1. Unit 13 ORGANIC CHEMISTRY

2. Aim #1 What is an organic compound and what are its properties ?
Organic chemistry is the study of carbon and its compounds
found in fossil fuels, plants, animals
Examples include: gasoline, oil, sugars
Hydrocarbon – contains only the elements H & C (TABLE Q)
Therefore, hydrocarbons are organic, but not all organic compounds are hydrocarbons
Anything living is carbon based, chains and rings

3. Why is carbon so special?
Has 4 valence electrons, so it can bond 4 times to achieve a stable octet

4. PROPERTIES OF ORGANIC COMPOUNDS
Nonelectrolytes (do not conduct electricity)
React slowly because they are covalent (nonmetal + nonmetal)
Usually low melting point and boiling point
Insoluble and immiscible in water
PROPERTIES OF ORGANIC COMPOUNDS
Carbon forms 4 covalent bonds
As new developments in medicines fuel formations, new organisms, new organic molecules
Will not dissolve in polar molecules
Solid – soft with low mp and doesn’t dissolve in water
Undergo combustion or react with oxygen to produce CO2 & H2O – basis for energy production (in US electricity generated by burning coal oil or natural gas, cars, motorcycles etc. powered by octane
2C8H18 (l) + 25O2 (aq)  16CO2 (g) + 12H2O(l)
Decompose upon heating in absence of oxygen (to form component elements – crude oil formed)
(inorganic reactons use catalysts – orgo reactions are more prone to error in the lab

5. Which of the following are organic?
Which of the following are hydrocarbons?

6. Types of Chemical Formulas
Molecular Formula- shows the # of atoms of each element in a compound (least informative formula)
Ex. Propane = C3H8

7. Types of Chemical Formulas
Structural Formula- shows the number of atoms of each element AND the arrangement of the atoms; most informative formula
Ex. Propane =

8. Types of Chemical Formulas
Condensed/Collapsed Formula- combination of both structural and molecular formulas
-each carbon is written with its constituent hydrogens followed by the proper subscript
Ex. Propane = CH3CH2CH3

9. Structural Formula
Condensed Formula
CH3C2CH3

10. HOMOLOGOUS SERIES
Table Q shows the general formulas and structures for 3 families of hydrocarbons

11. Alkanes- single bonded hydrocarbons contains ONLY (C-C)
These bonds are considered saturated. They have the maximum number of hydrogens attached.
Remember that each bond represents 1 pair of shared electrons (2 e- total per bond)
General formula: CnH2n+2
Example: Methane

12. 2. Alkenes- double bonded hydrocarbons, contains (C=C)
These bonds are considered unsaturated
General formula: CnH2n
Example: Butene

13. 3. Alkynes – triple bonded hydrocarbons, contains (C- C triple bonds)
These bonds are considered unsaturated
General formula CnH2n-2
Example: Propyne

14. How can we name hydrocarbons? -IUPAC
To name simple hydrocarbons (straight chain, only C and H), we will put information from Table P and Table Q together
Table P shows the prefix to determine how many carbons are in a compound
Ex) Give the prefixes for the following:
C2H6
C4H6
C5H12
C7H14
C8H18
C10H20
International union of pure and applied chemistry
Draw in the structural formula for CH4

15. How can we name hydrocarbons? -IUPAC
Steps in naming simple (unbranched) hydrocarbons:
How many carbon atoms are in the longest continuous chain? Find the prefix for this from Table P.
If it is an alkane, simply add the suffix “-ane” to the name.
International union of pure and applied chemistry
Draw in the structural formula for CH4

16. How can we name hydrocarbons? -IUPAC
3. If it is an alkene, you must first indicate the location of the double bond(s) if the molecule has more than 3 Cs. Do this by numbering the carbons on the chain and stating the lowest carbon # where the double bond is located. Then add the suffix “-ene” to the name.
International union of pure and applied chemistry
Draw in the structural formula for CH4

17. How can we name hydrocarbons? -IUPAC
4. If it is an alkyne, you must first indicate the location of the triple bond(s) if the molecule has more than 3 Cs. Do this by numbering the carbons on the chain and stating the lowest carbon # where the triple bond is located. Then add the suffix “-yne” to the name.
International union of pure and applied chemistry
Draw in the structural formula for CH4

21. Aim # 3 What are isomers?
Isomers have the same molecular formula but are rearranged in a different structure with different chemical and physical properties.
At least 4 carbons must be present in a molecule to have isomers
Methane, ethane, and propane DO NOT have any isomers

22. What are isomers?
Butane is the first molecule to have isomers. The larger the molecule (the more carbon atoms), the more isomers the molecule will have
3 ways to make an isomer:
1. Make a branch (on a non-terminal carbon)
2. Move a branch
3. Move a multiple bond (a double or triple bond)

23. What are isomers?
Pentane Isomers

24. What are isomers?
Pentene Isomers

25. Aim # 4 How can we name & draw substituted hydrocarbons?
Count the longest parent chain of carbon atoms – name that chain
Scan the chain and take note of anything that is not a C or H
Indicate the lowest number carbon that has the substitution
Name the substitution (F-fluoro, Cl-chloro, Br- bromo, I-iodo, CH3- methyl, CH2 - ethyl)
Notice that if there are more than one substitutions, you must indicate all of their locations (which # C they’re attached to), and put a numerical prefix in front of the substitution name (“di-” for 2, “tri-” for 3, “tetra-” for 4)

26. How can we name and draw substituted hydrocarbons?
chloromethane

27. How can we name and draw substituted hydrocarbons?
dichloromethane

28. How can we name and draw substituted hydrocarbons?
F H
H - C – C – H
H H
1-fluoroethane

29. How can we name and draw substituted hydrocarbons?
1,1 -difluoroethane

30. How can we name and draw substituted hydrocarbons?
F H
H - C – C – H
H F
1,2 - difluoroethane

31. How can we name and draw substituted hydrocarbons?
1-fluoro, 1,2 – dibromo ethane

32. How can we name and draw substituted hydrocarbons?
1,2 – dichloropropane

33. How can we name and draw substituted hydrocarbons?
1,3 - dicholoropropane

34. How can we name and draw substituted hydrocarbons?
2-methylpropane

35. How can we name and draw substituted hydrocarbons?
2,2 – dimethyl butane

36. How can we name and draw substituted hydrocarbons?
2, 2, 3 – trimethyl pentane

37. Aim # 5 What are functional groups?
Although hydrocarbons are the most basic organic compounds, many other organic compounds form when other atoms replace one or more hydrogen atoms in a hydrocarbon
These atoms or groups of atoms, called functional groups, replace hydrogen atoms in a hydrocarbon and give the compound distinctive physical and chemical properties
The naming of these compounds is made easy because they derive their names from the hydrocarbon with the corresponding number of carbon atoms

38. Halides- Have one of the halogens as a branched group
F (fluoro)
Cl (chloro)
Br (bromo)
I (iodo)

39. Chloromethane
Fluoromethane
1, 2 dibromo ethane

40. Alcohols Have an –OH group Flammable, soluble
NOT bases (covalently bonded) and NOT electrolytes
Has the suffix “-ol” and must also state the location of the –OH along the carbon chain (using lowest # location)

41. Organic Acids Have a carboxyl group (-COOH) at the last carbon
Also known as carboxylic acids: weak acids/weak electrolytes because they generate H+ ions in solution
Has the suffix “-oic acid”

42. Aldehydes CHO group found at the end of the hydrocarbon chain
Soluble and reactive
Has the suffix “-al”

43. Ketones CO group located on an interior carbon atom
Can NEVER be a terminal carbon, or it would be an aldehyde!
Has the suffix “-one”
Somewhat soluble, needs at least 3 carbons

44. Ester Contains COO connecting parent chain to branch
Smell nice! Found in perfumes, foods
Has the suffix -anoate

45. Amine Nitrogen is present Used in dyes, found in proteins, DNA
Has the suffix -amine

46. Amide
Contains
Used in dyes
Has the suffix -amide
propanamide

47. Ether a) look for –O- somewhere in the middle b) anesthetic, soluble
Dimethyl ether
a) look for –O- somewhere in the middle
b) anesthetic, soluble
c) Name small chain, then the large chain and follow with suffix “-ether”
Methyl ethyl ether

48. Aromatic Hydrocarbons
6 carbons are in a closed ring with alternating double and single bonds
b) Called benzene
c) It is very stable
d) Can be substituted
Methylbenzene
1,4-dichloro benzene

49. Aim # 6 What are the different organic reactions?

50. 1. Combustion In the presence of oxygen:
A hydrocarbon and oxygen produces CO2 and water
In limited oxygen:
A hydrocarbon and oxygen produce CO and Water

51. 2. Substitution CH4 + Cl2  CH3Cl + HCl
Involves a saturated hydrocarbon
One or more H gets replaced by another atom or group
Compare the number of H on the reactant and product side
CH4 + Cl  CH3Cl + HCl

52. 3. Addition
Involves an unsaturated hydrocarbon, atoms/ groups are added in at a multiple bond site.
Unsaturated hydrocarbon  saturated hydrocarbon
b. Hint: look for 2 reactants and one product

53. 4. Esterification An organic acid and alcohol makes an ester and water
Should be able to recognize the acid group and the hydroxyl group in the reactants
Hint: table R to recognize the ester in the products

54. 5. Saponification
A fat reacts with a base to produce and alcohol (look for glycerol) and a soap

55. Fermentation
Glucose yields ethanol and CO2

56. Polymerization 5CH2=CH2 → ( CH2-CH2 ) 5
When an unsaturated hydrocarbon called a monomer(one unit), bonds itself in long chains creating a polymer(many units)
Addition Polymerization:
Unsaturated monomers join by breaking their double or triple bonds to bond with one another, making long chains
Several monomers combine to make the polymer
5CH2=CH2 → ( CH2-CH2 ) 5
Condensation Polymerization:
Creation of a polymer plus water as a product