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

Chapter8: Addition Via Carbocation

Section: Chapter Questions

Problem 4E: Draw the complete mechanism of each pair of reactants including any favorable rearrangements and all...

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