Illustrated Glossary of Organic Chemistry
Sodium
hydride
(Na
H
):
The sodium
salt
of the
conjugate base
of H
2
; Na
+
:H
-
. A strong
base
(H
2
p
K
a
35). Despite its high
basicity
, Na
H
is not
nucleophilic
.
Na
H
THF
+ H
2
Use of Na
H
to generate an
alkyne anion
by
deprotonation
of the
terminal
hydrogen of
propyne
.
Related terms:
Hydride
,
sodium borohydride
,
NaBH
4
,
lithium diisopropyl amide
,
LDA
,
butyllithium
,
BuLi
,
sodium amide
,
NaNH
2
,
sodamide
,
THF
,
tetrahydrofuran
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