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Ch. 24 - Benzene 2: Reactions Influenced by the Aromatic Ring
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Mullins 1st EditionCh. 24 - Benzene 2: Reactions Influenced by the Aromatic Ring문제 18a
23장, 문제 18a

Predict the product of the following substitution/addition reactions involving phenoxides.
(a) Chemical reaction diagram showing phenol and a chlorinated compound reacting with NaOH and water.

검증된 단계별 안내
1
Identify the reactants: The first reactant is a chlorophenol, specifically 2-chlorophenol, and the second reactant is a chlorocyclopentane.
Recognize the role of NaOH: Sodium hydroxide (NaOH) is a strong base that can deprotonate the phenol group, forming a phenoxide ion.
Formation of phenoxide ion: The hydroxide ion (OH-) from NaOH will deprotonate the hydroxyl group (OH) of the phenol, resulting in the formation of a phenoxide ion (C6H4ClO-).
Nucleophilic substitution: The phenoxide ion, being a good nucleophile, will attack the electrophilic carbon in the chlorocyclopentane, displacing the chloride ion (Cl-) and forming an ether linkage.
Predict the product: The final product will be an ether, specifically a phenoxycyclopentane, where the phenoxide ion has replaced the chloride ion in the cyclopentane ring.

비슷한 문제에 대한 검증된 영상 답변:

이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.

주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Phenoxide Ion Formation

Phenoxide ions are formed when phenol reacts with a strong base like NaOH. The hydroxyl group (OH) in phenol loses a hydrogen ion (H+), resulting in a negatively charged oxygen atom. This ion is more nucleophilic than phenol itself, making it more reactive in substitution reactions, particularly with alkyl halides.
추천 영상:
가이드 코스
3:39
Metal Ion Catalysis Concept 1

Nucleophilic Substitution Reaction

Nucleophilic substitution is a fundamental reaction where a nucleophile replaces a leaving group in a molecule. In this reaction, the phenoxide ion acts as the nucleophile, attacking the electrophilic carbon in the chlorinated compound, displacing the chloride ion. This process is crucial for forming new carbon-oxygen bonds in organic synthesis.
추천 영상:
01:47
Nucleophiles and Electrophiles can react in Substitution Reactions.

Stereochemistry in Substitution Reactions

Stereochemistry plays a vital role in substitution reactions, especially when the substrate is a chiral molecule. The reaction can proceed via an SN1 or SN2 mechanism, affecting the stereochemical outcome. In this case, the reaction likely follows an SN2 mechanism, leading to an inversion of configuration at the chiral center where the chloride is replaced by the phenoxide group.
추천 영상:
가이드 코스
1:38
Polymer Stereochemistry Concept 1
관련 실천
교과서 질문

Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.

(a)

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교과서 질문

Predict the product when the dihydroxybenzene shown is treated with a single equivalent of both base and haloalkane.

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교과서 질문

(a) Based on Figure 24.23, explain why meta-dihydroxybenzene is not oxidized to meta-quinone.

(b) If a meta-quinone is not produced, what would you expect the product of the oxidation of meta-dihydroxybenzene to be?

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교과서 질문

In light of Figure 24.22, provide a mechanism by which para-dihydroxybenzene is oxidized to para-quinone.

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교과서 질문

Predict the product of the following substitution/addition reactions involving phenoxides. [Because this problem represents a review of current and previous material, section numbers have been provided for your reference.]

(d)

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교과서 질문

Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.

(b)

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