Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives

Bruice8th EditionOrganic ChemistryISBN: 9780135213711당신이 사용하는 게 아니라요?교과서 변경

Bruice 8th Edition

Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives

문제 13a(2)

16장, 문제 13a(2)

Show how the following compounds can be prepared, using ethyne as one of the starting materials:
2. 1-phenyl-2-butyn-1-ol

검증된 단계별 안내

Step 1: Start with ethyne (C₂H₂) as the base molecule. Ethyne is a simple alkyne with a triple bond between two carbon atoms. The goal is to build the desired compound step by step by adding functional groups and extending the carbon chain.

Step 2: Perform a nucleophilic addition reaction to extend the carbon chain. React ethyne with an alkyl halide (e.g., ethyl bromide, CH₃CH₂Br) in the presence of a strong base like sodium amide (NaNH₂). This will result in the formation of 1-butyne (CH≡C-CH₂CH₃).

Step 3: Introduce the phenyl group to the molecule. Use a Friedel-Crafts alkylation reaction or a Grignard reaction to attach a phenyl group (C₆H₅) to the terminal carbon of 1-butyne. This will yield 1-phenyl-1-butyne (C₆H₅-C≡C-CH₂CH₃).

Step 4: Perform a hydroboration-oxidation reaction to convert the terminal alkyne into an alcohol group. Use reagents such as BH₃ (borane) followed by H₂O₂ (hydrogen peroxide) and NaOH (sodium hydroxide). This will produce 1-phenyl-2-butyn-1-ol (C₆H₅-C≡C-CH(OH)-CH₃).

Step 5: Verify the structure of the final product to ensure it matches the desired compound, 1-phenyl-2-butyn-1-ol. Confirm that the phenyl group is attached to the first carbon, the hydroxyl group is on the second carbon, and the triple bond is between the second and third carbons.

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이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.

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주요 개념

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

Ethyne as a Building Block

Ethyne, also known as acetylene, is a simple alkyne that serves as a versatile building block in organic synthesis. Its triple bond allows for various reactions, including addition reactions with electrophiles and nucleophiles, making it a key starting material for constructing more complex molecules.

Alkyne Reactions

Alkynes undergo a variety of reactions, including hydrohalogenation, hydration, and coupling reactions. Understanding these reactions is crucial for synthesizing compounds like 1-phenyl-2-butyn-1-ol, as they allow for the introduction of functional groups and the formation of carbon-carbon bonds necessary for building the desired structure.

Functional Group Interconversion

Functional group interconversion involves transforming one functional group into another, which is essential in organic synthesis. In the case of 1-phenyl-2-butyn-1-ol, converting an alkyne to an alcohol through hydration or other methods is a key step, highlighting the importance of understanding how to manipulate functional groups to achieve the target compound.

Show how the following compounds can be prepared, using ethyne as one of the starting materials:2. 1-phenyl-2-butyn-1-ol