An introduction to Organic chemistry.

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4. All organic compounds consist of carbon and hydrogen.
Many also contain oxygen and nitrogen
Other elements may also be present.
Phosphorous, halogens and/or metals
Most compounds are composed of carbon chains
bonded with hydrogen

5. H H H H H
| | | | |
H-C–C–C–C–C–H
| | | | |
H H H H H
A carbon / hydrogen chain (organic)
H H H H H
| | | | |
H-C–C–C–C–C–O-H
| | | | |
H H H H H
A carbon / hydrogen chain containing oxygen

6. Carbon can make four (4) bonds
Hydrogen can make one (1) bond
Oxygen can make two (2) bonds
Nitrogen can make three (3) bonds
Sulfur can make two (2) bonds
Halogens can make one (1) bond
|
– N–
–C–
|
|
- S–
H–
Cl -
-O-

7. Carbon can make single, double or triplebonds
Hydrogen can make only single bonds
Oxygen can make single or double bonds
|
–C–H
| –C=O
|
–C=O
| |
|
C–O-C
| |
C N

8. Nitrogen can make single, double or triplebonds
Sulfur can make single or double bonds
Halogens can make only single bonds
| |
H– N – H -C–S–C-
| | |
H
–C=S
–C=N |
| |
- C - Br
C N |

9. Naming Organic Compounds
Meth = 1 C
Eth = 2 C
Prop = 3 C
But = 4 C
Pent = 5 C
Hex = 6 C
Hept = 7 C
Oct = 8 C
Study this
Non = 9 C
Slide and
Dec = 10 C
then click here
To continue

10. Aliphatic Hydrocarbons
Alkanes – All single bond between carbons
(name ends in “ane”)
Alkenes – contains double bonds between carbons
(name ends in “ene”)
Alkynes – contains triple bonds between carbons
(name ends in “yne”)

11. Naming hydrocarbons starts with selecting the longest
Chain (even around corners).
H H H H H H
| Not 5 C| chain
| | | |
H-C–C–C–C – C–C-H
|
| | 7C |
| | H
c Name starts
H H H
h H H-C-H with “hept” (7C)
a
|
i All single bonds
n H- C–H Name ends with
| “ane”
H Heptane

12. Naming the Side Chain
H H H H H H
| | | | | |
H-C–C–C–C – C–C-H
|
| | | | | H Side Chain
H H H H H-C-H
|
H- C–H
|
H

13. Some Common Side Chains
H H H H
| | |
H- C- C -C - |
H -C -H
| | |
H H H |
Propyl Methyl
C3 H7 CH3
H
H H H H |
| | | | H -C -H
H- C- C -C -C - |
| | | | H- C -H
H H H H |
Butyl Ethyl
C4 H9 C2 H5

14. Methyl Heptane
H H H H H H
| | | | | | H
|
H-C–C–C–C – C–C-H H -C -H
|
| | | | | H |
H H H H H-C-H Methyl
|
H- C–H
| But where is the methyl
Group attached?
H

15. 3 methyl heptane
H H H H H H
Methyl group is
| | | | | | attached to the
H-C–C–C–C – C–C-H third carbon thus
| 3 methyl heptane
| | | | | H
H H H H H-C-H
|
H- C–H Count from the
Short end of
|
The chain
H

16. Two side chains
H
The first methyl
|
H -C -H group is on
H | H H H H the second
Carbon counting
| | | | | |
from the short
H-C–C–C–C – C–C-H end!
|
| | | | | H
The second methyl
H H H H H-C-H group is on
the fifth
|
Carbon counting
2, 5 dimethyl H- C–H from the short
heptane end!
|
H

17. Alkenes (Double bonds)
H H H H H H
| | | | | |
H-C–C–C–C = C–C-H
|
| | | | H
H H H H
A six Carbon chain – “hex”
2 hexene
Alkene – ends in “ene”
Double bond on second Carbon
From shortest end of chain

18. Alkene with two side groups
H
|
H -C -H
H | H H H H
| | | | | |
H-C =C–C–C – C–C-H
|
| | | H
H H H-C-H
|
2, 5 dimethyl H- C–H
1 heptene
|
H

19. Alkynes (triple bond)
Longest chain
8 Carbons
H H H H H H (oct)
| | | | | |
Triple bond
H-C–C–C–C – C–C–C C-H on C atom 1
| (“yne”)
| | | | |
H
H H H H H-C-H
| 2 Carbon
Side chain
4 ethyl 1 octyne H- C–H (ethyl) on
| C atom 4
H

20. General Formula
Propane
Alkanes (Single bonds) Cn H(2n +2) C3 H8
Propene
Alkenes (Double bonds) Cn H2n C3 H6
Propyne
Alkynes (triple bonds) Cn H(2n -2) C3 H4

21. |
Common
O -H Organic
Hydroxyl
Groups
– N–H
|
H
Amine
–C=O
|
O
|
Ester Linkage

22. –C=O | |
|
-C–O–C-
O -H | |
Carboxyl Ether Linkage
–C=O
–C=O N–H
C
|
| |
H
Carbonyl Amide

23. Some functional groups are combinations of smaller
functional groups
| | –C=O
–C=O
| + -C–O–C- = O
|
| | |
Carbonyl Ether Linkage Ester Linkage

24. | –C=O –C=O
O -H + | = |
Hydroxyl Carbonyl O -H
Carboxyl
–C=O
C – N–H
– N–H
+ –C=O =
|
| |
| H
H
Amine Carbonyl Amide

25. Compounds Containing Functional Groups
Alcohols
-O-H H
Ethyl |
End in “ol”
C2 H5 H -C -H
|
H- C -H
|
O-H
Ethyl Alcohol
Ethanol
R –OH
R = a Carbon/ Hydrogen chain
Common name
Grain alcohol

26. Compounds Containing Functional Groups
H
|
ketones H -C -H
–C=O |
C=O
| |
H -C -H
End in “one” |
H- C -H
|
H
R– C = O
Methyl ethyl ketone
|
R Butanone
R = a Carbon/ Hydrogen chain 2 butanone is incorrect
Since counting from either
end would put the carbonyl
On the second Carbon

27. Compounds Containing Functional Groups
Aldehydes
H
–C=O |
| H -C -H
H |
End in “al” H - C=O
R – C=O
Ethyl Aldehyde
|
H Ethanal
R = a Carbon/ Hydrogen chain
Common name
Acetaldehyde

28. Compounds Containing Functional Groups
Acids
–C=O H
| |
H -C -H
O -H |
End in “oic” C=O
|
R– C = O O -H
| Acetic Acid
O -H
Ethanoic Acid
R = a Carbon/ Hydrogen chain
Common name
Vinegar

29. Structural Isomers
Same formula but different arrangement of atoms
H H H H H H H
| | | | | | |
H- C- C -C -C -H H- C- C -C -H
| | | | | | |
H H H H H | H
H–C–H
Butane |
C4 H10 H
Methyl Propane
C4 H10

30. Propanone Propanal

32. Chiral Carbons
Mirror Image molecules

33. Molecules Cannot be Superimposed!
Out of screen Into screen

35. Cis and Trans Isomers
Double bond
cis-butenedioic acid trans-butenedioic acid
(maleic acid) (fumaric acid)
“cis” like scissors (next to) “trans” across form

36. Aromatics
Aromatics are compounds that contain a
benzene ring as part of their structure
C6 H6

37. Delocalized
Electron
cloud
Resonance structure

38. Different symbols for the Benzene Ring

39. Some Common Aromatics
Aspirin

40. Cyclics and Aromatics
C6 H6
At first glance they look the same but aren’t