Pyridine N-oxides can also react in electrophilic aromatic substitutions. In the reaction below, only a single product is obtained. Use resonance structures to justify the selective formation of this product. NO2 HNO3 H,SO4

Pyridine N-oxides can also react in electrophilic aromatic substitutions. In the reaction below, only a single product is obtained. Use resonance structures to justify the selective formation of this product. NO2 HNO3 H,SO4

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

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.40P: Enamines normally react with methyl iodide to give two products: one arising from alkylation at...

See similar textbooks

Related questions

Q: For the Electrophilic Aromatic Substitution lab you performed an iodination reaction on salicylamide…

Q: Which is more stable - a phenyl radical, [C6H5]•, or a benzyl radical, [C6H5CH2]• - and why?

Q: Redraw the structure of indigo below with explicit double bonds drawn in the aromatic rings. Now…

A: This condition that arises when two systems are "linked together," such as double bonds is called…

Q: 1 page 2. Name these aromatic compounds properly. a) b) Br 4. Write in the reagents need to…

Q: CH3 Br2/FeBr3 C3H,BrO 6. C) Using resonance structures, justify whether the acetyl group of compound…

A: The answer is given as follows

Q: Write the structure of the major organic product isolated from the reaction of 3-hexyne with (a)…

A: Note: Since you have posted a question with multiple subparts, we will solve the first three sub…

Q: 4.85 deche 7.5 7.0 2.04 2.05 2.93 5.0 4.5 4.0 3.5 3.0 2.5 2.0 (c)

Q: ÇHCH3 1. КMпОд, сalor 1. SOC, 2. Hо 2. ELOH H;CHCH2Č

A: The question is based on the concept of organic reactions. we have to identify the Product formed…

Q: Aromatics can be converted into nitroaromatics upon treatment with a mixture of nitric and sulfuric…

Q: Where does the indicated aromatic system undergo electrophilic substitution? NO2 iv i ii CO2M. ii

A: Aromatic electrophilic substitution occurs at the site where the electron density is maximum.…

Q: 9. Which of the following would you expect to be anti-aromatic? :0: II IV V. III 9. Which of these…

A: The system to be an aromatic system must follow Huckel's Rule of Aromaticity which is given as -…

Q: Aniline reacts with bromine in the absence of a Lewis acid to give monosubstitution products. Draw a…

A: Electrophilic aromatic substitution reactions are those reactions in which replacement of positively…

Q: Of the four possible cis,trans isomers, one is formed in over 85% yield. Q.) Which is the structure…

A: Given:

Q: The compound MON-0585 is a nontoxic, biodegradable larvicide that is highly selective against…

Q: Predict the most likely site of attack in electrophilic aromatic substitution. (m) OCH, (b) OH (c)…

A: Electron density and steric factor govern the site for the attack by an electrophile. Greater the…

Q: 2H2 CH,CH,CH,C=CCH3 Lindlar Pd Give the structure of the ommited in the reaction|

Q: Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the…

A: The major products of the reactions of naphthalene with HNO3, H2SO4 is predicted as follows,

Q: Predict the product formed in the nucleophilic aromatic substitution reaction between…

A: Nucleophilic Aromatic Substitution Reaction : is a Substitution reaction in which the nucleophile…

Q: Is any other acid good for catalyze nitration to aromatic ? The textbook use sulfuric acid as…

A: A question based on introduction to organic chemistry that is to be accomplished.

Q: 3. Consider the following carboxylic acid (propanoic acid) and answer the question that follows:…

A: Since you have posted a question with multiple subparts, we will solve first three subparts for you.…

Q: to CH;CH,OH Br Major Minor Nucleophilic substitution mechanism:

Q: Q4. Discuss the reagents, conditions, and mechanism of the following reactions. a) Kolbe Reaction b)…

Q: O: C14H1206 maleic anhydride in excess

A: The reaction in which conjugated diene react with dienophile is known as Diels alder reaction.

Q: Provide the major aromatic product(s) for the reactions below. so, H,50, KMno, NaOM H20, heat NaH,…

Q: Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the…

A: The reaction of cyclohexanol with Lewis acid BF3 would be given as, The above step is the first…

Q: Please help

A: The resonance structures of N-pyridine N-oxide are,

Q: The C‚N triple bond in acetonitrile has a dipole moment of about 3.6 D and a bond length of about…

A: Dipole moments are present between two atoms or ions of different electronegativities. The extend of…

Q: How you can synthesize methylacetylene (at least two methods). Write reactions of methylacetylene…

A: Methyl acetylene is C3H4, three Carbon in a chain containing one single C-C bond and a triple C-C…

Q: The compound MON-0585 is a non-toxic, biodegradable larvicide that is highly selective against…

A: In organic synthesis, different reagent converts the reactant into target products. These reagents…

Q: Terminal alkynes react with Br2 and water to yield bromo ketones. For example: Br2, H20 CH2Br…

A: Alkyne gives an electrophilic addition reaction with bromine water to form alpha bromoketone.

Q: Give the structures of the substitution products expected when 1-bromohexane reacts with(a)…

A: There are many mechanisms in organic chemistry such as nucleophilic substitution, nucleophilic…

Q: The deuterium kinetic isotope effect for the halogenation of an alkane is defined in the following…

A: The rate of homolytic cleavage of C – H bond by X will depend upon the reactivity of the radical X…

Q: ÇHCH3 1. KMNO4, calor 1. SOCh 2. H30 2. ELOH H3CHCH2Č

A: Alkyl benzene on reaction with hot kmno4 gives conversion of alkyl fragments to acid(COOH).…

Q: What type of reaction is this? Br H + Br + H20 OÖ-H O SN1 O SN2 E1 E2 O Nucleophilic aromatic…

A: Answer

Q: The following product is expected from the reaction of 3-heptyne with sodium metal in liquid…

Q: ophilic aromatic substitutions proceed in two stages. 1. Attack of the aromatic ring on the…

A: Here the step 1 Is generation of an electrophile which is generated as the Br-Br bond interact with…

Q: Compound name is Toluene . Name the structures of all possible chemical (Electrophilic aromatic…

A: All the reaction schemes are shown below including name and structure of all the products. The…

Q: Propose a structure for an aromatic hydrocarbon, C3H10, that can form three C3HgBr products on…

A: The molecular formula of the aromatic hydrocarbon given is C8H10.

Q: Does perchlorate (ClO4-) have an extremely low nucleophilicity because it participates in a lot of…

Q: Predict the major product(s) of electrophilic aromatic substitution

A: Electrophilic aromatic substitution is a chemical reaction in which the electrophile attacks the…

Q: AICI, Ph 3. Rank the following aromatic species in order Crafts alkylation with t-butanol. (-0…

A: Friedel craft alkylation is electrophilic substitution reaction . In this benzene act as nucleophile…

Q: Q6

A: Chlorination of alkenes in presence of UV light undergoes substitution reaction. The reaction…

Q: Place the following in order of reactivity towards electrophilic aromatic substitution. NO COCH, OH…

A: Aromatic electrophilic substitution reaction: Aromatic electrophilic substitution reactions are the…

Q: Which site in the molecule below is most reactive in electrophilic aromatic substitution? (а) OH (b)…

A: Answer:- This question is answered by using the simple concept of directive effect of disubstituted…

Q: (a) In an acid-catalyzed hydration, one of the following 10 carbon alkynes is expected to produce a…

A: (a) An alkyne produces a ketone on acid catalysed hydration.

Q: Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the…

A: Given reaction,

Q: Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the…

A: Naphthalene undergoes electrophilic aromatic substitution in the first position. The structure of…

Q: Acetonitrile (CH3CN) has resonance at 1.97 ppm, whereas methyl chloride (CH3Cl) has resonance at…

A: Given Molecule CH3CN Dipole Moment = 3.92 D CH3Cl Dipole Moment = 1.85 D CH3CN Proton resonance…

Q: For the compound p-anisidne 2. Name and draw the structures of all possible chemical (Electrophilic…

A: We have to write the all reactions

Q: Of the four possible cis,trans isomers, one is formed in over 85% yield. Q.) Draw structural…

A: Geometric isomers: Two atoms with the same side location of the double bond are called cis isomers…

Question

Pyridine N-oxides can also react in electrophilic aromatic substitutions. In the reaction
below, only a single product is obtained. Use resonance structures to justify the selective
formation of this product.
NO2
HNO3
H2SO4

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

General Physical Properties of Organic Compounds

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with HNO3, H2SO4 (b) Br2, FeBr3
OOn a reaction with acid, 4-pyrone is protonated on the carbonyl-group oxygen to give a stable cationic product. Using resonance structures and the Huckel 4n+2 rule, explain why the protonated product is so stable. 4-Pyrone
Predict the product formed in the nucleophilic aromatic substitution reaction between 1-chloro-2,4-dinitrobenzene and sodium methoxide (NaOCH3). Draw the mechanism for the reaction, showing why the product you have selected is formed.
Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with cyclohexanol and BF3
Nucleophilic substitution happens on compounds having nucleophilic groups as leaving groups. The rule is, the weaker the basicity of a group of the substrate, the better is its leaving ability. In these substitution reactions, the basicity of leaving group must be less than the incoming nucleophilic group. Nucleophilic substitution reaction at sp3-hybridized carbon is either bimolecular (SN2) or unimolecular. Bimolecular reaction takes place in single step, involving transition state intermediate. In SN2 reaction, inversion in configuration occurs. In case of optically active alkyl halides, the inversion in configuration is called Walden inversion. SN2 reaction is preferred if the compound has less steric hindrance. On the other hand, unimolecular (SN1) reaction involves two steps and a carbonium ion intermediate. Optically active substrates give racemic mixture in these type of reactions. Which of the following will produce enantiomeric pair on treatment with HOH? " I ÇH, C,Hs-C-Br…
Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.
Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.
When 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%
Treatment of anthranilic acid with nitrous acid gives an intermediate, A, that contains a diazonium ion and a carboxylate group. When this intermediate is heated in the pres- ence of furan, a tricyclic compound is formed. Propose a structural formula for com- pound A and a mechanism for the formation of the tricyclic product. COOH NANO, HCI + CO, + N2 NH2 Anthranilic acid
What is the structural requirement for a substance to react with ammoniacal AgNO3? Why would acetylene react with Tollen's reagent but not cyclohexane or cyclohexene?
b) Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OMe HO + OMe + OH HO + CH; OH
Aromatic substitution can be done on naphthalene. Treatment of naphthalene with concentrated H2SO4 gives two (and only two) different sulfonic acids.