Textbook Question
Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.
(a) N-ethylbenzamide → benzylethylamine
(b) ethyl benzoate → N-ethylbenzamide
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Ch. 21 - Carboxylic Acid Derivatives
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- 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
Chapter 21, Problem 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
Verified step by step guidance1
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.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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.
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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.
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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.
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Related Practice
Textbook Question
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(c)
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Textbook Question
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
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Textbook Question
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
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Textbook Question
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(d)
762
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Textbook Question
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