b) When 4-t-butyl-1-methylpiperidine was oxidized by H202. N-oxides P and Q were

Question

b) When 4-t-butyl-1-methylpiperidine was oxidized by H202. N-oxides P and Q were formed irreversibly in a ratio of 10:90 H202 Me kinversion 108 s-1 kp 90% 10% i) (3 pts) In light of the protonation study in a) and based on these new findings, how would the rates for oxidation (kp, ko) compare to the rate of nitrogen inversion (kinversion)? A) Oxidation is faster than nitrogen inversion B) Oxidation is slower than nitrogen inversion C) It is impossible to know from this information. i) (3 pts) Briefly explain your answer.

Explanation / Answer

i) B. Oxidation is slower than nitrogen inversion.

ii) If the oxidation was faster then the N would not have got the time for inversion, so that P would have been the major product as it directly undergoes oxidation . However, since the inversion is faster, kinetically more favoured intermediate (B) is formed faster and thus the product q is major product.

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