Predict the product when the dihydroxybenzene shown is treated with a single equivalent of both base and haloalkane.
Ch. 24 - Benzene 2: Reactions Influenced by the Aromatic Ring

Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471당신이 사용하는 게 아니라요?교과서 변경
23장, 문제 16a
Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(a) 
검증된 단계별 안내1
Identify the ether linkage in the given structure. The ether linkage is between the oxygen atom and the two carbon-containing groups.
Determine the two parts of the ether: the aryl group (phenyl group) and the alkyl group. In this structure, the aryl group is the phenyl ring, and the alkyl group is the isopropyl group attached to the oxygen.
To synthesize this ether, you need a phenoxide ion and an alkyl halide. The phenoxide ion is derived from phenol, where the hydrogen of the hydroxyl group is replaced by a metal ion, typically sodium or potassium.
The alkyl halide should correspond to the alkyl group in the ether. In this case, the alkyl group is isopropyl, so the alkyl halide should be isopropyl bromide or isopropyl chloride.
The reaction to form the ether is a nucleophilic substitution reaction, where the phenoxide ion acts as the nucleophile and attacks the electrophilic carbon in the alkyl halide, displacing the halide ion and forming the ether bond.

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
A phenoxide ion is formed when a phenol loses a hydrogen ion (H+) from its hydroxyl group (-OH), resulting in a negatively charged oxygen atom. This ion is a strong nucleophile, making it highly reactive in nucleophilic substitution reactions. Understanding the stability and reactivity of phenoxide ions is crucial for predicting their behavior in ether synthesis.
추천 영상:
가이드 코스
Metal Ion Catalysis Concept 1
Alkyl Halide
An alkyl halide is a compound derived from an alkane by replacing one or more hydrogen atoms with halogen atoms (such as chlorine, bromine, or iodine). These compounds are important in organic synthesis as they can undergo nucleophilic substitution reactions, where the halogen is replaced by a nucleophile, such as a phenoxide ion, to form ethers.
추천 영상:
How to name alkyl halides
Williamson Ether Synthesis
Williamson ether synthesis is a method for producing ethers by reacting an alkoxide ion (derived from an alcohol) with a primary alkyl halide. This reaction is favored with primary halides to avoid elimination reactions. Understanding this mechanism is essential for selecting appropriate reactants to synthesize specific aryl alkyl ethers.
추천 영상:
The Mechanism of Williamson Ether Synthesis.
관련 실천
교과서 질문
1087
views
교과서 질문
Predict the product of the following substitution/addition reactions involving phenoxides.
(a)
853
views
교과서 질문
Fluoxetine hydrochloride (Prozac®) is a widely used antidepressant. How might you stereoselectively install the indicated ether functional group (ROR) in (R)-fluoxetine?
1212
views
교과서 질문
Though the nitro group is electron-withdrawing by resonance, when in the meta position, it doesn’t communicate by resonance with the phenoxide anion. And yet, the pKₐ value of m-nitrophenol is lowered from 10 (the pKₐ value of unsubstituted phenol) to 8.4. Explain this observation.
1078
views
교과서 질문
Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(b)
1010
views
교과서 질문
Which proton, Ha or Hb, would you expect to have the lower pKa value?
1072
views
