1. Organic Chemistry

2. Organic compounds Compounds must contain carbon
will also contain hydrogen
may contain oxygen, nitrogen, sulfur and/or phosphorus
There are only ~ 60,000 inorganic compounds
BUT millions of organic compounds

3. HOW?
Carbon has 4 unpaired valence electrons and needs 4 more e- to complete its outer shell.
Carbon makes a total of 4 bonds
Simplest: CH4
Carbon can bond with itself to form chains of many lengths

4. Counting in the language of organic
1 meth
2 eth
3 prop
4 but
5 pent
6 hex
7 hept
8 oct
9 non
10 dec
Organic names directly
related to # of carbons

5. Characteristics of Organics . . .
Forces of attraction
molecules contain covalent bonds
molecules tend to be non-polar
intermolecular attractions tend to be weak
van Der Waals
The longer the molecule is the stronger the forces are

6. So . . .
High vapor pressure
evaporate quickly & have strong odors
low boiling points & melting points when compared to ionic compounds

7. Conductivity Solubility organic molecules do not ionize
do not conduct electricity
Solubility
because organic molecules are non-polar they are soluble in non-polar substances
miscible
insoluble in polar substances
immiscible
Few organic substances
are miscible in water
sugar, acetic acid, alcohols

8. Reactivity Rate of reaction flammable / highly combustible
because of the covalent bonding, reactivity rates tend to be slow
Strong covalent bonding doesn’t allow activated complexes to form easily
random collisions don’t provide enough KE to overcome activation energy.
Many collisions
aren’t effective

9. Different types of formulas
molecular formula
tells you how many of each element are in the molecule
ex. C6H12O6
empirical formula
gives you lowest possible ratio of atoms in the molecule
ex. CH2O

10. structural formula condensed structural
shows the “blueprint” of the molecule
condensed structural
gives a sense of the structure without all the lines
CH2OH(CHOH)4COH

11. Hydrocarbons
Type of organic molecule that contains only hydrogen and carbon
Shapes
straight chain
branched
cyclic
closed
not necessarily circular

13. H-C characteristics Vary greatly in size smallest tend to be gases
largest tend to be solids
As H-C chains become longer the b.p. and m.p. increase due to increased van der Waals forces
Larger molecules are attracted
to each other
(more than smaller molecules)
because they contain more
p+ and e-

14. Sources of fuel: Lowest b.p. gasoline, wax, butane, propane
C1 - C4
methane
ethane
propane
butane
Sources of fuel:
gasoline, wax,
butane,
propane
C4 - C12
octane
C12 - C16
Jet fuel
C16 - C18
Diesel fuel
C18 - C20
C20 - C40
Wax candles
Wax paper
Highest b.p.
C40 +
tar

15. Naming Simple Hydrocarbons
Count the longest continuous chain of Carbons
this is your “parent chain”
use organic “language” as your prefix
meth, eth, prop, but . . .
Determine suffix according to which homologous series it belongs to
alkane or alkene or alkyne

16. Series of Hydrocarbons
Alkanes
contain only single bonds BETWEEN Cs
ane suffix to hydrocarbons
Cn H(2n + 2)
a.k.a. Saturated
every carbon is bonded to 4 other atoms

17. Series of Hydrocarbons
Alkenes
contain a double bond BETWEEN Cs
ene suffix
Cn H2n
Alkynes
contain a triple bond BETWEEN Cs
yne suffix
Cn H(2n-2)
H C C H

18. Alkenes & Alkynes a.k.a. Unsaturated LAST RULE FOR NAMING
multiple bonds between Cs
tend to be more reactive than saturated H-Cs because double and triple bonds easily broken
LAST RULE FOR NAMING
3. Where is the double or triple bond?
Always use the lowest possible number!

19. Practice
Draw the structural formula and/or condensed structural formula & name it
C2H6
C2H4
C3H4
CHCCH2CH2CH3
CH3CH2CHCH2

20. How do you name
more complex
Organic Molecules?
IUPAC
naming system

21. Halogenated H-Cs A halide has been substituted for a H Group 17 Prefix
Fluorine Fluoro-
Chlorine Chloro-
Bromine Bromo-
Iodine Iodo-

22. If a particular halogen appears more than once use prefixes
di -
tri -
A number must also be used to indicate the position of each halogen
Number your parent chain low
BUT a multiple bond gets preference

23. If more than one halogen, name them alphabetically
The complete name
# , # - group name(s) parent name
Dashes between numbers and name
Comma between numbers

24. Practice
CH2BrCH2CH3
CH2FCHFCH2F
CHI2CHBrCH3
CH3CF2CHBrCH2CHCH2

25. Alkyl groups Alkane with one H removed CH4 methane becomes -CH3 methyl
C2H6 ethane becomes -C2H5 ethyl
-C3H7 propyl
-C4H9 butyl
Alkyls form side chains:
must be included in the name with the number of the carbon
it is attached to.

26. If a particular alkyl group appears more than once use prefixes
di -
tri -
Which carbon is it on?
Lowest number C

27. # , # - alkyl name(s) parent name
If more than one ABC’s
The complete name
# , # - alkyl name(s) parent name
Comma between numbers
Dashes between numbers and name

28. Practice CH3CHCH3CH3 CH3CH2CHCH3CH3 CH3(CH2)3CC2H5 CH3CH2CH3
CH3(CH2)3CCH3CH3CHC2H5CH3
3, 4 - diethyl - 2- methylnonane

29. What if you have halogens and alkyl groups????

30. 1,1,1-trichloro-3-methylbutane
WHAT?!!!
H - C - C - C - C - Cl
H H H Cl
| | | |
| | |
H H Cl
H - C - H | H

31. Use the IUPAC naming system
Name the parent chain
Longest continuous chain
NOT NECESSARILY STRAIGHT
H - C - C - C - C - Cl
H H H Cl
| | | |
| | |
H H Cl
H - C - H | H

32. Number the carbons of the parent chain so lowest possible numbers are given to side chains and substitutions
H - C - C - C - C - Cl
H H H Cl
| | | |
| | |
H H Cl
H - C - H | H 4 3 2 1

33. H H H Cl | | | | H - C - C - C - C - Cl | | | H H Cl H - C - H |
1, 1, 1 - trichloro- 1
H - C - C - C - C - Cl
H H H Cl
| | | |
| | |
H H Cl
H - C - H | H
methyl group 3

34. 1,1,1-trichloro-3-methylbutane
Halogen
If more than one….ABC’s
Alkyl
If more than one ABC’s

35. Practice CH3CClClCHC2H5CHCH3CH2CH3 CH3CHCH3CClCH3CH2Br
1,2-dibromo-3-ethyl-2-methylpentane

36. Isomers C4H10 n - butane 2-methylpropane CAN’T just bend the end
same molecular formula
Same # of C, H, O, N . . .
2 or more different structures
C4H10
n - butane
2-methylpropane
CAN’T just bend the end

37. different molecular STRUCTURES they have
Because Isomers have
different molecular STRUCTURES
they have
different chemical & physical properties
m.p., b.p., odor, appearance
reactivity, flammability . . .

38. Practice CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3(CH2)3CH3 n-octane
If your new
structural formula
has a different name . . .
YOU’VE GOT AN ISOMER
CH4
CH3CH3
CH3CH2CH3
CH3CH2CH2CH3
CH3(CH2)3CH3
n-octane
1-butene

39. Organic Reactions X + O2  CO2 + H2O
Combustion
Burning
H-Cs in the presence of O2 (g) will burn to produce CO2 and H2O
X + O2  CO2 + H2O

40. Law of Conservation of Matter
Substitution
When one or more hydrogen atoms of a H-C chain is replaced by a halogen.
C2H6 + Cl2  C2H5Cl + HCl
C2H6 + Cl2  C2H4Cl2 + H2

41. Addition Involves breaking a multiple bond
Unsaturated compounds become more saturated
Alkyne becomes an alkene
Alkene becomes an alkane
C2H2 + Br2  C2H2Br2
C2H4 + Br2  C2H4Br2

42. Polymerization
The process of bonding many small molecules (monomers) together to make a very long chain (polymer)
Water must be a product
Examples of polymers
starches
Proteins
nylon

43. To be continued . . .