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CHAPTER 10
Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Important Terms
alcohol
an alkane with an OH group in place of an H (ROH).
alkaloid
amines found in the leaves, bark, roots, or seeds of plants.
alkyl tosylate
an ester of
para-
toluenesulfonic acid.
crown ether
a cyclic molecule that possesses several ether linkages around a central cavity.
dehydration
loss of water.
epoxide
an ether in which the oxygen is incorporated into a three-membered ring.
ether
a compound containing an oxygen bonded to two carbons (ROR).
inclusion compound
the complex formed when a crown ether specifically binds a metal ion or an
organic molecule.
Hofmann elimination
elimination of a proton and a tertiary amine from a quaternary ammonium hydroxide.
reaction
lead compound
a prototype in a search for other physiologically active compounds.
mercapto group
an SH group.
molecular modification
changing the structure of a lead compound.
quaternary ammonium ion
a cation containing a nitrogen bonded to four alkyl groups
1
R
4
N
+
2
.
sulfide (thioether)
the sulfur analogue of an ether
1
RSR
2
.
sulfonate ester
the ester of a sulfonic acid
1
RSO
2
OR
2
.
sulfonium salt
R
3
S
+
X
-
thioether (sulfide)
the sulfur analogue of an ether
1
RSR
2
.
thiol (mercaptan)
the sulfur analogue of an alcohol
1
RSH
2
.