Ether Synthesis
1. Williamson Ether Synthesis
(SN2)
2. Mineral Acid, Ether Synthesis
(SN2 or SN1)
Williamson Ether Synthesis
+
Methyl or
1o Elec.
(Unbranched)
SN2
Ether
Diethyl Ether
“Has an Ethyl on Ether side of the O.”
“Successful Williamson
Ether Synthesis”
“Make Alkoxide
if not given”
Na
“1o Elec.,
SN2 is Major”
Alkoxide
SN2
(Click “Slideshow” to Animate)
Ether Synthesis
1. Williamson Ether Synthesis
(SN2)
Williamson Ether Synthesis-Failed Attempt!
+
Methyl or
1o Elec.
SN2
Ether
“Unsuccessful Williamson
Ether Synthesis”
“2o Elec.,
E2 is Major”
Alkoxide
E2
“Strong Base”
“2o Elec., too much Steric Hind. for SN2 w/ a Strong Base”
Willie’s having a Bad Trip Man…
We’ll have to talk him down.
Ether Synthesis:
2. Mineral Acid, Ether Synthesis
(SN1 or SN2)
Alcohol
Ether
Alcohol
Mineral Acid
H2SO4
“H2SO4 is a Mineral Acid.”
“Alcohol,
BAD L.G., BAD!”
“Gooood L.G.!”
“Weak
Nuc.”
“3o Carbocation, Ultra Strong
Elec.”
SN1
Ether Synthesis
2. Mineral Acid, Ether Synthesis
(SN1 or SN2)
Alcohol
Ether
Alcohol
Mineral Acid
H2SO4
“Alcohol,
BAD L.G., BAD!”
“Gooood L.G.!”
“1o Elec., no SN1
but SN2 will work enough.”
SN2
“Alcohols are weak Nuc’s but will still work under these Acidic Conditions.”
Actual Quiz on the following Slides
(Key above)
Use colors for reacting electrons.