EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 19, Problem 33P
- 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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Students have asked these similar questions
Both pyridine and pyrrole are nitrogen containing aromaticheterocyclic compounds. When treated with HCI, only pyridine forms a
hydrochloride salt, whereas pyrrole is unreactive Which of the following is not a valid explanation for this observed reactivity?
pyridine
ругrole
O The lone pair on pyridine is not part of the aromatic system.
O The lone pair on pyridine can be protonated without disrupting the aromatic stability.
O The lone pair on pyrrole is sp hybridized and is less prone to protonation.
O Protonation of pyrrole leads to a nonaromatic cation, which is less stable
O The lone pair on pyrrole is involved in making the compound aromatic and thus is less susceptible to protonation.
Rank group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
:- benzene, benzoic acid, phenol, propylbenzene
The order of increasing acidity is
Phenol < meta-cyanophenol < ortho-cyanophenol
1.how about para-cyanophenol??does it has higher acidicity than both ortho-cyanophenol and meta cyanophenol or lower??
2.why does ortho-cyanophenol have higher acidicity than meta cyanophenol??
3. why doesmeta cyanophenol have higher acidicity than Phenol
Chapter 19 Solutions
EBK ORGANIC CHEMISTRY
Ch. 19.1 - Name the following:Ch. 19.2 - Prob. 3PCh. 19.2 - Prob. 4PCh. 19.3 - Draw the product of each of the following...Ch. 19.5 - Prob. 6PCh. 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. 10PCh. 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. 14PCh. 19.7 - Prob. 15PCh. 19.7 - Prob. 16PCh. 19.7 - Prob. 17PCh. 19.7 - Prob. 18PCh. 19.7 - Prob. 19PCh. 19.7 - Prob. 20PCh. 19 - Name the following:Ch. 19 - Prob. 22PCh. 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. 31PCh. 19 - Prob. 32PCh. 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. 36PCh. 19 - Propose a mechanism for the following reaction:Ch. 19 - Prob. 38PCh. 19 - Propose a mechanism for the following reactions:Ch. 19 - Prob. 40PCh. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - Organic chemists work with tetraphenylporphyrins...Ch. 19 - Show how the following compounds can be prepared...
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