Organic chemistry

1. ORGANIC
CHEMISTRY
Structures,
Hydrocarbons,
Halides

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

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

4. 1. Nonelectrolytes (do
not conduct
electricity)
2. React slowly
because they are
covalent (nonmetal
+ nonmetal)
3. Usually low melting
point and boiling
point
4. Insoluble and
immiscible in water
PROPERTIES OF
ORGANIC
COMPOUNDS

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

6. 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 =

7. 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

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

9. 1. 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

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

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

12. 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

13. How can we name hydrocarbons? -
IUPAC
Steps in naming simple (unbranched)
hydrocarbons:
1. How many carbon atoms are in the longest
continuous chain? Find the prefix for this from
Table P.
2. If it is an alkane, simply add the suffix “-ane” to
the name.

14. 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.

15. 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.

19. 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

20. 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)

21. What are isomers?
Pentane Isomers

22. Aim # 4 How can we name & draw
substituted hydrocarbons?
1. Count the longest parent chain of carbon atoms – name
that chain
2. Scan the chain and take note of anything that is not a C or
H
3. Indicate the lowest number carbon that has the substitution
4. 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)

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

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

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

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

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

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

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

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

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

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

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

34. 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

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

36. Fluoromethane
1, 2 dibromo ethane
Chloromethane

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

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

39. Aldehydes
a) CHO group found at the end of the hydrocarbon
chain
b) Soluble and reactive
c) Has the suffix “-al”

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

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

42. Amine
a) Nitrogen is present
b) Used in dyes, found in proteins,
DNA
c) Has the suffix -amine

43. Amide
propanamide
a) Contains
b) Used in dyes
c) Has the suffix -amide

44. Ether
Dimethyl ether
Methyl ethyl 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”

45. Aromatic Hydrocarbons
a) 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

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

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

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

49. 3. Addition
a. 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

50. 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

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

52. Fermentation
• Glucose yields ethanol and CO2

53. Polymerization
5CH2=CH2 → ( CH2-CH2 ) 5
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
Condensation Polymerization:
• Creation of a polymer plus water as a product
When an unsaturated hydrocarbon called a monomer(one unit), bonds
itself in long chains creating a polymer(many units)