Below is the elimination reaction of 4-fluoro-4-(4-nitrophenyl)butan-2-one forming 4-(4- nitrophenyl)but-3-en-2-one. ore F base F- O,N O2N' Two sets of experiments were carried out with different reactants as shown below. The k#/kp values are also given below. (L is either Hydrogen, H OR Deuterium, D) Set 1 k#/kp = 3.7 Set 2 kµ/kp = 1.5 a) Even though Sets 1 and 2 show two different kinetic isotope effect values, both reactions took place via the SAME mechanism. Propose ONE mechanism that would explain both observations in Sets 1 and 2. Explai your answer.

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Below is the elimination reaction of 4-fluoro-4-(4-nitrophenyl)butan-2-one forming 4-(4-
nitrophenyl)but-3-en-2-one.
base
F-
O2N
O,N
Two sets of experiments were carried out with different reactants as shown below. The k /kp
values are also given below.
(L is either Hydrogen, H OR Deuterium, D)
Set 1
O,N
kH/kp = 3.7
Set 2
O,N
kH/kp
= 1.5
a) Even though Sets 1 and 2 show two different kinetic isotope effect values, both
reactions took place via the SAME mechanism.
Propose ONE mechanism that would explain both observations in Sets 1 and 2. Explain
your answer.
b) Suggest another modification on the experiment to further support your above proposal
Transcribed Image Text:Below is the elimination reaction of 4-fluoro-4-(4-nitrophenyl)butan-2-one forming 4-(4- nitrophenyl)but-3-en-2-one. base F- O2N O,N Two sets of experiments were carried out with different reactants as shown below. The k /kp values are also given below. (L is either Hydrogen, H OR Deuterium, D) Set 1 O,N kH/kp = 3.7 Set 2 O,N kH/kp = 1.5 a) Even though Sets 1 and 2 show two different kinetic isotope effect values, both reactions took place via the SAME mechanism. Propose ONE mechanism that would explain both observations in Sets 1 and 2. Explain your answer. b) Suggest another modification on the experiment to further support your above proposal
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