Download + Dess- MgBr Martin

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Transcript 
Make the following molecules beginning with alcohols having five or fewer carbons.
DessOH Martin
MgBr
+
O
2) H O+
POCl
OH
3
3
Mg, ether
OH
PBr
Br
3
PBr
OH
Could also be synthesized by
reversing Wittig reagent and
carbonyl compound. (ie.
4-methylbutanal)
Br
3
1) PPh
PPh 3
3
2) n-BuLi
Jone's
Reagent
OH
Jone's
reagent
+
OH
O
3
+
BrMg
Mg
ether
PBr
HO
O
OH
2) H O+
3
Br
2) H O+
3
OH
Jone's
reagent
O
+
OH
O
H+
HO
+
O
BrMg
Grignard reagent
made previously
(above left)
OH
Jone's
reagent
O
(CrO , H SO )
3
2
OH
+
BrMg
2) H O+
3
4
Mg
ether
PBr
HO
3
Br
POCl
3
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