14. Explain why pyrrole is an electron-rich heterocycle that is activated toward electrophilic aromatic substitution, while pyridine is an electron poor heterocyclic that is deactivated toward electrophilic aromatic substitution.

14. Explain why pyrrole is an electron-rich heterocycle that is activated toward electrophilic aromatic substitution, while pyridine is an electron poor heterocyclic that is deactivated toward electrophilic aromatic substitution.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 7CTQ

See similar textbooks

Related questions

Q: .CH3 NH3 (a) I or II `NH2 (b) I or II IZ:

A: Concept used here: Rate of EAS is directly proportional to electron donating group (electron rich).…

Q: Which carbon will be the best site for electrophilic aromatic substitution? A

Q: Which carbonyl is more suceptible to nucleophilic attack, carbonyl of cyclohexanone or carbonyl of…

A: The two carbonyl compounds given are hexanal and cyclohexanone.

Q: Which reaction product (A or B) is more likely to form in the epoxide ring opening reaction?…

Q: From 1 being the slowest and 4 being the fastest rank the aromatic hydrocarbons in terms of…

A: The compounds given are,

Q: In regards to alpha carbons: Why are hydrogens alpha carbons acidic? Provide an example to show how…

A: Given, Nature of the carbon = alpha carbon alpha carbon is the carbon next to the functional group…

Q: Arrange these leaving groups in order of increasing E2 reaction rate.

A: Here among the leaving groups , the weaker the base , more is its ability to leave . They have…

Q: Explain why a methoxy group (CH3O) increases the rate of electrophilic aromatic substitution, but…

A: Methoxy group (CH3O) increases the rate of the rate of electrophilic aromatic substitution reaction,…

Q: Rank the following according to increasing reactivity with 1 as the least reactive, and 4 as the…

A: The reactivity order for nucleophilic acyl substitution is as follows:

Q: Draw the reactivity series for nucleophilic substitution at the carbonyl carbon. (You may exclude…

A: Reactivity series for nucleophilic substitution at the carbonyl carbon?

Q: If squalene is synthesized in a medium containing acetate with a 14C-labeled carbonyl carbon, which…

Q: Which carbon will be the best site for electrophilic aromatic substitution? A C

Q: Quinolines and isoquinolines which has a greater electrophilic aromatic substitution reactivity

A: Quinoline Iso-quinoline

Q: Which reacts fastest & slowest with m-chloroperbenzoic acid, why?

A: We know that The mCPBA is peroxy acid it react with alkene to form epoxide. the electrophilic…

Q: Which benzene derivative would be the most reactive in an electrophilic aromatic substitution…

Q: Attached compounds undergoes E2 elimination with strongbase? For compounds that undergo elimination,…

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

A: Alpha position is more stable than beta position because

Q: Which is the better retrosynthesis for the given target molecule? Explain, and provide a one-step…

A: E option is correct.

Q: Why is bond B longer than bond A in the given protonated epoxide?

A: Given a protonated epoxide:

Q: The following molecule contain two aromatic rings.Which ring in each undergoes electrophilic…

A: Organic reactions are mainly classified into nucleophilic substitution reactions and electrophilic…

Q: Explain why compound A does not undergo an E2 elimination with strong base.

A: For the structure to be more stable it has to have the bulky phenyl group in the equtorial position.…

Q: Devise a synthetic strategy to complete the following transformation. HOʻ

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

Q: Explain why one of the following molecules will undergo an E1 elimination faster:

A: In the E1 reaction the elimination of leaving group first and then deprotonation takes place finally…

Q: Under all conditions of epoxide ring-opening, the rate-determining step is always: Select one: A.…

Q: What aldol product is formed when two molecules of butanal react together in the presence of base?…

A: Treatment of butanal in the presence of strong base forms a resonance-stabilized enolate ion, which…

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: Why is the nitro group a meta director? Select one: O a. Because it adds electron density to the…

A: 1. Nitro is electron withdrawing group. It will remove electron density from o, p positions.…

Q: Why is the carbon bonded to halogen electrophilic? Indicate with arrows the direction of…

A: Carbon is less electronegative than halogen atom. Halogen atom has greater tendency to attract…

Q: How can we explain why, in base-catalyzed halogenation of acetone, the second (and third)…

A: Halogens are 7th group elements and their introduction into organic compounds via substitution gives…

Q: Explain the major step of a nucleophilic acyl substitution ?

A: The functional groups that undergo nucleophilic acyl substitutions are called carboxylic acid…

Q: What is the appropriate compound of the picture via Wittig reaction?

A: Organophosphorus ylides react with aldehydes or ketones to give substituted alkenes in a…

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: Which one would be most reactive toward electrophilic aromatic substitution?

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

Q: Unsaturated carbonyl compounds are susceptible to either 1,2 addition or 1,4 (Michael) addition.…

Q: How would the other substituents on metal would affect the stability of the metal alkylidenes?

A: Metal alkylidenes are the organometallic compounds that have a metal carbon double bond, and have…

Q: What aldol product is formed when two molecules of butanal react together in the presence of base?…

A: 1-Butanal has the molecular formula CH3-CH2-CH2-CHO.

Q: Which substituent activates a benzene ring the most for electrophilic aromatic substitution? -F - Me…

A: The Electron donating substituents are electron rich groups which activates the benzene ring for an…

Q: Provide mechanism with curved arrows for Part C: Synthesis of tetraphenylcyclopentadienone

Q: Explain why aprotic conditions favor a kinetic enolate ?

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: Devise a synthetic strategy to complete the following transformation. HO

A: Here we have to synthesize the following componund by retrosynthesis analysis and then by forward…

Q: Which position is activated toward electrophilic aromatic substitution? C O A O D OE B.

A: Option 2nd (D) will be correct.

Q: Why is methanol chosen as the solvent for recrystallization? What would happen if the student uses…

A: The above reaction is Electophilic substitution aromatic reaction. Which is known as Fridelcraft…

Q: A small base like KOtBu or LDA favors the Zaitsev product in an elimination reaction whereas a…

A: There is an empirical rule which determines the major and minor product . Saytzeff and Hoffmann…

Q: An alternative solvent to alkylate saccharin nucleophile could have been another OA. protic; ethanol…

A: Given statement is : An alternative solvent to alkylated saccharin nucleophile could have been…

Question

Please solve and explain?

14. Explain why pyrrole is an electron-rich heterocycle that is activated toward electrophilic aromatic
substitution, while pyridine is an electron poor heterocyclic that is deactivated toward electrophilic
aromatic substitution.

Expert Solution

This question has been solved!

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

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Selection Rules for Pericyclic Reactions

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

Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho and para positions rather than at meta.
What is the best way to remeber the differences between Sn1, Sn2, E1 and E2 reations?
most of the additions of bromine to double bonds gave entirely antistereochemistry. Explain why the addition to phenanthrene gives a mixture of synand anti stereochemistry
Provide mechanism with curved arrows for Part C: Synthesis of tetraphenylcyclopentadienone
p-Fluoronitrobenzene is more reactive toward hydroxide ion than is p-chloronitrobenzene. What does this tell you about the rate-determining step for nucleophilic aromatic substitution?
Please answer this NEATLY, COMPLETELY, and CORRECTLY for an UPVOTE. What is the purpose of deprotonation in the last step of electrophilic aromatic substitution? A) To neutralize the base that is present B) To make room for the electrophile C) To make the ring more reactive D) To restore an aromatic system E) None of the above
Which one would be most reactive toward electrophilic aromatic substitution?
Bromide Bhas normal activity (for a secondary bromide) towards SN1 substitution, but A has much higher reactivity and Chas much lower reactivity.
When naphthalene undergoes an irreversible electrophilic aromatic substitution, such as a Friedel–Crafts acylation, the major product is the kinetic product,which proceeds through the most stable arenium ion intermediate. InSection 23.7, we mentioned that substitution is generally favored at the αposition over the β position, which means that the arenium ion is more stable when the electrophile attaches to the α position. Explain this difference in arenium ion stabilities. Hint: Draw out allresonance structures for each arenium ion intermediate. Does each one have the same number of resonancestructures? How many resonance structures of each intermediate preserve the aromaticity?
Using resonance structures, explain why a nitroso group (– NO) is an ortho, para director that deactivates a benzene ring toward electrophilic attack.
Two of the following will give the same dimethylcyclooctatriene prod (A) while the third one will give the different dimethylcyclooctatriene (B) Preditc which of the ffg gives prod A or B
From 1 being the slowest and 4 being the fastest rank the aromatic hydrocarbons in terms of increasing raters of nitration via electrophilic aromatic substitution