교과서 질문
Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.
(a) N-ethylbenzamide → benzylethylamine
(b) ethyl benzoate → N-ethylbenzamide
1315
views
Ch. 21 - Carboxylic Acid Derivatives
Wade9th EditionOrganic ChemistryISBN: 9780135213728
당신이 사용하는 게 아니라요?교과서 변경다른 교과서를 선택하세요
TOC.tableOfContents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
21장, 문제 35d,e,f
Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.
(d) Ph2CHOH
(e) PhCH2OH
(f) PhCOOH
검증된 단계별 안내1
Step 1: For compound (d) Ph2CHOH (diphenylmethanol), start with an ester containing no more than eight carbons, such as methyl benzoate (C6H5COOCH3). Perform a Grignard reaction by reacting methyl benzoate with phenylmagnesium bromide (PhMgBr) in an ether solvent. This will form a tertiary alcohol intermediate. Hydrolyze the intermediate with water to yield diphenylmethanol.
Step 2: For compound (e) PhCH2OH (benzyl alcohol), start with an ester such as methyl benzoate (C6H5COOCH3). Reduce the ester to the corresponding alcohol using a reducing agent like lithium aluminum hydride (LiAlH4) in an ether solvent. Follow this with an aqueous workup to obtain benzyl alcohol.
Step 3: For compound (f) PhCOOH (benzoic acid), start with an ester such as methyl benzoate (C6H5COOCH3). Perform hydrolysis of the ester using either acidic (H2SO4, H2O) or basic (NaOH, H2O) conditions. If basic hydrolysis is used, the reaction will yield the carboxylate salt, which can be acidified with a strong acid (e.g., HCl) to produce benzoic acid.
Step 4: Ensure that the starting ester contains no more than eight carbons. For all three compounds, methyl benzoate (C6H5COOCH3) is a suitable starting material as it meets this requirement and provides the necessary aromatic ring for the target compounds.
Step 5: Verify the reaction conditions and reagents for each step to ensure the desired transformations occur efficiently. For example, confirm that the Grignard reagent is prepared under anhydrous conditions, and that the reducing agent (LiAlH4) is handled carefully due to its reactivity with water.
비슷한 문제에 대한 검증된 영상 답변:
이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
2m주요 개념
질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.
Ester Synthesis
Ester synthesis typically involves the reaction of a carboxylic acid with an alcohol, resulting in the formation of an ester and water. This process, known as esterification, can be catalyzed by an acid to increase the reaction rate. Understanding the structure and reactivity of esters is crucial for synthesizing compounds that contain them as functional groups.
추천 영상:
가이드 코스
01:28
Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis Example 2
Reduction Reactions
Reduction reactions in organic chemistry involve the gain of electrons or hydrogen, often resulting in the conversion of carbonyl compounds to alcohols. For example, the reduction of an aldehyde or ketone can yield primary or secondary alcohols, respectively. Familiarity with reducing agents, such as lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4), is essential for synthesizing alcohols from carbonyl precursors.
추천 영상:
07:12Reductive Amination
Phenolic Compounds
Phenolic compounds are characterized by the presence of a hydroxyl group (-OH) attached to an aromatic ring. They can be synthesized from various precursors, including phenols and aromatic aldehydes. Understanding the reactivity of phenolic compounds is important for manipulating their structures and creating derivatives, such as alcohols or carboxylic acids, in organic synthesis.
추천 영상:
02:27Identify the most acidic phenol
관련 실천
교과서 질문
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(c)
899
views
교과서 질문
Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.
(a) Ph3C–OH
(b) (PhCH2)2CHOH
(c) PhCONHCH2CH3
1246
views
교과서 질문
Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.
(i) HO–(CH2)8–OH
769
views
교과서 질문
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(d)
762
views
교과서 질문
Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.
(c) pyrrolidine → N-acetylpyrrolidine
(d) γ-aminobutyric acid → pyrrolidine
1011
views