If 3 UV active spots were in the crude material and co-spot TLC plate, and only one spot had the same Rf as the starting material and the other 2 are very different, predictions for the 2 non-starting material spots could be something in the middle of the mechanisms. There are four parts to the mechanism, the one in the middle are the ones that alter the mechanisms. So the second and third part of the mechanism would be the 2 non-starting material spots. This is because of the rate of the hydride attack on the carbon double bonded to the oxygen. It depends heavily on the R group present, and the more electron deficient it is, the faster the hydride can attack. But because they are different from the starting material spot, it would mean that it was caught between and could not fully reduced and go to completion. If it were to be the 1st and 4th instead of the two in the middle steps of this mechanism, it would go through but it will not be full.
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