Pearson eText Organic Chemistry -- Instant Access (Pearson+)

8th Edition

ISBN: 9780135213711

Author: Paula Bruice

Publisher: PEARSON+

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Textbook Question

Chapter 19.5, Problem 7P

Explain why cyclopentadiene (pK_a = 15) is more acidic than pyrrole (pK_a - 17), even though nitrogen is more electronegative than carbon.

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Chapter 19.5, Problem 6P

Chapter 19.5, Problem 8P

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Chapter 19 Solutions

Pearson eText Organic Chemistry -- Instant Access (Pearson+)

Ch. 19.1 - Name the following:Ch. 19.2 - Prob. 3P Ch. 19.2 - Prob. 4P Ch. 19.3 - Draw the product of each of the following...Ch. 19.5 - Prob. 6P Ch. 19.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 19.5 - When pyrrole is added to a dilute solution of...Ch. 19.6 - Prob. 10P Ch. 19.6 - How to the mechanisms of the following reactions...Ch. 19.6 - Prob. 12P

Ch. 19.6 - Rank the following compounds from easiest to...Ch. 19.7 - Prob. 14P Ch. 19.7 - Prob. 15P Ch. 19.7 - Prob. 16P Ch. 19.7 - Prob. 17P Ch. 19.7 - Prob. 18P Ch. 19.7 - Prob. 19P Ch. 19.7 - Prob. 20P Ch. 19 - Name the following:Ch. 19 - Prob. 22P Ch. 19 - Rank the following compounds from strongest acid...Ch. 19 - Which of the following compounds is easier to...Ch. 19 - Rank the following compounds from most reactive to...Ch. 19 - One of the following compounds undergoes...Ch. 19 - Benzene undergoes electrophilic aromatic...Ch. 19 - Pyrrole reacts with excess...Ch. 19 - The dipole moments of furan and tetrahydrofuran...Ch. 19 - Name the following:Ch. 19 - Prob. 31P Ch. 19 - Prob. 32P Ch. 19 - a. Draw resonance contributors to show why...Ch. 19 - The chemical shifts of the C-2 hydrogen in the...Ch. 19 - Explain why protonating aniline has a dramatic...Ch. 19 - Prob. 36P Ch. 19 - Propose a mechanism for the following reaction:Ch. 19 - Prob. 38P Ch. 19 - Propose a mechanism for the following reactions:Ch. 19 - Prob. 40P Ch. 19 - Prob. 41P Ch. 19 - Prob. 42P Ch. 19 - Organic chemists work with tetraphenylporphyrins...Ch. 19 - Show how the following compounds can be prepared...

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Explain why cyclopentadiene (p K a = 15) is more acidic than pyrrole (p K a - 17), even though nitrogen is more electronegative than carbon.

Solution Summary: The author explains why cyclopentadiene is more acidic than pyrrole because on losing a hydrogen ion, compound changes into stable aromatic compound.

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Chapter 19 Solutions