1. The chemistry of carbon and carbon-based compounds
Organic Chemistry
The chemistry of carbon and carbon-based compounds

2. Why is carbon so special?
Carbon is unique among
the elements because: --
it can have up to four bonds per C atom 
single, double, or triple bonds
–C–C–
C=C
–C=C– --
it can form REALLY long chains of C atoms --
its bonds are strong

3. Organic Chemistry Organic Chemistry is everywhere!
Smells & tastes fruits, chocolate, fish, mint
Medications Aspirin, Tylenol, Decongestants, Sedatives
Addictive substances Caffeine, Nicotine, Alcohol, Narcotics
Hormones/Neurotransmitters Adrenaline, Epinephrine
Food/Nutrients Carbohydrates, Protein, Fat, Vitamins
Genetics DNA, RNA
Consumer products Plastics, Nylon, Rayon, Polyester 3

4. Drawing Organic Structures
Shortcuts make structures easier & faster to draw
Butane: C4H10
Lewis Structure
Carbon Atoms
Line Structure
Only shows bonds
C atoms assumed at each end and intersection of bonds
H atoms not shown
Assume 4 bonds to each C
Fulfill C’s 4 bonds by adding H’s
Condensed Structures
CH3CH2CH2CH3
CH3(CH2)2CH3

5. Practice Drawing Structures
Formula
Lewis
Condensed
Line
C2H6
CH3CH3
C3H8
CH3CH2CH3
C5H12
CH3CH2CH2CH2CH3
or CH3(CH2)3CH3
C6H14
CH3CH2CH2CH2CH2CH3
or CH3(CH2)4CH3

6. Types of Organic Compounds
Classified according to functional groups
Alkane
Alcohol
Carboxylic acid
Alkene
Ether
Amine
Alkyne
Ketone
Amide
Haloalkane
Aldehyde
Amino acid

7. Big Idea in Organic Chemistry
Structure controls Function
Each functional group has predictable reactivity

8. Naming Alkanes (or Paraffins)
Made only of C and H
All C atoms are tetrahedral (only C-C single bonds)
General formula = CnH2n+2 (CH4, C2H6, C3H8, C4H10, etc.)
Alkanes are named based on the number of carbons in the longest chain! 8

9. Naming Basic Alkanes Alkane Alkyl substituents # of C atoms 1 2 3 4 56 7 8 9 10
CH4
CH3CH3
CH3CH2CH3
CH3CH2CH2CH3
Methane
Ethane
Propane
Butane
Pentane
Hexane
Heptane
Octane
Nonane
Decane
-CH3
-CH2CH3
-CH2CH2CH3
Methyl
Ethyl
Propyl
etc.
Root: number of C atoms
Suffix: functional group
(-ane for alkanes)
(-yl for alkyl groups)

10. Linear vs. Branched Alkanes
General formula = CnH2n+2 (CH4, C2H6, C3H8, C4H10)
Can have linear or branched alkanes
C5H12
Same molecular formula, different structure: structural isomers
Branches, including other atoms bonded, are called substituents. Common non-carbon ones are:
–NO2
–NH2 –F
–Br –I
nitro
amino
fluoro
bromo
iodo

11. Naming Branched Alkanes (IUPAC)
Octane
4-ethyl 6 2 8
4-ethyl-3,5-dimethyloctane 5 4 7 3 1
3-methyl and 5-methyl
= 3,5-dimethyl
Root name: name of longest continuous C chain (parent chain)
Two equally long? Choose the one with more branches
Number C atoms in chain, starting at end with first branch
Identify substituents, give each a number (C it is connected to)
Two or more identical substituents: use prefixes (di-, tri-, tetra-, etc.)
List substituents alphabetically before root name
Do not alphabetize prefixes
Punctuation: commas separate numbers from each other
hyphens separate numbers from names
no space between last substituent & root name

12. Provide each counterpart.1 2
5-ethyl-3-methyl
octane 3 5 7 4 6 8
(C11H24)
4-ethyl-2-methylhexane
(C9H20)

13. Naming Alkanes Practice
a. 2,4-dimethylpentane
b. 2,4-dimethylhexane
c. 2,4,6-trimethylheptane
d. 3-ethyl-2-methylpentane
e. 2,3-dimethylpentane
f. 2,2-dimethylhexane
g. 2,5-dimethylhexane
h. 4-methylheptane

14. Isomers
The fat dog shook himself, and then rolled over on the wet rug. OR
The dog shook the fat rug, then rolled over and wet on himself.
These two statements use the same words...
but have very different meanings!
Likewise, isomers may have the same formula, but have very different structures…

15. Structural Isomer Practice
On piece of your own paper, draw AND name ALL of the isomers for the following alkanes:
Formulas
# isomers
C5H12
C6H14
C7H16 3 5 9
Some of your drawings may look different, but they are only different structures (isomers) if they also have different names
If you complete that, try to draw and name all of the isomers for octane (C8H18) in your HW. There are 18 of them!

16. Structural Isomers: C5H12
pentane
2-methylbutane
2,2-dimethylpropane

17. Structural Isomers: C6H14
hexane
2,3-dimethylbutane
2-methylpentane
2,2-dimethylbutane
3-methylpentane

18. Structural Isomers: C7H16
heptane
2,2-dimethylpentane
2-methylhexane
2,3-dimethylpentane
3-methylhexane

19. Structural Isomers: C7H16
2,4-dimethylpentane
3-ethylpentane
3,3-dimethylpentane
2,2,3-trimethylbutane

20. Naming Practice
Two equal numbering options? Number based on alpha order 1 2 3 4 5 6 1 2 3 4 5 6
5-chloro-2-fluorohexane
2-chloro-5-fluorohexane
2-chloro-4-fluoro-2,3-dimethylpentane
2-bromo-3-ethyl-4-iodopentane
2-bromo-4-chloro-3-isopropylpentane

21. Provide each counterpart.Br
3-bromo-2-chlorohexane Cl I
2-ethyl-1,1-diiodo
heptane
2-methyl-1-nitrobutane
NO2
NH2
NO2
2-amino-6-nitro-3-propyl
heptane

22. Structural Isomers What are the possible structural isomers of C3H7Br?
1-bromopropane
2-bromopropane
What are the possible structural isomers of C4H9Cl?
1-chlorobutane
2-chloro-2-methylpropane
2-chlorobutane
1-chloro-2-methylpropane

23. Cycloalkanes Alkanes with closed ring(s) of C atoms
General formula: CnH2n (C3H6, C4H8, C5H10, etc.)
Naming: use cyclo- prefix before alkane name
cyclopropane
n = 3
cyclobutane
n = 4
cyclopentane
n = 5
cyclohexane
n = 6
C3H6
C4H8
C5H10
C6H12
Naming substituted cycloalkanes:
1 substituent: no numbering necessary
2 or more substituents: lowest numbering scheme, then by alpha
1-chloro-5-methylcyclohexane
methylcyclopentane
1-chloro-3-methylcyclohexane

24. Fun Common Names
broken
windowpane
boxane
windowpane
basketane

25. Teepane