Why the arenium ion formed when en electrophile attaches to the 1 position of 2-methylnaphthalene is more stable than the one formed when it attaches to the 3 position is to be explained. Concept introduction: Aromatic compounds undergo electrophilic aromatic substitution reactions that involve an arenium cation. An arenium cation is one in which a ring carbon adjacent to the one where the electrophile attaches bears a positive charge. If there are two (or more) possible arenium ions, the major product is determined by the stability of each arenium ion. The most stable arenium ion determines the major product, the position where the electrophile attaches. The stability of an arenium ion depends on the number of resonance forms it can have. If the alternative cations have the same number of resonance forms, the stability depends on the number of resonance structures in which the aromaticity is preserved. This applies to substrates containing two or more (conjugated) aromatic rings.

Question

Want to see the full answer?

Answer 1

Question

Chapter 23, Problem 23.63P

Interpretation Introduction

Interpretation:

Why the arenium ion formed when en electrophile attaches to the 1 position of 2-methylnaphthalene is more stable than the one formed when it attaches to the 3 position is to be explained.

Concept introduction:

Aromatic compounds undergo electrophilic aromatic substitution reactions that involve an arenium cation. An arenium cation is one in which a ring carbon adjacent to the one where the electrophile attaches bears a positive charge. If there are two (or more) possible arenium ions, the major product is determined by the stability of each arenium ion. The most stable arenium ion determines the major product, the position where the electrophile attaches.

The stability of an arenium ion depends on the number of resonance forms it can have. If the alternative cations have the same number of resonance forms, the stability depends on the number of resonance structures in which the aromaticity is preserved. This applies to substrates containing two or more (conjugated) aromatic rings.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

+ C8H16O2 (Fatty acid) + 11 02 → 8 CO2 a. Which of the above are the reactants? b. Which of the above are the products? H2o CO₂ c. Which reactant is the electron donor? Futty acid d. Which reactant is the electron acceptor? e. Which of the product is now reduced? f. Which of the products is now oxidized? 02 #20 102 8 H₂O g. Where was the carbon initially in this chemical reaction and where is it now that it is finished? 2 h. Where were the electrons initially in this chemical reaction and where is it now that it is finished?

→ Acetyl-CoA + 3NAD+ + 1FAD + 1ADP 2CO2 + CoA + 3NADH + 1FADH2 + 1ATP a. Which of the above are the reactants? b. Which of the above are the products? c. Which reactant is the electron donor? d. Which reactants are the electron acceptors? e. Which of the products are now reduced? f. Which product is now oxidized? g. Which process was used to produce the ATP? h. Where was the energy initially in this chemical reaction and where is it now that it is finished? i. Where was the carbon initially in this chemical reaction and where is it now that it is finished? j. Where were the electrons initially in this chemical reaction and where is it now that it is finished?

Rank each of the following substituted benzene molecules in order of which will react fastest (1) to slowest (4) by electrophilic aromatic substitution. OCH 3 (Choose one) OH (Choose one) Br (Choose one) Explanation Check NO2 (Choose one) © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | A