1. Naming Hydrocarbons

2. copyright 2002 by Amelia Potter
Hydrocarbons
Alkanes
Alkenes
Alkynes
CnH2n+2
CnH2n
CnH2n-2
All C bonds are single (fully saturated)
C=C (double bond)
unsaturated
Triple C bond
CH3CH3
ethane
CH2CH2
ethene
CHCH
ethyne
copyright 2002 by Amelia Potter

3. How can we represent Alkanes?
C – C – C – C – C Demonstration (No H)
H H H H H
| | | | |
H - C – C - C – C - C – H Fully Expanded
H H H H H
CH3 – CH2 – CH2 – CH2 – CH Condensed
CH3 CH2CH2CH2CH Fully Condensed
C5H Molecular Formula
copyright 2002 by Amelia Potter

4. Naming Alkanes (all single bonds)
Chain Length
In Carbons
Name
Alkane name
Alkane Formula CnH(2n+2) 1
meth
methane
CH4 2
eth
ethane
C2H6 3
prop
propane
C3H8 4
but
butane
C4H10 5
pent
pentane
C5H12 6
hex
hexane
C6H14
copyright 2002 by Amelia Potter

5. Rules for Naming of Alkanes
Determine the longest continuous carbon chain: also known as the PARENT CHAIN!!!!
copyright 2002 by Amelia Potter

6. copyright 2002 by Amelia Potter
Example
Count from one end to another, and determine the longest carbon chain (parent chain)
C –C-C-C– C
| hexane
C – C
Use longest chain in any direction
copyright 2002 by Amelia Potter

7. copyright 2002 by Amelia Potter
Chain Length
C –C-C-C-C-C-C
| nonane
C-C-C-C-C-C
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Naming the Chain
C –C –C -C –C –C -C – C
| decane
C – C – C – C – C –C -C – C
copyright 2002 by Amelia Potter

9. copyright 2002 by Amelia Potter
Naming Alkanes
Determine Chain Length
Use longest Chain (parent chain)
Name the longest chain
Use ending for alkane (“ane”)
copyright 2002 by Amelia Potter

10. Naming Branches (Side Chains)
After naming the longest chain, draw a line through all the carbons you use.
Everything that is left are the side chains.
Name the side chain (branch) using the “yl” ending (methyl, ethyl, propyl, etc)
copyright 2002 by Amelia Potter

11. copyright 2002 by Amelia Potter
Naming Side Chains
Side Chain Length
In Carbons
Name
Side chain name
Alkyl Formula 1
meth
methyl
- CH3 2
eth
ethyl
- C2H5 3
prop
Propyl*
- C3H7 4
but
Butyl*
- C4H9 5
pent
pentyl
- C5H11 6
hex
hexyl
- C6H13
* isopropyl, n-butyl, s-butyl,t-butyl
copyright 2002 by Amelia Potter

12. copyright 2002 by Amelia Potter
Naming the Side Chain
Determine the longest chain (parent chain) – name it!
Number the carbon atoms in the parent chain starting from the end that is CLOSEST to a branch/side chain
Name the side chain and indicate on which carbon it’s located
C –C-C-C– C |
C – C
Parent Chain: hexane
copyright 2002 by Amelia Potter

13. Naming - Side Chain Locator Number
Numbering right to left : ←
C –C-C-C- C |
C – C ←
the side chain is on the #3 carbon of hexane
C –C-C-C- C |
C – C
copyright 2002 by Amelia Potter

14. copyright 2002 by Amelia Potter
Numbering left to right: →
C –C-C-C- C |
C – C →
the side chain is on the #4 carbon of hexane
C – C-C-C- C |
C – C
copyright 2002 by Amelia Potter

15. Naming – Side Chain Locator Number
3 is lower than 4, so use 3 3
C –C-C-C- C |
C – C
3 – methylhexane
copyright 2002 by Amelia Potter

16. copyright 2002 by Amelia Potter
Naming the Side Chain
C –C-C-C – C -C-C |
C –C-C-C-C -C-C
5- ethyl-6- ethyl decane
OR:
5,6-diethyl decane
copyright 2002 by Amelia Potter

17. copyright 2002 by Amelia Potter
Multiple Side Chains
C –C –C -C –C -C-C-C |
C – C – C – C – C-C-C
Parent: decane
6-ethyl-5- propyldecane
ALWAYS list side chains alphabetically – E for Ethyl before P for Propyl
copyright 2002 by Amelia Potter

18. copyright 2002 by Amelia Potter
C – C – C |
C – C – C – C – C - C – C – C
Parent Chain: octane
Side Chain: isopropyl (not just propyl)
Name: 4-isopropyloctane
copyright 2002 by Amelia Potter

19. Halogen Substituted Carbon Hydrogen
(one hydrogen substituted by a halogen (X))
Name by the Halogen used in the compound
Chloroalkanes (C-C-Cl)
Bromoalkanes (C-C-Br)
Flouroalkanes (C-C-F)
copyright 2002 by Amelia Potter

20. copyright 2002 by Amelia Potter
Naming the Chain
C –C-C-C– Cl |
C – C
Parent Chain: hexane
Side chain: 3-chloro
Name: 3 - chlorohexane
copyright 2002 by Amelia Potter

21. copyright 2002 by Amelia Potter
Naming the Chain
C –C -C –C -Cl |
C – C – C – C – C –C-C-C – C
decane
chloro propyl decane
4 - chloro 5-propyl decane
C –C -C –C -Cl |
C – C – C – C – C –C-C-C – C
copyright 2002 by Amelia Potter

22. copyright 2002 by Amelia Potter
Naming the Chain
C –C -C - Cl |
C – C – C – C – C – C - C –C -C – C
Let’s name this:
copyright 2002 by Amelia Potter

23. copyright 2002 by Amelia Potter
Naming the Chain
Example 13
C –C –C -C - Br |
C – C – C – C – C - C –C -C – C
nonane
bromo butyl nonane
4 - bromo 5 - butyl nonane
C –C –C -C - Br |
C – C – C – C – C - C –C -C – C
copyright 2002 by Amelia Potter

24. copyright 2002 by Amelia Potter
DONE with Alkanes!
Your turn to practice!
copyright 2002 by Amelia Potter

25. copyright 2002 by Amelia Potter
Naming Alkenes
Determine the longest continuous chain of carbons that have the double bond between two of its carbons. The parent chain must contain the double bond.
C – C – C = C – C – C –C
copyright 2002 by Amelia Potter

26. copyright 2002 by Amelia Potter
Naming Alkenes
Number the carbons in the chain so that the double bond would be between the carbons with the lowest designated number.
C1 – C2 – C3 = C4 – C5 – C6 –C7
3-heptene
copyright 2002 by Amelia Potter

27. copyright 2002 by Amelia Potter
Naming Alkenes
The location of the double bond, not the location of the branches are used for numbering the alkene.
NOTE THE –ENE ending as well!
copyright 2002 by Amelia Potter

28. copyright 2002 by Amelia Potter
Naming Alkenes
Identify the side chains/branch and the position of the branch.
The format is as follows:
(location of branch)-(branch name)(parent chain)
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Cis and Trans Isomers
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Example
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Example:
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32. copyright 2002 by Amelia Potter
Naming of Alkynes
Indentify the parent chain with the TRIPLE bond!
Number from the end closest to the TRIPLE bond!
Ending is –YNE
Ethyne, propyne, 1-butyne, etc…
All other rules of naming are the same as for the other hydrocarbons
copyright 2002 by Amelia Potter

33. Cycloalkanes Carbon atoms that are joined in a ring or circle
Simplest: cyclopropane
Another: cyclohexane

34. Naming Add cyclo- Otherwise fairly similar to regular naming
Draw structures for the following compounds
Cyclooctane
Ethylcyclohexane
1,1,2-trimethylcyclobutane

35. Answers A. B. C.

36. Draw these structures Cyclopentane 1-ethyl-2-methylcyclopentane
1-ethyl-1,2,5,5-tetramethylcycloheptane

37. Answers A. B. C.

38. Alkenes End in -ene Unsaturated hydrocarbons
Have a double bond (CH3=CH2)

39. Aromatic Compounds Benzene Named because thought to have strong aroma
Now define as anything that has a benzene ring
Aliphatic compounds—nonaromatic

40. Naming
One substituent…easy