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Organic Chemistry The study of carbon, hydrogen, oxygen and nitrogen containing compounds
THE HYDROCARBONS <ul><li>Characteristics </li></ul><ul><ul><li>contain only carbon and hydrogen </li></ul></ul><ul><ul><li...
NOMENCLATURE <ul><ul><li>The number of carbon atoms is determined by the root part of the name </li></ul></ul><ul><ul><ul>...
The Alkanes <ul><li>Characteristics </li></ul><ul><ul><li>saturated hydrocarbons (single bonds only) </li></ul></ul><ul><u...
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 Ethan...
Isomers - molecule has the  SAME  chemical formula, but  DIFFERENT structural formula Butane is the first hydrocarbon to e...
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...
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  ...
Reactions of the Alkanes 1.  Combustion Alkane + Oxygen  Carbon dioxide + Water Ex . CH 4(g)  + 2 O 2(g)   CO 2   (g)  + 2...
The Alkenes -  Unsaturated hydrocarbons <ul><li>Characteristics </li></ul><ul><ul><li>unsaturated hydrocarbons (1 double b...
The Alkenes Isomers - The isomers of the alkene series are identified by the placement of the double bond.  The molecule i...
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
Reactions of the Alkenes 1.  Combustion Alkene + Oxygen Carbon dioxide + Water 2.  Addition  A.  Hydrogen (hydrogenation) ...
The Alkynes -  Unsaturated hydrocarbons <ul><li>Characteristics </li></ul><ul><ul><li>unsaturated hydrocarbons (1 triple b...
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 ...
Reactions of the Alkynes 1.  Combustion Alkyne + Oxygen Carbon dioxide + Water 2.  Addition  A.  Hydrogen (hydrogenation) ...
The Benzene Series  (Aromatic hydrocarbons) The benzene series consists of molecules which are  cyclic  in nature. The gen...
Although it appears that the structure has alternating double and single bonds, the bonding involves  six identical  bonds...
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 ...
The Functional Groups <ul><li>The Alcohols - Characteristics </li></ul><ul><ul><li>Functional Group :  -OH  hydroxyl group...
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 Fermentat...
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...
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...
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) a...
Saponification  - production of soap from the reaction of fatty acid  and a base. Fatty acid + base  soap + glycerine C 3 ...
Organic Acids <ul><li>Characteristics </li></ul><ul><ul><li>contain carboxyl group: -COOH   </li></ul></ul><ul><ul><li>ion...
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  Propan...
Esters <ul><li>Characteristics </li></ul><ul><ul><li>Functional group:  -COO- </li></ul></ul><ul><ul><li>General formula: ...
Naming of the esters: 1- Name the second R group 2- Count the remaining C atoms - name as an alkane,  dropping the  e  and...
Ketones <ul><li>Characteristics </li></ul><ul><ul><li>Functional group: -CO- </li></ul></ul><ul><ul><li>General formula R-...
Aldehydes <ul><li>Characteristics </li></ul><ul><ul><li>Functional group: -CHO </li></ul></ul><ul><ul><li>General formula:...
Ethers <ul><li>Characteristics </li></ul><ul><ul><li>Functional group: -O- </li></ul></ul><ul><ul><li>General formula: R-O...
Amines <ul><li>Characteristics </li></ul><ul><ul><li>Functional group:  N </li></ul></ul><ul><ul><li>General formula: R  N...
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Pp organic 2

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Pp organic 2

  1. 1. Organic Chemistry The study of carbon, hydrogen, oxygen and nitrogen containing compounds
  2. 2. THE HYDROCARBONS <ul><li>Characteristics </li></ul><ul><ul><li>contain only carbon and hydrogen </li></ul></ul><ul><ul><li>non-polar molecules </li></ul></ul><ul><ul><li>low boiling point - decompose easily </li></ul></ul><ul><ul><li>sp 3 hybridization </li></ul></ul><ul><ul><li>insoluble in water (most) </li></ul></ul><ul><ul><li>slow reactivity </li></ul></ul><ul><ul><li>non-electrolytes (poor ionization) </li></ul></ul>
  3. 3. NOMENCLATURE <ul><ul><li>The number of carbon atoms is determined by the root part of the name </li></ul></ul><ul><ul><ul><li>meth 1 carbon </li></ul></ul></ul><ul><ul><ul><li>eth 2 carbon </li></ul></ul></ul><ul><ul><ul><li>prop 3 carbon </li></ul></ul></ul><ul><ul><ul><li>but 4 carbon </li></ul></ul></ul><ul><ul><ul><li>pent 5 carbon </li></ul></ul></ul><ul><ul><ul><li>hex 6 carbon </li></ul></ul></ul><ul><ul><ul><li>hept 7 carbon </li></ul></ul></ul><ul><ul><ul><li>oct 8 carbon </li></ul></ul></ul>
  4. 4. The Alkanes <ul><li>Characteristics </li></ul><ul><ul><li>saturated hydrocarbons (single bonds only) </li></ul></ul><ul><ul><li>homologous series (follow same pattern) </li></ul></ul><ul><ul><li>fewer # of carbons - lower boiling points </li></ul></ul><ul><ul><li>follow same general formula - C n H 2n+2 </li></ul></ul><ul><ul><li>end in -ane </li></ul></ul>
  5. 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. 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. 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. 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. 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.
  10. 10. The Alkenes - Unsaturated hydrocarbons <ul><li>Characteristics </li></ul><ul><ul><li>unsaturated hydrocarbons (1 double bond) </li></ul></ul><ul><ul><li>homologous series (follow same pattern) </li></ul></ul><ul><ul><li>fewer # of carbons - lower boiling points </li></ul></ul><ul><ul><li>follow same general formula - C n H 2n </li></ul></ul><ul><ul><li>end in -ene </li></ul></ul>
  11. 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. 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. 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
  14. 14. The Alkynes - Unsaturated hydrocarbons <ul><li>Characteristics </li></ul><ul><ul><li>unsaturated hydrocarbons (1 triple bond) </li></ul></ul><ul><ul><li>homologous series (follow same pattern) </li></ul></ul><ul><ul><li>fewer # of carbons - lower boiling points </li></ul></ul><ul><ul><li>follow same general formula - C n H 2n-2 </li></ul></ul><ul><ul><li>end in -yne </li></ul></ul>
  15. 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. 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. 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. 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. 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
  20. 20. The Functional Groups <ul><li>The Alcohols - Characteristics </li></ul><ul><ul><li>Functional Group : -OH hydroxyl group </li></ul></ul><ul><ul><li>General Formula : R-OH (R stands for a radical - methyl, ethyl, propyl, etc.) </li></ul></ul><ul><ul><li>Soluble in water (less than 5 C atoms) </li></ul></ul><ul><ul><li>Non-electrolyte: 0% ionization </li></ul></ul><ul><ul><li>Name ends in - ol </li></ul></ul>
  21. 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. 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. 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. 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. 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
  26. 26. Organic Acids <ul><li>Characteristics </li></ul><ul><ul><li>contain carboxyl group: -COOH </li></ul></ul><ul><ul><li>ionize weakly - poor electrolytes </li></ul></ul><ul><ul><li>strong odor </li></ul></ul><ul><ul><li>short chain compounds are soluble in water </li></ul></ul><ul><ul><li>name ends in: -oic acid </li></ul></ul>Structural formula O C O H
  27. 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
  28. 28. Esters <ul><li>Characteristics </li></ul><ul><ul><li>Functional group: -COO- </li></ul></ul><ul><ul><li>General formula: R-COO-R’ </li></ul></ul><ul><ul><li>Artificial odors </li></ul></ul><ul><ul><li>End in - oate </li></ul></ul><ul><ul><li>Formed from esterification reaction </li></ul></ul><ul><ul><ul><li>Acid + alcohol ester + water </li></ul></ul></ul><ul><ul><ul><li>RCOOH + ROH RCOOR’ + H 2 O </li></ul></ul></ul>
  29. 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
  30. 30. Ketones <ul><li>Characteristics </li></ul><ul><ul><li>Functional group: -CO- </li></ul></ul><ul><ul><li>General formula R-CO-R’ </li></ul></ul><ul><ul><li>End in - one </li></ul></ul>Propanone (Acetone) H O H H C C C H CH 3 COCH 3 H H Butanone H H O H H C C C C H C 2 H 5 COCH 3 H H H
  31. 31. Aldehydes <ul><li>Characteristics </li></ul><ul><ul><li>Functional group: -CHO </li></ul></ul><ul><ul><li>General formula: R-CHO </li></ul></ul><ul><ul><li>End in: - al </li></ul></ul>Methanal (formaldehyde) H H C O HCHO Ethanal H H H C C O CH 3 CHO H
  32. 32. Ethers <ul><li>Characteristics </li></ul><ul><ul><li>Functional group: -O- </li></ul></ul><ul><ul><li>General formula: R-O-R’ </li></ul></ul><ul><ul><li>End in: ether </li></ul></ul>Dimethyl ether H H H C O C H CH 3 OCH 3 H H Ethyl methyl ether H H H H C O C C H C 2 H 5 OCH 3 H H H
  33. 33. Amines <ul><li>Characteristics </li></ul><ul><ul><li>Functional group: N </li></ul></ul><ul><ul><li>General formula: R N R” </li></ul></ul><ul><ul><ul><ul><ul><li> </li></ul></ul></ul></ul></ul>

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