Download Sources of hydride ion

Survey
yes no Was this document useful for you?
   Thank you for your participation!

* Your assessment is very important for improving the work of artificial intelligence, which forms the content of this project

Document related concepts

Peptide synthesis wikipedia, lookup

Marcus theory wikipedia, lookup

Haloalkane wikipedia, lookup

Alkene wikipedia, lookup

Stille reaction wikipedia, lookup

Hydroformylation wikipedia, lookup

Strychnine total synthesis wikipedia, lookup

Alcohol wikipedia, lookup

Discodermolide wikipedia, lookup

Wolff–Kishner reduction wikipedia, lookup

Ene reaction wikipedia, lookup

Petasis reaction wikipedia, lookup

Asymmetric induction wikipedia, lookup

Elias James Corey wikipedia, lookup

Cracking (chemistry) wikipedia, lookup

Ring-closing metathesis wikipedia, lookup

Nucleophilic acyl substitution wikipedia, lookup

Enantioselective synthesis wikipedia, lookup

Wolff rearrangement wikipedia, lookup

Diels–Alder reaction wikipedia, lookup

Transcript
Sources of hydride ion
H
Na+
H
H
B
H
B
H
H
NaBH4
less
reactive
LiAlH4
very
reactive
H
H
Li+
H
H
Al
H
Al
H
H
H
H
Al
D
DIBALH
specially
i ll used
d ffor
ester  aldehyde
diisob t lal min m hydride
diisobutylaluminum
h dride
1
Reduction reactions with
h NaBH4
2
Reduction reactions with
h NaBH4
esters
carboxylic acids
NaBH4
reduction products DO NOT form
amides
3
Reduction of esters with
h LiAlH4
-- LiAlH4 is more reactive th
han NaBH4
4
Reduction of carboxylic acids with LiAlH4
5
Reduction of amides witth
th LiAlH4
6
7
Reduction of esters with
h DIBALH
-- DIBALH is less reactive than LiAlH4
8
Sodium borrohydride
9
Lithium alum
minum hydride
10
DIBALH (i-Bu2AlH)
11
Stereochem
mistry
12
Definition of Re fa
ace and Si face
1
O
Re
C
Si
CH2CH3
H3C
2
3
13
Stereochem
mistry
14
Stereochem
mistry
15
Reactions for ketone/alldehyde
ldehyde – type II:
16
Reactions wiith water
Water adds to an aldehyde or kettone to form a hydrate:
H+
17
Mechanism for acid-cata
alyzed
y
hydrate
y
formation
18
19
20
Reactions wiith
ith alcohols
21
Mechanism for acid-catalyzed ace
etal or ketal formation:
etal
22
Formation of cyclic
y c ketals and acetals
-- act as protecting
g groups
23
Why
yp
protecting
gg
gro
oups?
p
Utilization of protecting groups
g
in synthesis:
24
Protecting
gg
groups
p
25
Protecting
gg
groups
p
26
Reactions wiith
ith thiols
Hg2+
Hg2+
27
Desulfurization replace
p es the C-S bonds
with C-H bonds
28
Reactions of ketones/alde
ehydes with primary amines
ehydes
29
Reactions of ketones/alde
ehydes with 2o amines
ehydes
30