1. The oxidation of benzyl alcohol with the (bpy)CuTEMPO system studied can be c
ID: 584230 • Letter: 1
Question
1. The oxidation of benzyl alcohol with the (bpy)CuTEMPO system studied can be complete in three hours, while oxidation of octanol requires upwards of 20 hours to achieve comparable yield. Suggest an explanation for the slower reactivity of octanol 2. 4-hydroxy benzyl alcohol is not capable of undergoing oxidation with the present (bpy)CuTEMPO catalytic system, where the starting material is largely recovered at the end of the reaction, as evidenced by GC. Propose an explanation as to why no reaction is observed. 3. When a co-solvent of 1:1 H20:CH,CN is employed the oxidation of a primary alcohol with the (bpy)Cu/TEMPO system is much slower than with acetonitrile as a solvent. How can you account for this observation? 4. You are asked to carry out the following transformation. Propose a recently published approach (ie. 2012- 2014), and explain why you would choose this approach over the current (bpy)Cu'lTEMPO system. Be sure to cite your references. 5. Provide a mechanism for the transformation of 7 to a quinoline with addition of 2-butanone and NaOH. NH2Explanation / Answer
1)
The mechanism with tempo goes through radical formation.
So when benzyl alcohol is considered, benzyl radical is more stable when compared to primary radical. Hence benzyl alcohol oxidises faster than octagon.
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