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.

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Answered: Pyridine undergoes electrophilic…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter20: Carboxylic Acids And Nitriles

Section20.SE: Something Extra

Problem 54AP

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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.
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?
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.
Describe the trends in the acidityand physical properties of carboxylicacids, and explain how their acidityvaries with their substituents.
Show how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.
(b) State the reagents needed to convert benzoic acid into the following compounds. (i) C6H§COCI (ii) C,H$CH2OH (iii) C6H$CONHCH3
The 1H- and 13C-NMR data of an ester of molecular formula C6H10O2 are given below. Also shown are the COSY and HETCOR NMR spectra of the ester. Draw the structure of the ester, explaining how you reach your conclusion. 1H-NMR: 7.20-6.90 (1H), 5.85 (1H), 4.16 (2H), 1.88 (3H), 1.31 (3H) ppm 13C-NMR: 166.7, 144.5, 123.0 , 60.2, 18.0, 14.3 ppm
Arrange the following reagents in INCREASING order of * nucleophilicity* in protic solvent: NaOCH, NaSCH, CH;OH CH,SH CH;CO,H Next arrange them in increasing order of nucleophilicity in aprotic solvent. Next arrange them in increasing order of basicity. Explain any differences between the different orderings.
Discovery of the antibiotic sulphanilamide led to rapid development of a large number of structurally related sulphonamides. Some of these were useful leads to compounds with other medicinal properties. Amongst these, sulfasalazine was active in the treatment of ulcerative colitis, a potentially fatal disease of the colon. As a medicinal chemist, you are about to carry out the synthesis of sulfasalazine, starting from aniline. Give the chemical names and draw the chemical structures of the reagents you will need to use for the all the steps marked (a)-(d). Aniline HO₂C HO (a) N=N- ACHN Ac represents CH3CO Sulfasalazine SO,NH S0,C1 N (b) (d) H₂N- SO,NH (c) N [Oro] SO,NH N Step (a) in question 5 above results in the para product only. Explain why this occurs.
Propose single-step and multistep syntheses of acid derivatives from compoundscontaining other functional groups. Propose multistep syntheses using acid derivatives as starting materials and intermediates.
2- Arrange the following compounds in the approximate order of their basicity toward 5% hydrochloric acid solution: Diphenylamine, benzylamine, 4-methylaniline, benzamide
(b) Predict the major product (or products) formed when each of the following compounds 11- 14 reacts with a mixture of concentrated HNO3 and H2SO4. CO2H HN CO2H CI 11 12 13 14 (c) Pick one of the reactions under (b) and write the mechanism of the electrophilic aromatic substitution in detail (generation of the attacking electrophile is not required).

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