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Organic Chemistry 2 Jasperse Test 1, Alcohol Chemistry Draw Mechanisms for the Following Reactions
1.
2.
3.
4.
5.
O OHMgBr1.
2. H+
MgBr1.
2. H+O OH
O
HMgBr
1.
2. H+
OH
MgBr1.
2. H+
OHO
H
MgBr1.
2. H+
OHO
T
T
T
RMgBr + Ketone1. Addition2. Protonation
RMgBr + Ketone1. Addition2. Protonation
RMgBr + Aldehyde1. Addition2. Protonation
RMgBr + Aldehyde1. Addition2. Protonation
RMgBr + Epoxide1. Addition2. Protonation
6.
7.
8.
9.
10.
1.
2. H+
OBrMg HO
O 1.
2. H+
OHLiAlH4
O OH
NaBH4, CH3OH
NaBH4, CH3OHO HO
MgBr1.
2. H+O
O (excess) OH
T
T
T
RMgBr + Epoxide1. Addition2. Protonation
RMgBr + Ester1. Addition2. Elimination3. Addition4. Protonation
Ketone + NaBH41. Addition2. Protonation
Ketone + NaBH41. Addition2. Protonation
Ketone + LiAlH41. Addition2. Protonation
11.
12.
13.
14.
MgBr1.
2. H+O
O (excess) OH
1.
2. H+
MgBr (excess)O
O
OHOH
1.
2. H+
OHO
OMgBr
OH
1.
2. H+O
O OHLiAlH4
T
T
T
RMgBr + Ester1. Addition2. Elimination3. Addition4. Protonation
RMgBr + Cyclic Ester1. Addition2. Elimination3. Addition4. Double Protonation
RMgBr + Cyclic Ester1. Addition2. Elimination3. Addition4. Double Protonation
LiAlH4 + Ester1. Addition2. Elimination3. Addition4. Protonation
15.
16.
17.
18.
19.
20.
1.
2. H+O CH3
O LiAlH4 OH
1.
2. H+
LiAlH4OO
HO
OH
1.
2. H+
LiAlH4
HOOH
O
O
OH BrHBr
HCl
OH Cl
OH Br
HBr
T
T
T
LiAlH4 + Ester1. Addition2. Elimination3. Addition4. Protonation LiAlH4 + Cyclic
Ester1. Addition2. Elimination3. Addition4. Double Protonation
LiAlH4 + Cyclic Ester1. Addition2. Elimination3. Addition4. Double Protonation
Tert Alcohol + HX to RX1. Protonate2. Loss of H2O3. Add halide
Tert Alcohol + HX to RX1. Protonate2. Loss of H2O3. Add halide
Tert Alcohol + HX to RX1. Protonate2. Loss of H2O3. Add halide
