Answered: Q9: Explain why compound I is…

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Q9: Explain why compound I is protonated on O while compound II is protonated on N. NH2 NH2 I II

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter4: Acids And Bases

Section: Chapter Questions

Problem 4.48AP: As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more...

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Q9: Explain why compound I is protonated on O while compound II is protonated on N.
NH2
NH2
I
II

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As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone.
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Q9: Explain why compound I is protonated on O while compound II is protonated on N. NH2 DD I II NH2
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