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Ether
Oxygen partially negative
Carbons partially positive
More Soluble in water than hydrocarbons
Lower bp than alcohols
Oxirane
high strain on carbons
undergoes many ring-opening reactions with nucleophiles
Oxetane
Oxolane
oxane
Crown Ether
18-Crown-6
Alkoxide
Epoxide
Simple epoxides named based off oxirane
More complex = epoxy
Peroxycaroxylic acid
used in epoxide synthesis
Glycol
Epichlorohydrin
each 3 carbons have a reactive functional group
Thioether
S rather than O
Alcohol
sp
3
hybridized
1
0
2
0
3
0
Lewis Acid
Can accept electrons
Lewis Base
Donates a pair of electrons
Electrophile
"electron-lover"
accepts electrons (lewis acid)
usually positivelt charged
Nucleophile
"nucleus-lover"
donates a pair of electrons (Lewis base)
Willaimson Ether Synthesis
best when leaving group is primary or methyl
Sn
2
Typically O
+
Na
-
with Br
+
or I
+
leaving group
Alkoxide is the nucleophile
2(CH
3
)-C=CH
2
+ CH
3
OH --> 3(CH
3)
-C-O-CH
36y
Acid-Catalyzed Addiction of Alcohols
Alkenes that form stable carbocations
Methanol or primary alcohols
1.
Acid protonates carbon
2.
Electrophilic carbocation reacts with nucleophilic alcohol to make oxonium
3.
Proton transfer to solvent to stabalize
CH
3
(3CH
2
)-O-(3CH
2
)CH
3
+ 2 HBR --heat--> 2 CH
3
(3CH
2
)Br + H2O
Acid-Catalyzed Cleavage of Concentrated HX
Requires strong acid and good nucleophile (HI or HBR)
If both carbons are primary... Sn
2
Otherwise... Sn
1
Tertiary, allylic or Benzylic ethers are particularly susceptible
Epoxidation of an Elkene by Peracid Oxidation
Nonpolar solvents
stereospecific!
Epoxide and carboxylic acid product
Insert picture from phone
Internal Substitution of Halohydrin
1.
Treat alkene with Br
2
or C
l2
in water
2.
treat halohydrin with a base (NaOH) to displace Cl or Br
Stereoselective
Internal Sn
2
Inversion of configuration
2 ways to create epoxides
Perocycarboxylic Acids and Substitutions in Halohydrins
General Characteristics of Epoxide Reactions
Epoxide + H-Nu
: ----> OH
(up)
-C-C-Nu
(down)
Stereoselective
Author
JessieP
ID
10964
Card Set
Organic Chemistry
Description
Alcohols and Ethers
Updated
2010-03-22T18:42:02Z
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