INTRODUCTION TO ORGANIC CHEMISTRY
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1 INTRODUTION TO ORGANI EMISTRY GENERAL DESRIPTION OF ORGANI EMISTRY The Study of arbon ompounds
2 GENERAL DESRIPTION OF ORGANI EMISTRY The Study of arbon ompounds Organic Man-made Substances Plant or Animal Origins morphine, penicillin Fibers: cotton, silk, wool Fats, arbohydrates, Proteins, Vitamins Natural rubber, Natural gas, petroleum Xyloaine, Aspirin, Acetaminophen Nylon, Dacron, Rayon Saran, Teflon Man-Made Rubber, Synfuels
3 Differences Between Organic and Inorganic ompounds Inorganic Organic Elements Present Metals and Nometals Mostly arbon Bonding ovalent and Ionic Mostly ovalent Particles IONS & molecules ions & MOLEULES Melting Points Relatively igh Relatively Low Boiling Points Relatively igh Relatively Low Electrolytes STRONG to weak weak to NON
4 omparison of Physical Properties of Organic and Inorganic ompounds Name Salt Ethyl alcohol Benzene Formula Nal 26O 66 Organic/Inorganic Inorganic Organic Organic Melting Point 804 º -117 º 5 º Boiling Point 1413 º 78 º 80 º Burns in O2? No Yes Yes Water Soluble? Yes Yes No
5 WY ARBON? Intermediate Electronegativity - Favors ovalent Bonds Ability to Form hains - (atenation) Ability to Form Multiple Bonds and Rings
6
7 Allotropes of arbon
8 ydrocarbons (contain and ) The Simplest lass of Organic ompounds arbon can bond in different ways 4
9 Because carbon and hydrogen are so common, abbreviations are used ( 2 ) 2
10 Structural Formulas and ondensed Structures Example of a ondensed Structure: What does the molecular formula 1122O represent? O ( 2 ) 4 O
11 Remember that structural formulas do not always reflect true 3-D structures
12 ydrocarbons The Simplest lass of Organic ompounds arbon can bond in different ways (multiple bonds) 24 22
13 Structural Formulas and Bond Angles Methane (109.5º angles) 120º 180º
14 Structural Representation of Simple Alkanes
15 Formulas and Properties of Normal Alkanes n Molecular ondensed Name Melting Boiling Formula Structural Formula point ( o ) point ( o ) methane ethane propane butane pentane hexane heptane octane nonane decane
16 Kinds of Attractive Forces Dispersion Forces Temporary polarity in molecules due to unequal electron distribution Dipole Dipole Attractions Permanent polarity in molecules due to their structure ydrogen Bonds An especially strong dipole dipole attraction resulting from the attachment of to an extremely electronegative atom
17 Properties of Straight hain Alkanes NonPolar Molecules
18 Molecular shape and boiling point. more points for dispersion forces to act fewer points for dispersion forces to act
19 1. hoose the Substance in Each Pair with the igher Boiling Point a) b)
20 Physical Properties of Alkanes The Basis for Fractional Distillation
21 Uses of ydrocarbons
22 Isomerism A. A molecular formula may not convey a unique structure. B. Isomers - ompounds with identical molecular formulas, but different structural formulas.. Example #1: 410 ompound Name Butane Isobutane Melting point -138 o -160 o Boiling point 0 o -12 o Density g/ml g/ml
23 Isomerism n-butane butane iso-butane 2-methylpropane
24 Isomerism Another example and
25 NOMENLATURE OF YDROARBONS Why is the IUPA system Necessary? onsider the following carbon hydrides Each formula represents a unique compound If structural formulas (arrangement in space) are considered, 37 has only 1 isomer. 410 has 2 isomers. 512 has 3 isomers. 614 has 5 isomers has 75 isomers has 4 x 10 9 isomers.
26 Basis of the IUPA System of Naming 1. The root name of a compound is derived from the longest continuous chain of carbon atoms or the longest continuous chain of carbon atoms containing a given special structural feature.
27 2. ommon stems used to indicate the length of carbon chains. 3. ommon suffixes used to indicate the class of compounds. Alkane Alkene Alkyne
28 n Molecular ondensed Name Melting Boiling Formula Structural Formula point ( o ) point ( o ) 1 4 methane ethane propane butane pentane hexane heptane octane nonane decane
29 Alkenes
30 Alkynes
31 4. If the carbon chain contains unsaturation (double or triple bonds), the carbon chain is numbered so as to give double or triple bonds the lowest number Butene 2-Butene 3-Butene Butene
32 Substituents may be attached to a carbon chain 1. Substituents which are not pieces of alkanes: F- Fluoro- -NO2 Nitro l- hloro- -N2 Amino Br- Bromo- -O ydroxy I- Iodo- 2. Akyl Substituents - names derived from alkane names 3-, methyl 32-, ethyl 322-, propyl -yl =substituent
33 ethyl-4-methylnonane
34 nonane dimethyl 4,5-4,4- dimethyl nonane
35 ydrocarbon Nomenclature Putting it Together for a Simple Alkane Position of alkyl groups Family 4-isopropyl-3-methyl heptane Base name Alkyl groups Longest chain
36 Nomenclature of Alkenes ethyl -4,5- dipropyl-1-octene
37 ydrocarbon Nomenclature A more complicated example l l 2 l l l 2 l l 3 l 2 2 l 1,3,5-trichloro-5-isobutyl-3,9-dimethyl decane
38 hemical Reactions of ydrocarbons ombustion Reactions
39 ombustion - Burning in Oxygen 8. Propane burns in oxygen to yield carbon dioxide and water O > O2 + 2O 38 +? O > 3 O O O > 3 O O
40 9. ombustion - Burning in Oxygen Butane burns in oxygen to yield carbon dioxide and water O > O2 + 2O 410 +? O > 4 O O ? O > 8 O O O > 8 O O
41 Families of Organic ompounds Alkanes O Aldehydes O Alkenes Ketones Alkynes O O arboxylic Acids Aromatics O O Esters O Alcohols N Amines O O Ethers N Amides
42 Families of Organic ompounds Family General Formula Example Name hydrocarbons propane alcohols R-O O 1-propanol 3 3 O 2-propanol ethers R-O-R 3 O 3 dimethyl ether 3 O 2 3 ethyl methyl ether aldehydes R-O O 3 2 propanal ketones R-(O)-R 2-pentanone 3 O O pentanone
43 Families of Organic ompounds Family General Formula Example Name carboxylic acids R-OO propanoic acid O 3 2 O esters R-OOR methyl propanoate O 3 2 O 3 O ethyl ethanoate 3 O 2 3 amines R-N N 2 propyl amine amides R-(O)-N2 propanamide O 3 2 N O N 3 N-methyl propanamide
44 3 O 3 2 O 2 methyl ether ethylene oxide O propane 3 3 N acetaldehyde acetonitrile
45 methyl ether b.p., 249 K ethylene oxide b.p., 284 K propane b.p., 231 K acetaldehyde b.p., 293 K acetonitrile b.p., 355 K
46 Families of Organic ompounds
47 10. hoose the substance in each pair with the higher boiling point a) 2F2F or 3F2 no net dipole net dipole
48 10. hoose the substance in each pair with the higher boiling point b) or net dipole no net dipole
49 Effect of -Bonding on Boiling Point 11. hoose the substance in each pair that is a liquid at room temperature (the other is a gas) a) 3O 3F2 b) 3-O N2
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