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Organic Chemistry Compounds and Reactions
1. Organic Chemistry The study of carbon, hydrogen, oxygen and nitrogen containing compounds
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5. The Alkanes - Saturated hydrocarbons Methane H H C H CH 4 H Propane H H H H C C C H C 3 H 8 H H H Ethane H H H C C H C 2 H 6 H H
6. Isomers - molecule has the SAME chemical formula, but DIFFERENT structural formula Butane is the first hydrocarbon to exhibit isomerism. Naming : 1- find longest chain of C atoms and name it 2- name attached group 3- indicate the address of the attached group with number n- Butane H H H H H C C C C H C 4 H 10 H H H H 2-methyl propane (isobutane) H H C H H H H C C C H C 4 H 10 H H H
7. n-pentane H H H H H H C C C C C H C 5 H 12 H H H H H 2,2-dimethylpropane H (neopentane) H C H H H H C C C H C 5 H 12 H H H C H H 2-methylbutane H (isopentane) H C H H H H H C C C C H C 5 H 12 H H H H
8. n-hexane H H H H H H H C C C C C C H C 6 H 14 H H H H H H n-heptane H H H H H H H H C C C C C C C H C 7 H 16 H H H H H H H n-octane H H H H H H H H H C C C C C C C C H C 8 H 18 H H H H H H H H
9. Reactions of the Alkanes 1. Combustion Alkane + Oxygen Carbon dioxide + Water Ex . CH 4(g) + 2 O 2(g) CO 2 (g) + 2 H 2 O (g) 2. Halogen Substitution One hydrogen from a saturated hydrocarbon is replaced by a halogen atom forming a halogen substituted hydrocarbon. Ex. C 2 H 6 + Cl 2 C 2 H 5 Cl + HCl Two products are always produced.
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11. The Alkenes Isomers - The isomers of the alkene series are identified by the placement of the double bond. The molecule is named by indicating the location (by number) of the double bond. Ethene H H C C C 2 H 4 H H Propene H H H H C C C C 3 H 6 H H
12. 1-butene H H H H C C C C H C 4 H 8 H H H 2-butene H H H H C C C C H C 4 H 8 H H H
13. Reactions of the Alkenes 1. Combustion Alkene + Oxygen Carbon dioxide + Water 2. Addition A. Hydrogen (hydrogenation) - breaks double bond, adds two hydrogen atoms Alkene + Hydrogen Alkane C 3 H 6 + H 2 C 3 H 8 B. Halogen (halogenation) - breaks double bond, adds two halogen atoms Alkene + Halogen Halogen substituted hydrocarbon C 3 H 6 + Cl 2 C 3 H 6 Cl 2
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15. The Alkynes Ethyne (acetylene) H C C H C 2 H 2 Propyne H H C C C H C 3 H 4 H 1-Butyne H H H C C C C H C 4 H 6 H H 2-Butyne H H H C C C C H C 4 H 6 H H
16. Reactions of the Alkynes 1. Combustion Alkyne + Oxygen Carbon dioxide + Water 2. Addition A. Hydrogen (hydrogenation) - breaks triple bond, adds four hydrogen atoms Alkyne + 2 Hydrogen Alkane C 2 H 2 + 2 H 2 C 2 H 6 B. Halogen (halogenation) - breaks triple bond, adds four halogen atoms Alkene + 2 Halogen Halogen substituted hydrocarbon C 2 H 2 + 2 Cl 2 C 2 H 2 Cl 4
17. The Benzene Series (Aromatic hydrocarbons) The benzene series consists of molecules which are cyclic in nature. The general formula is C n H 2n-6 . Benzene H C H C C H C 6 H 6 H C C H C H
18. Although it appears that the structure has alternating double and single bonds, the bonding involves six identical bonds. A resonance structure is used to show structural formula of benzene. H H C C H C C H H C C H H C C H H C C H C C H H An abbreviated structural formula can be used in place of the above: OR
19. Toluene or Methylbenzene C 7 H 8 H C H C C CH 3 H C C H C H An abbreviated structural formula can be used in place of the above: CH 3 CH 3
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21. Monohydroxy Alcohols Methanol H H C O H CH 3 OH H Ethanol H H H C C O H C 2 H 5 OH H H Produced by Fermentation Glucose zymase Carbon dioxide + Ethanol C 6 H 12 O 6 CO 2 + C 2 H 5 OH
22. 1-propanol H H H H C C C OH C 3 H 7 OH H H H The above is a primary alcohol 2-propanol (isopropyl alcohol) H H H H C C C H C 3 H 7 OH H OH H The above is a secondary alcohol. The -OH is attached to a C atom which is attached to two others. 1-butanol H H H H H C C C C OH C 4 H 9 OH H H H H
23. 2-butanol H H H H H C C C C H C 4 H 9 OH H H OH H 2-methyl-2-propanol (tertiary butanol) H H C H H H H C C C H C 4 H 9 OH H OH H Tertiary alcohol - the -OH is attached to a C atom which is attached to three others.
24. Di-hydroxy Alcohols - contain two -OH groups OH OH H C C H C 2 H 4 (OH) 2 H H 1,2-ethanediol (ethylene glycol) anti-freeze Tri-hydroxy Alcohols - contain three -OH groups H H H H C C C H C 3 H 5 (OH) 3 OH OH OH 1,2,3-propanetriol (glycerine or glycerol)
25. Saponification - production of soap from the reaction of fatty acid and a base. Fatty acid + base soap + glycerine C 3 H 5 (C 17 H 35 COO) 3 + 3 NaOH 3 C 17 H 35 COONa + C 3 H 5 (OH) 3
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27. Methanoic Acid O (Formic Acid) H C O H HCOOH Ethanoic Acid H O (Acetic Acid) H C C O H CH 3 COOH H Propanoic Acid H H O H C C C O H C 2 H 5 COOH H H
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29. Naming of the esters: 1- Name the second R group 2- Count the remaining C atoms - name as an alkane, dropping the e and adding - oate Methanol + Acetic Acid Methyl ethanoate + water CH 3 OH + CH 3 COOH CH 3 COOCH 3 + H 2 O Ethanol + Methanoic Acid Ethyl methanoate + water C 2 H 5 OH + HCOOH HCOOC 2 H 5 + H 2 O
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