Answered: Explain why electrophilic aromatic…

Explain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in Pyridine it takes place at C-3 position?

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 19.82P: The following molecule undergoes an intramolecular reaction in the presence of pyrrolidinium...

See similar textbooks

Related questions

Q: Treatment of α,β-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a…

A: In this reaction, racemization of the methyl group linked to γ H is taking place. Racemization is a…

Q: a) Define saponification. b) The following reactivity order has been found for the saponification of…

Q: Which of the following is most susceptible towards nucleophilic aromatic substitution?

A: The aromatic nucleophilic substitution reaction follows addition elimination mechanism.

Q: Arrange the following radicals in order of decreasing rate of bromination. Justify your answer.

A: given arrange the following radicals in order of decreasing the rate of bromination. The…

Q: a) Which is more reactive towards Electrophilic aromatic substitution (EAS)? (b) Which of the…

A: Note: according to our guidelines we are supposed to answer only first three subparts. Kindly repost…

Q: Arrange the following carbonyl compounds in INCREASING REACTIVITY towards nucleophilic addition.

Q: Which product would be obtained if 3-methyl-2-butanol was used as the alcohol in the Electrophilic…

Q: :Explain the following Diazotization reaction carried out during the preparation of p-iodotoluene…

A: Diazotization reactions:

Q: 1) How will you describe whether any compound has been oxidized or reduced? Support the answer with…

A: Hi, we are supposed to answer one question. To get the remaining questions solved please mention the…

Q: Compound A was reacted with ozone (oxidative cleavage). The product formed was 5-oxohexanal…

Q: Friedel-Crafts acylation formed by attack at the meta positions of Nitrobenzene. (-NH2 and-OH) act…

A: In the Friedel-crafts acylation reaction, the electrophile is (RCO)+ that attacks the benzene ring…

Q: Hydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw the stereoisomers formed in this…

A: The formation of a cyclic hemiacetal is an acid catalyzed reaction. The cyclic hemiacetals formed by…

Q: The analgesic acetaminophen is synthesized by treating 4-aminophenol with one equivalent of acetic…

A: Given 4-aminophenol + acetic anhydride ----> acetaminophen + additional product

Q: 1) How will you describe whether any compound has been oxidized or reduced? Support your answer with…

A: Note: As per our guidelines, we are supposed to answer only one question. For other question to be…

Q: e) "Pyridine does not readily undergo electrophilic aromatic substitution, but it can undergo…

A: Interpretation - Briefly explain the statement and give the example of typical nucleophilic…

Q: The -NH, group is listed in our textbook as the strongest o,p-directing activator in electrophilic…

A: Given :

Q: Draw the major organic product of the reaction. Indicate the stereochemistry via wedge‑and‑dash…

A: In this question, we want to draw major product for this Reaction by using wedge‑and‑dash bonds. How…

Q: Rank imidazole, pyrrole, and benzene from most reactive to least reactive toward electrophilic…

A: Electrophilic substitution reaction- The replacement one atom or group of atom from reactant species…

Q: A. Arrange the following radicals in order of decreasing rate of bromination. Justify your answer.

Q: Which of the following statement(s) is(are) FALSE? a. Deactivating aryl groups decreases the energy…

A: The question is based on the concept of organic reactions. We have to explain the mechanism of…

Q: Arrange these compounds in order of reactivity towards electrophilic aromatic

A: The reactivity of aromatic compounds in electrophilic substitution reaction is depends on groups…

Q: When naphthalene undergoes an irreversible electrophilic aromatic substitution, such as a…

A: Alpha position is more stable than beta position because

Q: The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give…

A: (a) Here, the substitution does not occur on the ring which has a nitrogen atom since the lone pair…

Q: Treatment of α,β-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a…

A: In the reaction, racemization of a methyl group linked to gamma -carbon atom takes place. For…

Q: (a) Give a plausible explanation for each one of the following :(i) There are two – NH2 groups in…

A: It is a derivative of urea. Semicarbazide is the chemical compound with the formula OC. It is a…

Q: What specific electrophile is attacked by benzene when it undergoes nitration?

A: Electrophile means electron-loving species or we can say the species which is deficient in electrons…

Q: Only two of the following carbonyl-containing compounds have a large equilibrium onstant for…

Q: Nitration of aniline is carried out after acylation because :Select one a. O-and p-products are…

A: Given, Nitration of aniline is carried out after acylation because ? select one a). o- and…

Q: What product would result if you treated chloroacetyl chloride with an excess of diethylamine…

A: Here we have to say the name of product when chloroacetyl chloride treated with excess diethyl…

Q: Which ester, C or D, is more reactive in nucleophilic acyl substitution?Explain your reasoning.

Q: LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?

A: The full form of LDA is Lithium diisopropylamide. It has isopropyl groups create hindrance and make…

Q: Which of the following statements is FALSE? OA Bromobenzene is less reactive than benzene in an…

A: All the electron donating substituents on the ring activates the ring towards electrophilic aromatic…

Q: List TWO nucleophiles that would react with the epoxide belowwith the opposite regioselectivity…

A: Epoxides - Epoxide is an cyclic ether. The 3 membered ring unstable due to ring strain. The C-O…

Q: Give all possible and complete reaction for the following. Properly name the organic compound. 1.…

A: The naming of the organic compounds is done using the IUPAC rules. The possible and complete…

Q: subtitution is determined by the substituent which has a higher activation effect F, Cl, Br, and…

A: Statement 1 and statement 3 are false 1 Electron-withdrawing groups (EWGs) passivates the…

Q: Predict the most likely sites of electrophilic aromatic substitution in each of the following…

A: Predict the most likely sites of electrophilic aromatic substitution in the above molecules are…

Q: Provide the complete mechanism using Curved Arrow Formalism for the reaction of…

A: Please find the attachment.

Q: Identify the ring which is more reactive towards electrophilic aromatic substitution.

A: Electrophiles are electron deficient system that are attracted to electron system. Electrophilic…

Q: The analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate…

A: The most acidic proton in compound A will be the one which is attached to the carbon adjacent to the…

Q: Propose a synthesis for propoxyphene from 1-phenyl-1-propanone and any other necessary reagents.

Q: (a) Why are alkyl halides insoluble in water? (b) Why is Butan-l-ol optically inactive but…

A: Chirality and thereby the optical isomerism in organic compounds is caused by the presence of…

Q: What is the mechanism of vanillin esterification to vanillyl acetate under basic conditions (NaOH),…

Q: Between Acetone and Acetyl chloride ,which kind of carbonyl compound has the more electrophilic…

A: The structure of the Acetone and Acetyl chloride is as follows: The electronegativity of the oxygen…

Q: Explain why the halogens, when attached to a benzene ring, weakly deactivate the ring toward…

A: Halogens bonded to benzene ring has three lone pairs. These three electron pairs can cause resonance…

Q: Draw a curved arrow mechanism for the oxidation of cyclohexanol with the product from the…

A: Applying concept of organic synthesis and application of.reagent.

Question

1) Explain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in Pyridine it takes place at C-3 position?

2) LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?

3) List the following esters in order of decreasing reactivities towards hydrolysis with reason:
Methyl benzoate, p-cyano methyl benzoate and p-hydroxy methyl benzoate

Study of body parts and their functions. In this combined field of study, anatomy refers to studying the body structure of organisms, whereas physiology refers to their function.

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

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

1) How will you describe whether any compound has been oxidized or reduced? Support the answer with suitable examples. 2)Why carboxylic acid with a carbonyl group at 3rd position can be decarboxylated? 3) Explain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in Pyridine it takes place at C-3 position? 4) List the following esters in order of decreasing reactivities towards hydrolysis with reason: Methyl benzoate, p-cyano methyl benzoate and p-hydroxy methyl benzoate 5)LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?
Explain why pentane-2,4-dione forms two alkylation products (A and B) when the number ofequivalents of base is increased from one to two.
What reaction conditions—base, solvent, and temperature—are needed to convert ketone A to either B or C by an intramolecular alkylation reaction?
Draw the principal organic product for the reaction of 2-bromobutane with magnesium in diethyl ether, followed with benzaldehyde in diethyl ether, and then followed by dilute acid...
Rank imidazole, pyrrole, and benzene from most reactive to least reactive toward electrophilic aromatic substitution.
Why aldehydes and ketones do not undergo nucleophilic substitution reaction?
a) Give the mechanism for the following regioselectie allylation reaction. Answer the question with the arrow: b) Give both structures and IUPAC names of the reactants for the compound below formed via a crossed aldol reaction with KOH as promotor. Explain why only one product is formed.
Rank the following esters in order of decreasing reactivity in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate):Rank the same esters in order of decreasing reactivity in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).
Explain why pentane-2,4-dione forms two different alkylation products (A or B) when the number of equivalents of base is increased from one to two.
Thioester hydrolysis yielding more energy than O-ester hydrolysis is ultimately due to Bond between S and carbonyl carbon is of lower energy Thioesters are more resonance stabilized Products of O-ester hydrolysis have lower degree of solvation than its reactants in water Sulphur being a larger atom than oxygen
Explain why benzaldehyde is less reactive than cyclohexanecarbaldehyde toward nucleophilic attack.
Draw the main organic product formed in each of the following reactions: