Pyridine undergoes electrophilic aromatic substitution preferentially at the 3 position asillustrated by the synthesis of 3-nitropyridine.NO2H,SO,+ HNO3+ H2O300°CPyridine3-NitropyridineUnder these acidic conditions, the species undergoing nitration is not pyridine, but itsconjugate acid. Write resonance contributing structures for the intermediate formedby attack of NO,+ at the 2, 3, and 4 positions of the conjugate acid of pyridine. Fromexamination of these intermediates, offer an explanation for preferential nitration at the3 position.

Answered: Image /qna-images/answer/3d4beeb9-9c7c-43b6-9015-a0744430d5a6.jpg

Answered: Pyridine undergoes electrophilic…

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

Chapter22: Reactions Of Benzene And Its Derivatives

Section: Chapter Questions

Problem 22.63P

See similar textbooks

Similar questions

Pyridine undergoes electrophilic aromatic substitution preferentially at the 3 position as illustrated by the synthesis of 3-nitropyridine. Under these acidic conditions, the species undergoing nitration is not pyridine, but its conjugate acid. Write resonance contributing structures for the intermediate formed by attack of NO2+ at the 2, 3, and 4 positions of the conjugate add of pyridine. From examination of these intermediates, offer an explanation for preferential nitration at the 3 position.
Starting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.)p-Chlorobenzoic acid
Starting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.) m-Chlorobenzoic acid
In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?
Arrange these compounds in order of reactivity towards electrophilic aromaticsubstitution, with the most reactive compound listed first
Phenols are less acidic than carboxylic acids, with values of pKa around 10. Phenols aredeprotonated by (and therefore soluble in) solutions of sodium hydroxide but not by solutions of sodium bicarbonate. Explain how you would use extractions to isolate the three purecompounds from a mixture of p-cresol (p-methylphenol), cyclohexanone, and benzoic acid.
Rhodamine B is useful dye prepared in a manner very similar to fluorescein. Due to the nitrogen donating groups, rhodamine B absorbs 550 nm light and fluoresces 580 nm light. Provide a detailed mechanism for the formation of Rhodamine B from m-(diethylamino)phenol and phthalic anhydride in the presence of acid and heat.
Furan undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient.For example, furan reacts with bromine to give 2-bromofuran.(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms ofeach sigma complex, and compare their stabilities.(b) Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.O Br O123furan 2-bromofuran
Acetoxybenzene (PhOC(=O)OCH3) is much less reactive than ethoxybenzene (PhOCH2CH3) in electrophilic aromatic substitution reactions. Suggest an explanation for this result, based on an analysis of the inductive and resonance electronic effects of the two substituents on the stability of theWheland intermediate for para substitution by an electrophile E+
Rank the following carboxylic acids derivatives based on their reactivity towards nucleophiles (1-most reactive - 4- least reactive), and describe the structural features you use to detrmine your ranking.
compare reactivity of the compound below to that of benzene in electrophilic aromatic substitution.
(a) Write the structures of main products when benzene diazonium chloride reacts with the following reagents :(i) H3PO2 + H2O (ii) CuCN/KCN (iii) H2O(b) Arrange the following in the increasing order of their basic character in an aqueous solution :C2H5NH2, (C2H5)2NH, (C3H5)3N(c) Give a simple chemical test to distinguish between the following pair of compounds :C6H5—NH2 and C6H5—NH—CH3

SEE MORE QUESTIONS

Recommended textbooks for you

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

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

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

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

Publisher:

Cengage Learning

SEE MORE TEXTBOOKS