Download Chapter 17 - Ellis Benjamin

Chapter 17
Know what pKa means?
QUESTION: If I have a high pKa will I dissociates easily?
Know what electron inductive effects do (below)
QUESTION: Place in order of the pKa from high to low.
O H
O H
H3C
O H
CH3
O2N
CH3
NO2
NO2
Hydromecuration –Synthesis of Alcohols from an Alkene (Markinov)
H
H
H
HO
1) Hg(OAc)2, H2O, THF
2) NaBH4
H
H
CH 3
CH 3
Hydroboration – Synthesis of Alcohols from an Alkene (Anti-Markinov)
H
H
H
H
H
1) BH3, THF
2) -OH, H2O2
H
H
OH
H
H
1,2 Diol Synthesis with Osium tetraoxide (Syn Addition)
CH 3
CH 3
OH
O O
Os
O O
+
pyridine
OH
or OsO 4
Reduction of and Ketone or Aldehyde using Sodium Borohydride to form and
Alcohol.
O
OH
1) NaBH4, ethanol
2)H3O+
Reduction of and Ketone or Aldehyde using Lithium Aluminum Hydride to form
and Alcohol.
O
OH
1) LiAlH4, ether
2)H3O+
GRINGARD SYNTHESIS (KNOW THIS)
OH
Br
MgBr
Mg
O
+
O
Mg
Br
MgBr
QUESTION: Do this reaction
MgBr
O
+
Dehydration
Base Catalyzed
OH
KOH
+
OH
Acid Catalyzed
OH
H3O+
Phosphorus oxychloroide
OH
POCl 3
Oxidation of Alcohols With PCC