1) They often detonate without warning when ether solutions are distilled to near
dryness ⇒ test for and decompose any ether peroxides before a distillation is
carried out.
- Diethyl ether was first used as a surgical anesthetic by C. W. Long of Jefferson,
Georgia, in 1842 and shortly after by J. C. Waren of the Massachusetts General
Hospital in Boston.
- The most popular modern anesthetic is halothane (CF 3 CHBrCl). Halothane is
not flammable.
11.4 SYNTHESIS OF ALCOHOLS FROM ALKENES
- Acid-Catalyzed Hydration of Alkenes:
- Water adds to alkenes in the presence of an acid catalyst following
Markovnikov’s rule.
i) The reaction is reversible.
CCHA C
H
C
+H 2 O
−H 2 O
O
HH
O H
CC H
H
CC
H
+ + + A
Alkene Alcohol
+ A− +A−
+
2) Because rearrangements often occur, the acid-catalyzed hydration of alkenes
has limited usefulness as a laboratory method.
- Oxymercuration-Demercuration:
- Oxymercuration-demercuration gives Markovnikov addition of H– and –OH to
an alkene, yet it is not complicated by rearrangement.
- Hydroboration-Oxidation:
- Hydroboration-oxidation gives anti-Markovnikov but syn addition of H–
and –OH to an alkene.
