C = CH – CH2 – CH – CH2 – CH – Polystyrene

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 Starch
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. 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. Polystyrene Plastic coffee cups and cartons, insulation – CH2 – CH – CH2 – CH – Polyethylene Plastic bottles, film, insulation material – CH2 – CH2 – CH2 – CH2 – 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

Plastic Resin Codes

Addition Reactions H C H C Ni H – H + Br C H H C Ni Br – Br +

Acid-Catalyzed Hydration
OH H C H2SO4 H – OH + ethene water ethanol Write out the mechanism for the formation of isopropyl alcohol (used as rubbing alcohol), from propene. H H H C H2SO4 + H – OH H C C H OH H ethene water ethanol

Molecular Geometry Trigonal planar Linear Tetrahedral Bent
Trigonal pyramidal H2O CH4 AsCl3 AsF5 BeH2 BF3 CO2

Order of Priority of Functional Groups
Formula Functional group Formula Carboxylic acid -COOH Sulfonic acid -SO3H Ester -COOR Acid chloride -COCl Amide -CONH2 Nitrile -CN Aldehyde -CHO Ketone -CO Alcohol -OH Phenol -OH Thiol -SH Amine -NH2 Ether -OR Sulfide -SR Selinger, Chemistry in the Marketplace, 1994, page 23

Resources - Organic Objectives Functional Groups Quiz
Episode 21 - Carbon Functional Groups Quiz Episode 22 - Polymers Video 21: Carbon The versatility of carbon's molecular structures and the enormous range of properties of its compounds are presented. (added 2006/10/08) World of Chemistry > Video 22: Age of Polymers How chemists control the molecular structure to create polymers with special properties is explored. (added 2006/10/08) World of Chemistry >

The Chemistry of Carbon

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