Propose a mechanism for the following Birch or metal dissolving reduction reaction (Note: knowledge o intermete (ree radical) stability is critical): 1 1. Na, NH3 (liq.) 2. NH4CI
2. Show a complete mechanism for the Birch reduction of toluene.
3. A) What is the major product of the following Birch reduction. B) Will the rate of the reaction be faster, slower, or the same if the starting material was benzene? Na(s), CH3OH NH3
ma Predict the product from the Birch reduction shown below: (3 pts) | Na, NH, CH OH
HIO4 OsO4 t-BOOH t-BuOH, өОН K2Cr207 H2504, H20 "нн HCI heat O = 0 Na SME Me OH TsOH = Me TSOH
10. Show the mechanism for the reduction of benzene to 1,4-cyclohexadiene under Birch conditions. Why can’t an alkyl benzene get reduced? (4pts)
Mechanism for this reaction
Na NH3 liquid, -78°C
Provide a complete mechanism for the following reaction. 1 t-BuOH (1 eqv) 2. CH3CH2Br
9.44 Propose a mechanism for each of the following transformations: Na NH3 )
9.44 Propose a mechanism for each of the following transformations: Na NH3 )