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
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ISBN:9780618974122
Author:Andrei Straumanis
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Chapter23: Addition To A Carbonyl
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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
?
Transcribed Image Text: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 ?
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