Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds

Problem 35

Chapter 11, Problem 35

Draw all possible resonance contributors for the two carbocations in the preceding reaction. Use the resonance contributors to explain why 1-naphthol is the major product of the reaction.

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Identify the two carbocations formed in the reaction. These are intermediates that can delocalize their positive charge through resonance. Label them as carbocation A and carbocation B for clarity.

Draw the resonance structures for carbocation A. Start by identifying any π-electrons or lone pairs on adjacent atoms that can delocalize the positive charge. Use curved arrows to show the movement of electrons and draw all valid resonance contributors.

Repeat the process for carbocation B. Again, identify any π-electrons or lone pairs on adjacent atoms that can stabilize the positive charge through resonance. Use curved arrows to show electron movement and draw all valid resonance contributors.

Compare the resonance contributors of carbocation A and carbocation B. Evaluate the stability of each carbocation based on the number of resonance structures, the delocalization of the positive charge, and the involvement of aromatic systems (if applicable).

Explain why 1-naphthol is the major product. Use the stability of the carbocations and the resonance contributors to justify why the reaction proceeds through the pathway leading to 1-naphthol. Highlight the role of resonance stabilization in determining the major product.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Resonance Structures

Resonance structures are different Lewis structures for the same molecule that depict the delocalization of electrons. They help illustrate how electrons are distributed across a molecule, particularly in systems with conjugated double bonds or lone pairs. The actual structure of the molecule is a hybrid of these resonance forms, which contributes to its stability and reactivity.

Carbocation Stability

Carbocations are positively charged carbon species that can vary in stability based on their structure. Stability increases with the degree of substitution; tertiary carbocations are more stable than secondary or primary ones due to hyperconjugation and inductive effects. Understanding the stability of carbocations is crucial for predicting reaction pathways and product formation.

Nucleophilic Aromatic Substitution

Nucleophilic aromatic substitution is a reaction where a nucleophile replaces a leaving group on an aromatic ring. This process often involves the formation of a Meisenheimer complex, where the nucleophile adds to the ring, followed by the elimination of the leaving group. The presence of electron-withdrawing groups can enhance the reactivity of the aromatic compound, influencing the major product formed in the reaction.

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Related Practice

Textbook Question

Draw the mechanism for formation of the two addition products.

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Textbook Question

What stereoisomers are obtained from the reaction of the alkenes in [PROBLEM 10-32] with a peroxyacid followed by reaction with hydroxide ion?

a. trans-2-butene

b. cis-2-butene

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Textbook Question

How do the major products obtained from rearrangement of the following arene oxides differ?

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Textbook Question

What stereoisomers are obtained from the reaction of the alkenes in [PROBLEM 10-32] with a peroxyacid followed by reaction with hydroxide ion?

c. cis-2-pentene

d. trans-2-pentene

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Textbook Question

The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.

a. What would be the major product if the NIH shift occurs? (Hint: A C—H bond is easier to break than a C—D bond.)

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Textbook Question

The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.

b. What would be the major product if the carbocation forms phenol by losing H⁺ or D⁺, rather than by going through the NIH shift?

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