Kayden Evans

1
ETHER

• Kayden Evans
• Taylor Segell
• Gabriela Torres
• 5p

2
Basic Structure
Ethers always have to have an oxygen in the
center. They can have hydrogen and carbon bound
off of each side but the oxygen must remain in
the middle.
3
CHARACTERISTICS

• Ether molecules cannot form hydrogen bonds with
  each other, making their boiling points low.
• The C-O-C bond angle in the functional group is
  about 110.
• Ethers are slightly polar, more polar than
  alkenes but not as polar as alcohols, esters, or
  amides.

4
CHARACTERISTICS

• Because of the nature of the positive charge on
  the ether hydrogen atoms, the hydrogens cannot
  participate in hydrogen bonding. So, ethers only
  form hydrogen bonds to other molecules that have
  hydrogen atoms with strong partial positive
  charges.

5
NOMENCLATURE

• "Simple" ethers
• If both groups are simple alkyl groups, then the
  ether is usually named as alkyl alkyl ether
• If the two alkyl groups are the same, then it's a
  dialkyl ether
• Ex. CH3 CH2 O CH3
• Functional group is a simple ether, therefore
  use alkyl alkyl ether
• First substituent is C1 alkane therefore alkyl
  methyl
• Second substituent is C2 alkane therefore alkyl
  ethyl
• CH3 CH2 O CH3 ethyl methyl
  ether
• Ex. CH3 CH2 O CH2 CH3
• Functional group is a simple ether, therefore use
  alkyl alkyl ether
• Both substituents are C2 alkane therefore alkyl
  ethyl
• Since there are two alkyl groups, multipler di
• CH3 CH2 O CH2 CH3 diethyl
  ether

6
NOMENCLATURE

• Ex. CH3 O CH3
• Functional group is a simple ether, therefore use
  alkyl alkyl ether
• Both substituents are C1 alkane therefore alkyl
  methyl
• Since there are two alkyl groups, multipler di
• CH3 O CH3 dimethyl ether

7
MECHANISMS

• Sulfuric acid dissociates
• The alcohol's oxygen atom is protonated with an
  acid-base reaction, forming an oxonium ion
• 3. The oxonium ion decomposes
• 4. The oxonium ion liberates a proton to create
  the ether

Ethers can be synthesized in standard SN2
conditions by coupling an alkoxide with a
haloalkane or sulfonate ester. The alcohol that
supplies the electron rich alkoxide is used as
the solvent, as well as dimethyl sulfoxide (DMSO)
8
MECHANISMS
Ethers are stable, non-reactive compounds. The
linkage is stable towards bases, oxidizing
agents, and reducing agents. Ethers undergo just
one kind of basic chemical reaction cleavage by
acids. Cleavage takes place under
vigorous conditions concentrated acids and high
temperatures.
or the reaction can occur by way of an SN2
mechanism. The reaction mechanism
depends upon the reaction conditions and the
structure of the ether. A primary alkyl group
tends to undergo SN2 displacement
9
EXAMPLES
In alcohols, one of the two bonds to the oxygen
atom involves hydrogen and one involves carbon.
Such compounds are called ethers. For example,
dimethyl ether is isomeric with ethanol, and
methyl ethyl ether is isomeric with propanol.
Crown Ethers These cyclic polyethers can form
chemical complexes with metal cations (such as
lithium, sodium, and potassium cations), thus
holding the cations in solution. The size of the
interior of the crown ether determines the size
of the cation it can solvate
10
EXAMPLES
What differentiates a halogenated ether from
other types of ethers is the substitution of one
or more hydrogen atoms with a halogen atom.
Halogen atoms include fluorine, chlorine,
bromine, and iodine. Halogenated ethers have the
advantages of being non-flammable as well as less
toxic than earlier general anesthetics.
Isoflurane halogenated ether
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REAL WORLD IMPORTANCE

• Diethyl Ether
• Uses highly flammable liquid, solvent and an
  anesthetic.
• Fuel used as the starting fluid for diesel and
  gasoline based engines.
• Solvent Many scientist have been known to use
  ether as a solvent because of its limited
  solubility in water. This makes sets it up to
  preform liquid to liquid extractions.
• Anesthetic Ether has been used worldwide by
  doctors when preforming anesthesia on patients.

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A World without ether?

• Ether has proven to be a very useful and
  important in the progress of man.
• Without Ether the vast majority of petroleum
  based engines would have no kick start.
• Also without Ether anesthetic use in the late
  1800s, modern day anesthetics may be drastically
  different.

13
Questions

• What is typical structure of an ether?
• If both groups are simple alkyl groups, then the
  ether is usually named as _____ _____ _____?
• If the two alkyl groups are the same, then it's a
  ______ _____?
• What is the one basic chemical reaction ethers
  undergo?
• Cleavage only occurs under what two conditions?

14
Answers

• Ethers always have to have an oxygen in the
  center. They can have hydrogen and carbon bound
  off of each side but the oxygen must remain in
  the middle at an angle of 110 degrees.
• Alkyl Alkyl Ether
• Dialkyl Ether
• Clevage
• Concentrated Acids and High Temperatures.

15

• http//www.chem.ucalgary.ca/courses/351/orgnom/eth
  ers/ethers-01.html

• http//www.cliffsnotes.com/study_guide/Ethers.topi
  cArticleId-23297,articleId-23273.html

• Work Cited

• http//www.newworldencyclopedia.org/entry/Ether

• http//chemed.chem.wisc.edu/chempaths/GenChem-Text
  book/Ethers-922.html