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 35i
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
Verified step by step guidance1
Step 1: Begin with an ester containing no more than eight carbon atoms. For example, you can use ethyl hexanoate (CH3(CH2)4COOCH2CH3) as the starting material.
Step 2: Perform a hydrolysis reaction to convert the ester into the corresponding carboxylic acid and alcohol. Use aqueous acid (H2SO4) or base (NaOH) as the hydrolysis reagent. The reaction mechanism involves nucleophilic attack on the carbonyl carbon of the ester.
Step 3: Reduce the carboxylic acid obtained from the hydrolysis step to the corresponding alcohol. Use a reducing agent such as lithium aluminum hydride (LiAlH4) for this step. The reaction mechanism involves hydride transfer to the carbonyl group.
Step 4: Perform a Williamson ether synthesis to create the diol (HO-(CH2)8-OH). React the alcohol obtained in the previous step with an alkyl halide (e.g., 1-bromohexane) in the presence of a strong base like NaH or KOH. This reaction forms an ether bond between the two alcohol groups.
Step 5: Purify the final product (HO-(CH2)8-OH) using techniques such as distillation or recrystallization to ensure the compound is free of impurities.
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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 in a process called esterification. This reaction can be catalyzed by an acid and results in the formation of an ester and water. Understanding this process is crucial for synthesizing compounds starting from an ester, as it provides the foundational knowledge of how esters can be manipulated in organic reactions.
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Hydrolysis of Esters
Hydrolysis of esters is the process where an ester reacts with water to form an alcohol and a carboxylic acid. This reaction can be either acid-catalyzed or base-catalyzed, and it is essential for understanding how to break down esters into their constituent parts. This concept is particularly relevant when considering the transformation of an ester into other functional groups or compounds.
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Chain Length and Functional Groups
In organic chemistry, the length of the carbon chain and the presence of functional groups significantly influence the properties and reactivity of compounds. For the synthesis of HO-(CH2)8-OH, which is a long-chain alcohol, it is important to consider how the carbon chain length affects solubility, boiling point, and reactivity. This understanding aids in selecting appropriate reagents and conditions for the synthesis.
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Related Practice
Textbook Question
Show how you would accomplish the following syntheses using amides as intermediates. You may use any necessary reagents.
(a) benzoic acid → benzyldimethylamine
(b) pyrrolidine → N-ethylpyrrolidine
(c) cyclopentanecarboxylic acid → cyclopentanecarbonitrile
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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
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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.
(d) Ph2CHOH
(e) PhCH2OH
(f) PhCOOH
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Textbook Question
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(d)
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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
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