1. Chapter 12 Organic Chemistry: The Infinite Variety of Carbon Compounds

2. Organic Chemistry Chemistry of carbon-containing compounds
Most of these come from living things
Not necessarily the case
~30 million chemical compounds known
95% are compounds made of carbon
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3. Carbon Able to bond strongly to other carbon atoms
Forms long chains
Very few other atoms can form short chains, let alone long chains
Capable of forming ring structures
Bonds strongly to other elements
In particular, H, O, and N
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4. Hydrocarbons Made of carbon and hydrogen Several classes Alkanes
Contain only single bonds
Saturated hydrocarbons
Each C atom bonded to maximum number of H atoms
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5. Alkanes Chemical formula CnH2n+2 n = 1, 2, 3, …
CH4, methane, simplest one
C2H6, ethane
All have –ane ending
Follow a pattern
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6. Condensed structural formulas
Show how many hydrogens are attached to each carbon
CH3-CH3 for ethane
Structural formulas show how atoms are bonded together
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7. Isomerism
Isomers: compounds with same molecular formula but different structural formulas
Differences in structure may give rise to differences in chemical and physical properties
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8. Number of possible isomers increases rapidly with the number of carbons
C30H62 – >4 billion possible isomers
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9. Chapter 9

10. Properties of Alkanes
Main property: will burn
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11. Cyclic Hydrocarbons Carbon atom chains in form of rings
Can be represented by structural formulas or symbolic representations
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12. Unsaturated Hydrocarbons
Can have more hydrogen atoms added
Very important in biological systems
Alkene: hydrocarbon that contains one or more carbon-to-carbon double bonds
General formula of CnHn
Simplest: ethylene, C2H4
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13. General formula of CnH2n–2 Simplest: acetylene, C2H2
Alkyne: hydrocarbon that contains one or more carbon-to-carbon triple bonds
General formula of CnH2n–2
Simplest: acetylene, C2H2
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14. Properties of Alkenes and Alkynes
Similar physical properties to alkanes
Undergo more reactions than alkanes
Addition reaction: add compounds across double bond
Importantly, they can form polymers
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15. Aromatic Hydrocarbons
Contain double or triple bonds, but do not show the same reactivity as other unsaturated hydrocarbons
Benzene: C6H6
Used mainly as solvents
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16. Chlorinated Hydrocarbons
Add Cl to hydrocarbons
Increase reactivity of alkanes
Dissolve fats, oils, and greases
Useful for dry cleaning
Tend to accumulate in fatty tissues
If toxic, this will be a problem
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17. Chlorofluorocarbons and Fluorocarbons
Tend to be either liquids or gases
Completely inert
Except in upper atmosphere
O2 soluble in fluorinated compounds
Temporary substitute for hemoglobin
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18. Functional Groups
Group of atoms that gives a family of organic compounds its characteristic chemical and physical properties
Alkyl group: derived from alkane by removing a H
R stands for alkyl group in general
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19. Chapter 9

20. Alcohol Family –OH group Replace -e with -ol CH3OH, methanol, simplest
Produced industrially
Mainly a chemical intermediate
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21. Made industrially and by fermentation
C2H5OH, ethanol
Made industrially and by fermentation
Industrially produced alcohol has noxious substances added
Small, simple alcohols tend to be toxic
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22. Multifunctional Alcohols
Several common alcohols have more than one –OH group
Ethylene glycol: main ingredient in antifreeze
Glycerol: used in lotions
Ingredent in some explosives
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23. Phenol –OH group on benzene ring First antiseptic
Different chemical properties than other alcohols
Behaves more like an acid
First antiseptic
Also causes skin irritation
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24. Ethers Two alkyl groups attached to same O Used mainly as solvent
Example CH3CH2-O-CH2CH3
Used mainly as solvent
Little chemical reactivity
Insoluble in water
Highly flammable
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25. Chapter 9

26. Aldehydes and Ketones Both contain carbonyl group (C=O)
Aldehyde: R-CHO
Ketone: R-CO-R’
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27. Common Aldehydes Change -e ending to -al
Produced by oxidation of alcohols
Formaldehyde – used as a preservative
Larger ones used as fragrances
Benzaldehyde – flavor in maraschino cherries
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28. Common Ketones Change -e ending to -one Acetone most common ketone
Used primarily as a solvent
Produced by oxidation of alcohols
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29. Chapter 9

30. Carboxylic Acid Contains C=O and –OH group on same carbon
Change -e to -oic acid
Acetic acid: acid in vinegar
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31. Chapter 9

32. Esters Derived from carboxylic acids and alcohols Tend to be fragrant
Methyl butyrate apple
Ethyl butyrate pineapple
Ethyl formate rum
Methyl salicylate wintergreen
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33. Amines Contain N May have 1, 2, or 3 alkyl or aromatic groups
Most biological amines are amino acids
Building blocks of proteins
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34. Amides N bonded directly to carbonyl group
Linkage that holds proteins together
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35. Heterocyclic Compounds
Ring compounds that have something other than C in the ring
Occur in plants
Alkaloids: basic in solution
Examples: caffeine, morphine, cocaine
Form basic structure of DNA
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