Problem: Consider the reaction shown below. (a) Draw all four carbocation intermediates possible from protonation of the diene. Don't forget to include any resonance structures! (b) Identify the most stable carbocation intermediate and explain why it is the most stable. (c) Draw the arrows for the first step of the mechanism to show the formation of the most stable carbocation intermediate. (d) Draw the alcohol product(s) formed by attack of water on the most stable carbocation intermediate. (e) Draw the arrows to show how one alcohol product is formed from the carbocation. Include intermediates, as needed. (f) Which of the alcohol products would you expect to be formed in the greatest amount at low temperatures? Explain. (g) Which of the alcohol products would you expect to be formed in the greatest amount at high temperatures? Explain. H2SO4 H₂O ?
Problem: Consider the reaction shown below. (a) Draw all four carbocation intermediates possible from protonation of the diene. Don't forget to include any resonance structures! (b) Identify the most stable carbocation intermediate and explain why it is the most stable. (c) Draw the arrows for the first step of the mechanism to show the formation of the most stable carbocation intermediate. (d) Draw the alcohol product(s) formed by attack of water on the most stable carbocation intermediate. (e) Draw the arrows to show how one alcohol product is formed from the carbocation. Include intermediates, as needed. (f) Which of the alcohol products would you expect to be formed in the greatest amount at low temperatures? Explain. (g) Which of the alcohol products would you expect to be formed in the greatest amount at high temperatures? Explain. H2SO4 H₂O ?
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter23: Addition To A Carbonyl
Section: Chapter Questions
Problem 10E
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