Textbook Question
Two widely used pain relievers are aspirin and acetaminophen. Show how you would synthesize these drugs from phenol.
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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 54b
Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(b) 3-ethylpentanoic acid → 3-ethylpentanenitrile
Verified step by step guidance1
Step 1: Begin by identifying the functional group transformation required. In this case, you need to convert a carboxylic acid (-COOH) group in 3-ethylpentanoic acid to a nitrile (-CN) group in 3-ethylpentanenitrile.
Step 2: Recognize that carboxylic acids can be converted to nitriles through an intermediate step involving the formation of an amide. First, react 3-ethylpentanoic acid with ammonia (NH₃) to form 3-ethylpentanamide. This reaction typically requires heating and may use a dehydrating agent.
Step 3: Once the amide is formed, dehydrate the amide to form the nitrile. This can be accomplished using a dehydrating agent such as phosphorus pentoxide (P₂O₅) or thionyl chloride (SOCl₂). The dehydration reaction removes water and converts the amide (-CONH₂) to the nitrile (-CN).
Step 4: Ensure proper reaction conditions, such as temperature and solvent, to optimize the yield of 3-ethylpentanenitrile. For example, the dehydration step may require heating under reflux.
Step 5: Verify the product by analyzing its structure using techniques such as infrared spectroscopy (IR) to confirm the presence of the nitrile group (sharp peak around 2200 cm⁻¹) and ensure the conversion is complete.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Functional Groups
Understanding functional groups is essential in organic chemistry as they determine the chemical reactivity and properties of molecules. In this synthesis, we are converting a carboxylic acid (3-ethylpentanoic acid) into a nitrile (3-ethylpentanenitrile), which involves recognizing the functional groups involved and their transformations.
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02:36
Identifying Functional Groups
Nucleophilic Substitution Reactions
Nucleophilic substitution reactions are key mechanisms in organic synthesis where a nucleophile replaces a leaving group in a molecule. In this case, converting the carboxylic acid to a nitrile may involve a nucleophilic substitution step, where a suitable reagent can facilitate the transformation by replacing the -OH group of the acid.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Reagents and Reaction Conditions
Different reagents and reaction conditions are crucial for achieving specific transformations in organic synthesis. For the conversion of 3-ethylpentanoic acid to 3-ethylpentanenitrile, one might use reagents like thionyl chloride (SOCl2) to convert the acid to an acid chloride, followed by reaction with a nitrile source, highlighting the importance of selecting appropriate reagents.
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Related Practice
Textbook Question
Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(d) ethyl acetate → 3-methylpentan-3-ol
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Textbook Question
Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(c) isobutylamine → N-isobutylformamide
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Textbook Question
Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(a) isopentyl alcohol → isopentyl acetate (banana oil)
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Textbook Question
Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(e) cyclohexylamine → N-cyclohexylacetamide
(f) bromocyclohexane → dicyclohexylmethanol
Textbook Question
An ether extraction of nutmeg gives large quantities of trimyristin, a waxy crystalline solid of melting point 57°C. The IR spectrum of trimyristin shows a very strong absorption at 1733 cm-1. Basic hydrolysis of trimyristin gives 1 equivalent of glycerol and 3 equivalents of myristic acid (tetradecanoic acid).
(a) Draw the structure of trimyristin.
(b) Predict the products formed when trimyristin is treated with lithium aluminum hydride, followed by aqueous hydrolysis of the aluminum salts.
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