1. Two of the proposed mechanisms (one Oxone mechanism and one permanganate mech
ID: 934226 • Letter: 1
Question
1. Two of the proposed mechanisms (one Oxone mechanism and one permanganate
mechanism) be eliminated immediately. Discuss which ones, being
specific about what makes them unreasonable.
2. There are several ways to measure the
1. Two of the proposed mechanisms (one Oxone mechanism and one permanganate mechanism) be eliminated immediately. Discuss which ones, being specific about what makes them unreasonable. 2. There are several ways to measure the greenness of a chemical process. The atom economy of a reaction is one such metric, and one of the more popular methods for comparing the efficiencies of different reactions. In an ideal chemical process, each atom in the reactants is incorporated into the products, producing no waste16. Based on this metric, discuss which reaction is more efficient.Explanation / Answer
1.
Permanganate reaction mechanism:
Mechanism B is correct.
Mechanisms A and C involve removal of an oxide ion O2- from MnO4- which is practically very difficult. Hence, these two mechanisms must be eliminated.
Oxone mechanism:
mechanism A is correct.
mechanism B is incorrect because that's a very long route to synthesize the diol. Also, the aldehyde bi-product can react with the diol to give an acetal. This mechanism must be eliminated.
mechanism c is also incorrect. The electron flow is incorrect. C=C from cyclohexene can give a pair of electrons to only one oxygen and not both. Hence, this mechanism should also be eliminated.
2.
In permanganate reaction mechanism:
C6H10 + MnO4- + H2O ----> C6H10(OH)2 + MnO2
In this reaction, one oxygen from reactant is left out and not incorporated in the product.
In oxone reaction mechanism:
C6H10 + (CH3)2CO2 + H2O ----> C6H10(OH)2 + (CH3)2CO
In this reaction, all reactants are incorporated into the product.
Hence, according to 'atom economy' metric, oxone reaction is more efficient.
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