Organic Chemistry - Access
7th Edition
ISBN: 9780321820020
Author: Bruice
Publisher: PEARSON
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Chapter 20, Problem 38P
- a. Draw resonance contributors to show why pyridine-N-oxide is more reactive than pyridine toward electrophilic
aromatic substitution. - b. At what position does pyridine-N-oxide undergo electrophilic aromatic substitution?
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Explain why acetanilide is less reactive toward electrophilic substitution than aniline.?
In the electrophilic aromatic substitution reaction of acetanilide with bromine, is an intermediate resonance stabilized carbocation formed? Why or why not? Bromine is dissolved in glacial acetic acid.
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Explain why protonating aniline has a dramatic effect on the compound’s UV spectrum, whereas protonating pyridine has only a small effect on that compound’s UV spectrum.
Chapter 20 Solutions
Organic Chemistry - Access
Ch. 20.1 - Name the following:Ch. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Draw the product of each of the following...Ch. 20.5 - Prob. 6PCh. 20.5 - When pyrrole is added to a dilute solution of...Ch. 20.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 20.6 - Prob. 10PCh. 20.6 - How to the mechanisms of the following reactions...Ch. 20.6 - Prob. 12P
Ch. 20.6 - Rank the following compounds from easiest to...Ch. 20.7 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.7 - Prob. 16PCh. 20.7 - Prob. 17PCh. 20.7 - Prob. 18PCh. 20.7 - Prob. 19PCh. 20.7 - Prob. 20PCh. 20 - Name the following:Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Which of the following compounds is easier to...Ch. 20 - Rank the following compounds from most reactive to...Ch. 20 - One of the following compounds undergoes...Ch. 20 - Benzene undergoes electrophilic aromatic...Ch. 20 - The dipole moments of furan and tetrahydrofuran...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - The chemical shifts of the C-2 hydrogen in the...Ch. 20 - Explain why protonating aniline has a dramatic...Ch. 20 - Prob. 33PCh. 20 - Propose a mechanism for the following reaction:Ch. 20 - Prob. 35PCh. 20 - Propose a mechanism for the following reactions:Ch. 20 - Prob. 37PCh. 20 - a. Draw resonance contributors to show why...Ch. 20 - Prob. 39PCh. 20 - Pyrrole reacts with excess...Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Organic chemists work with tetraphenylporphyrins...
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