Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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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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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?
Draw resonance contributors to show why pyridine-N-oxide is more reactive than pyridine toward electrophilic aromatic substitution. a. At what position does pyridine-N-oxide undergo electrophilic aromatic substitution?
Rank the following from LEAST TO MOST reactive towards electrophilic aromatic substitution:
1. p-Cresol, p-Toluidine, p-Chlorophenol, p-Chloroaniline
2. p-Hydroxybenzoic acid, p-Methoxybenzoic acid, p-Aminophenyl acetate, p-Methoxyphenyl acetate
Chapter 19 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
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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- Draw resonance contributors to show why pyridine-N-oxide is more reactive than pyridine toward electrophilic aromatic substitution.arrow_forwardRank group of compounds from most reactive to least reactive toward electrophilic aromatic substitution: :- benzene, benzoic acid, phenol, propylbenzenearrow_forwardThe 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 Phenolarrow_forward
- How do you account for the fact that N-phenylacetamide (acetanilide) is less reactive toward electrophilic aromatic substitution than is aniline? -NHCCH, -NH, N-Phenylacetamide (Acetanilide) Anilinearrow_forwardBoth 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.arrow_forwardList the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution: a. benzene, phenol, toluene, nitrobenzene, bromobenzene b. dichloromethylbenzene, difluoromethylbenzene, toluene, chloromethylbenzenearrow_forward
- Explain the reactivity and orientation effects observed in each heterocycle. a. Pyridine is less reactive than benzene in electrophilic aromatic substitution and yields 3-substituted products. b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields 2-substituted products.arrow_forwardExplain the reactivity and orientation effects observed in each heterocycle.a. Pyridine is less reactive than benzene in electrophilic aromatic substitution and yields 3-substituted products.b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields 2-substituted products.arrow_forwardTopic: Reactions of aromatic compoundsDraw a stepwise mechanism for the following reactionsarrow_forward
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