Organic Chemistry

1. ETHERS

2. ETHERS
Ethers is an organic compound in which an oxygen
atom is bonded to two carbon atoms by single
bonds.

3. ETHERS
In an ether, the carbon atoms that are attached to
the oxygen atom can be part of alkyl, cycloalkyl,
or aryl groups.

4. Nomenclature
for Ethers

5. IUPAC Nomenclature for Ethers
Rule 1: Common names for ethers are formed by
naming the two hydrocarbon groups attached to
the oxygen atom and adding the word ether. The
hydrocarbon groups are listed in alphabetical order.
Ethyl methyl ether
Ethyl phenyl ether

6. IUPAC Nomenclature for Ethers
Rule 2: When both hydrocarbon groups are the
same, the prefix di- is placed before the name of the
hydrocarbon.
Dimethyl ether
Diethyl ether

7. IUPAC Nomenclature for Ethers
Alkoxy group
 an alkyl group attached to an oxygen atom.
 considered a substituent on the larger
hydrocarbon group.
Methoxy Ethoxy
Propoxy

8. IUPAC Nomenclature for Ethers
Naming an ether using the IUPAC system.
Rule 1: Select the longest carbon chain and use its
name as the base name.
CH3 – CH2 – O – CH2 – CH2 – CH3
Propane

9. IUPAC Nomenclature for Ethers
Rule 2: Change the -yl ending of the other
hydrocarbon group to -oxy to obtain the alkoxy
group name; methyl becomes methoxy, ethyl
becomes ethoxy, etc.
CH3 – CH2 – O – CH2 – CH2 – CH3
Propane
Ethoxy

10. IUPAC Nomenclature for Ethers
Rule 3: Place the alkoxy name, with a locator
number, in front of the base chain name.
CH3 – CH2 – O – CH2 – CH2 – CH3
Propane
Ethoxy
3
1 2
Answer: 1-Ethoxypropane

11. Learning Check
Assign IUPAC names to the following ethers.
Question # 1
CH3 – O – CH2 – CH2 – CH3
3
1 2
Answer:
1-Methoxypropane

12. Learning Check
Assign IUPAC names to the following ethers.
Question # 2
CH3 – CH – CH2 – O – CH2 – CH3
3 1
2
Answer:
1-Ethoxy-2-methylpropane
CH3

13. Learning Check
Assign IUPAC names to the following ethers.
Question # 3
CH3 – O – CH – CH2 – CH3
3
1
2
Answer:
2-Methoxybutane
CH3
4

14. Learning Check
Assign IUPAC names to the following cycloethers.
Question # 1
3
1
2
Answer:
Methoxycyclohexane
4
CH3 – O 4
5
6

15. Learning Check
Assign IUPAC names to the following cycloethers.
Question # 2
3
1
2
Answer:
1,3-Dimethoxycyclohexane
4
4
5
6
O – CH3
O – CH3

16. ETHERS
United States
 hydrocarbon ethane, CH2=CH2, is the organic
chemical produced in the largest quantities.
 methyl tert-butyl ether (MTBE), is the number
two organic chemical.

17. ETHERS
Methyl tert-butyl ether (MTBE)
 used as an octane
enhancer in gasoline.
 successor to tetraethyl lead
which was the major
gasoline additive before
the switch from leaded to
unleaded gasoline.

18. Functional
Group
Isomerism

19. Functional Group Isomerism
Functional group isomers are constitutional
isomers that contain different functional groups.
All three compounds have the molecular formula
C3H8O.

20. Functional Group Isomerism
Ethers and alcohols with the same number of
carbon atoms and the same degree of saturation
have the same molecular formula, (C2H6O).

21. Cyclic Ethers

22. Cyclic Ethers
Cyclic ethers contain ether functional groups as
part of a ring system. Some examples of such cyclic
ethers, along with their common names are follow: