Textbook Question
a. Which compound would you expect to have a greater dipole moment, methyl acetate or butanone?
b. Which would you expect to have a higher boiling point?
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Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 57d
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 57dChapter 16, Problem 57d
Using an alcohol for one method and an alkyl halide for the other, show two ways to make each of the following esters:
d. methyl phenylethanoate (odor of honey)
Verified step by step guidance1
Step 1: Understand the structure of methyl phenylethanoate. It is an ester with the formula CH₃OCOCH₂C₆H₅. The ester functional group consists of a carbonyl group (C=O) bonded to an oxygen atom, which is further bonded to a methyl group (CH₃). The phenylethanoate portion contains a phenyl group (C₆H₅) attached to a two-carbon chain.
Step 2: Method 1 - Using an alcohol: To synthesize methyl phenylethanoate, start with phenylacetic acid (C₆H₅CH₂COOH) as the carboxylic acid. React phenylacetic acid with methanol (CH₃OH) in the presence of an acid catalyst, such as sulfuric acid (H₂SO₄). The acid catalyst promotes the esterification reaction, where the hydroxyl group (-OH) of the carboxylic acid is replaced by the methoxy group (-OCH₃) from methanol, forming the ester.
Step 3: Method 2 - Using an alkyl halide: Begin with phenylacetic acid (C₆H₅CH₂COOH) as the carboxylic acid. First, convert phenylacetic acid into its carboxylate salt by reacting it with a base, such as sodium hydroxide (NaOH), to form sodium phenylacetate (C₆H₅CH₂COO⁻Na⁺). Then, perform an SN2 reaction between sodium phenylacetate and methyl iodide (CH₃I). The methyl group from methyl iodide replaces the sodium ion, forming methyl phenylethanoate.
Step 4: Highlight the reaction conditions: For the esterification method using an alcohol, ensure the reaction is carried out under reflux to drive the equilibrium toward ester formation. For the alkyl halide method, ensure the reaction is performed in a polar aprotic solvent, such as acetone, to facilitate the SN2 mechanism.
Step 5: Summarize the two methods: The first method involves direct esterification of phenylacetic acid with methanol under acidic conditions. The second method involves converting phenylacetic acid to its carboxylate salt, followed by an SN2 reaction with methyl iodide. Both methods yield methyl phenylethanoate as the final product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Esterification
Esterification is a chemical reaction that forms an ester from an alcohol and a carboxylic acid. This process typically involves the removal of a water molecule (condensation reaction) and can be catalyzed by an acid. Understanding this reaction is crucial for synthesizing esters, such as methyl phenylethanoate, from the appropriate reactants.
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Reactions of Amino Acids: Esterification Concept 1
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of ester synthesis, alkyl halides can undergo nucleophilic substitution with alcohols to form esters. This concept is essential for understanding how to create esters using alkyl halides.
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Reactivity of Alcohols and Alkyl Halides
The reactivity of alcohols and alkyl halides is pivotal in ester formation. Alcohols can act as nucleophiles, while alkyl halides serve as electrophiles. The choice of specific alcohols and alkyl halides influences the efficiency and outcome of the esterification process, making it important to select the right reactants for synthesizing methyl phenylethanoate.
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Related Practice
Textbook Question
What products would you expect to obtain from the following reactions?
a. malonic acid + 2 acetyl chloride
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Textbook Question
What reagents would you use to convert methyl propanoate to the following compounds?
c. N-ethylpropanamide
d. propanoic acid
Textbook Question
Because bromocyclohexane is a secondary alkyl halide, both cyclohexanol and cyclohexene are formed when the alkyl halide reacts with hydroxide ion. Suggest a method to synthesize cyclohexanol from bromocyclohexane that forms little or no cyclohexene.
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Textbook Question
What compounds are obtained from the following hydrolysis reactions?
d.
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Textbook Question
What reagents would you use to convert methyl propanoate to the following compounds?
a. isopropyl propanoate
b. sodium propanoate
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