INTRODUCTION TO ORGANIC CHEMISTRY
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1 INTRODUTION TO ORGANI EMISTRY GENERAL DESRIPTION A. The Study of arbon ompounds B. Organic reminds us of plant or animal origins of some compounds 1. Natural medicines: morphine, penicillin 2. Fibers: cotton, silk, wool 3. Foodstuffs: Fats, arbohydrates, Proteins, Vitamins 4. Natural rubber; Natural gas and petroleum. Man-made Substances also Included 1. Drugs: Xyloaine, Aspirin, Acetaminophen 2. Fibers: Nylon, Dacron, Rayon 3. Other Polymers: Saran, Teflon 4. Man-Made Rubber; Synfuels
2 DIFFERENES BETWEEN ORGANI AND INORGANI OMPOUNDS A. Elemental omposition 1. Inorganic ompounds: All elements present 2. Organic ompounds: arbon and hydrogen predominate B. Types of Bonding 1. Inorganic ompounds: Ionic 2. Organic ompounds: ovalent. Types of Particles which must be onsidered 1. Inorganic ompounds: Ions and Molecules 2. Organic ompounds: Ions and Molecules
3 omparison of Physical Properties of Organic and Inorganic ompounds Salt Ethanol Benzene Formula Nal 26O 66 Melting 804 o -117 o 5 o point Boiling 1413 o 78 o 80 o point Burns? No Yes Yes Water Yes Yes No soluble?
4 UNIQUENESS OF ARBON (Group IV) Intermediate Electronegativity - Favors ovalent Bonds Ability to Form hains (atenation) Ability to Form Multiple Bonds and Rings
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6
7
8 ovalent Bonds Between Atoms in Organic Molecules Single bonds O O
9 ovalent Bonds Between Atoms in Organic Molecules Single bonds O O N N
10 Double Bonds O O
11 Triple Bonds N N
12 STRUTURAL FORMULAS AND ONDENSED STRUTURES A. Because organic compounds are molecular in nature, the additional information conveyed in structural formulas is sometimes necessary. B. Structural formulas show the connections between atoms based on their abilities to form covalent bonds. O N O N N
13 Because carbon and hydrogen are so common, abbreviations are used ( 2 ) 2
14 Example of a ondensed Structure: What does 1122O represent? O ( 2 ) 4 O
15 Abbreviations for yclic Structures N 2 N
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17
18
19 Isomerism, A omplicating Factor in Organic hemistry 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
20 Example #2: 24O2 O O ompound 3 O O 3 Name Acetic Acid Methyl formate Melting point 16.6 o -99 o Boiling point 118 o 31 o Density 1.05 g g/ml 0.97 g/ml
21 LASSES OF ORGANI OMPOUNDS A. YDROARBONS (ONTAIN ONLY ARBON AND YDROGEN) Alkanes Alkenes Alkynes Benzene & derivatives (paraffins) (olefins) (acetylenes) Aliphatic compounds Aromatic compounds Saturated compounds Unsaturated compounds B. NON YDROARBONS
22 NOMENLATURE OF YDROARBONS A. 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.
23 B. Basis of the IUPA System of naming 1. The root name of a compound is derived from the longest continuos chain of carbon atoms or the longest continuous chain of carbon atoms containing a given special structural feature. a. ommon stems are used to indicate the length of carbon chains. meth-, eth-, pro-, but-, pent-, hex-, hept-, oct-, non-, dec-, b. ommon suffixes are use to indicate the class of compounds. Alkane Alkene Alkyne
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25
26 2. 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
27 . 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
28 Parent alkane When attached to another chain Methane (PARENT AIN) Methyl-(BASE NAME) (PARENT AIN) Ethane Ethyl-(BASE NAME) (PARENT AIN) Propane Propyl-(BASE NAME) (PARENT AIN) Isopropyl-(BASE NAME)
29 D. The Position of Attachment to the Parent hain is Indicated by Numbering the Parent hain 1. For carbon chains with double or triple bonds (alkenes and alkynes), the numbering system for the base carbon chain has already been established and does not change. 2. For saturated carbon chains (alkanes) the numbering system for the base carbon chain is determined by the positions of the substituents. E. Substituent names (in alphabetical order) are added (prefixed) to the base name of the compound.
30 Ethylmethylnonane 5-ethyl-4-methylnonane
31 4,5-dimethylnonane
32 Location of Alkyl groups Family 4-isopropyl-3-methylheptane Base name Alkyl groups Longest chain
33
34 2-ethyl-4,5-dipropyl-1-octene
35
INTRODUCTION TO ORGANIC CHEMISTRY
INTRODUTION TO ORGANI EMISTRY GENERAL DESRIPTION OF ORGANI EMISTRY The Study of arbon ompounds GENERAL DESRIPTION OF ORGANI EMISTRY The Study of arbon ompounds Organic Man-made Substances Plant or Animal
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