Textbook Question
Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.
(c)
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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 57a,b
Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.
(a) hept-6-en-1-ol → ε-caprolactone
(b) methoxybenzene → p-methoxybenzamide
Verified step by step guidance1
For part (a): Convert hept-6-en-1-ol to ε-caprolactone. Step 1: Oxidize the primary alcohol group (-CH2OH) in hept-6-en-1-ol to a carboxylic acid (-COOH) using an oxidizing agent such as Jones reagent (CrO3/H2SO4) or PCC in water.
Step 2: Perform an intramolecular cyclization reaction to form the lactone ring. Use an acid catalyst (e.g., H2SO4 or p-TsOH) to promote the nucleophilic attack of the hydroxyl group on the carboxylic acid, forming ε-caprolactone.
For part (b): Convert methoxybenzene to p-methoxybenzamide. Step 1: Perform a nitration reaction on methoxybenzene using a mixture of concentrated HNO3 and H2SO4 to introduce a nitro group (-NO2) at the para position relative to the methoxy group (-OCH3).
Step 2: Reduce the nitro group (-NO2) to an amine group (-NH2) using a reducing agent such as Sn/HCl or Fe/HCl.
Step 3: Convert the amine group (-NH2) to an amide group (-CONH2) by reacting the para-methoxyaniline with an acylating agent such as acetic anhydride or by using ammonium carbonate and a carboxylic acid derivative.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Multistep Synthesis
Multistep synthesis involves a series of chemical reactions that transform a starting material into a desired product through intermediate compounds. Understanding the sequence of reactions, including the reagents and conditions required at each step, is crucial for successfully completing the synthesis. This concept emphasizes the importance of planning and predicting the outcomes of each reaction to achieve the final product efficiently.
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Multistep Synthesis
Functional Group Transformation
Functional group transformation refers to the process of converting one functional group into another during a chemical reaction. This is essential in organic synthesis as it allows chemists to modify the reactivity and properties of molecules. Recognizing how different functional groups can be interconverted, such as alcohols to esters or amines, is key to designing effective synthetic pathways.
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Reagents and Reaction Conditions
The choice of reagents and reaction conditions is critical in organic synthesis, as they dictate the course and efficiency of the reactions. Different reagents can facilitate specific transformations, while conditions such as temperature, pressure, and solvent can influence reaction rates and selectivity. A thorough understanding of these factors is necessary to optimize the synthesis and ensure the desired product is obtained.
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Related Practice
Textbook Question
Methyl p-nitrobenzoate has been found to undergo saponification faster than methyl benzoate.
(a) Consider the mechanism of saponification, and explain the reasons for this rate enhancement.
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Textbook Question
Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.
(d)
393
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Textbook Question
Grignard reagents add to carbonate esters as they add to other esters.
(c) Diethyl carbonate is a liquid reagent that is easy to handle. Also show how you might use diethyl carbonate instead of methyl isocyanate to make Sevin® insecticide.
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Textbook Question
One mole of acetyl chloride is added to a liter of triethylamine, resulting in a vigorous exothermic reaction. Once the reaction mixture has cooled, 1 mole of ethanol is added. Another vigorous exothermic reaction results. The mixture is analyzed and found to contain triethylamine, ethyl acetate, and triethylammonium chloride. Propose mechanisms for the two exothermic reactions.
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Textbook Question
Grignard reagents add to carbonate esters as they add to other esters.
(c) Diethyl carbonate is a liquid reagent that is easy to handle. In contrast, phosgene is a highly toxic and corrosive gas. Show how you might use diethyl carbonate instead of phosgene to make Lexan®.
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