17. In the following reaction, it was found by isotope scrambling experiments that the acid and the water add to the alkene in a single step. Hence, the More O'Ferrall-Jencks plot shows a diagonal that represents this single-step process. The other pos- sible competing mechanisms involve intermediates placed on the other corners of this diagram. Explain what happens to the extent of protonation in the transition state of the single-step process if the strength of the acid is increased. What hap- pens to the extent of nucleophilic attack at the transition state as the acid strength is increased? Does your result seem rea- sonable? Explain. НА O. НА

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
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Problem 36E
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17. In the following reaction, it was found by isotope scrambling experiments that the acid and the water add to the alkene in a
single step. Hence, the More O'Ferrall-Jencks plot shows a diagonal that represents this single-step process. The other pos-
sible competing mechanisms involve intermediates placed on the other corners of this diagram. Explain what happens to
the extent of protonation in the transition state of the single-step process if the strength of the acid is increased. What hap-
pens to the extent of nucleophilic attack at the transition state as the acid strength is increased? Does your result seem rea-
sonable? Explain.
НА
O.
НА
H,0
Transcribed Image Text:17. In the following reaction, it was found by isotope scrambling experiments that the acid and the water add to the alkene in a single step. Hence, the More O'Ferrall-Jencks plot shows a diagonal that represents this single-step process. The other pos- sible competing mechanisms involve intermediates placed on the other corners of this diagram. Explain what happens to the extent of protonation in the transition state of the single-step process if the strength of the acid is increased. What hap- pens to the extent of nucleophilic attack at the transition state as the acid strength is increased? Does your result seem rea- sonable? Explain. НА O. НА H,0
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