Textbook Question
What reagents would you use to convert methyl propanoate to the following compounds?
c. N-ethylpropanamide
d. propanoic acid
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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 54
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 54Chapter 16, Problem 54
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?
Verified step by step guidance1
Step 1: Analyze the molecular structures of methyl acetate and butanone. Methyl acetate is an ester with the formula CH3COOCH3, while butanone is a ketone with the formula CH3COCH2CH3. Both compounds contain polar functional groups, but their dipole moments depend on the distribution of electron density and molecular geometry.
Step 2: Compare the dipole moments of the two compounds. The ester group in methyl acetate has two oxygen atoms contributing to its polarity, while the ketone group in butanone has one oxygen atom. The dipole moment is influenced by the electronegativity of oxygen and the molecular geometry. Consider how the electron density is distributed in each molecule.
Step 3: Evaluate the boiling points of the two compounds. Boiling point is influenced by intermolecular forces such as hydrogen bonding, dipole-dipole interactions, and London dispersion forces. Butanone, being a ketone, has a slightly larger molecular size and more surface area for dispersion forces compared to methyl acetate, which may affect its boiling point.
Step 4: Consider the functional groups and molecular weights. Methyl acetate has a molecular weight of 74 g/mol, while butanone has a molecular weight of 72 g/mol. Despite the similar molecular weights, the functional groups and intermolecular forces play a significant role in determining boiling points.
Step 5: Summarize the findings. Methyl acetate is expected to have a greater dipole moment due to the ester group with two oxygen atoms. Butanone is likely to have a higher boiling point due to stronger dispersion forces and dipole-dipole interactions associated with its ketone group and larger molecular surface area.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Dipole Moment
The dipole moment is a measure of the separation of positive and negative charges in a molecule, indicating its polarity. It arises from differences in electronegativity between atoms, leading to uneven charge distribution. A higher dipole moment suggests a more polar molecule, which can influence solubility and boiling points.
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Boiling Point
The boiling point of a compound is the temperature at which its vapor pressure equals the external pressure, causing it to change from liquid to gas. Factors affecting boiling points include molecular weight, intermolecular forces (like hydrogen bonding and dipole-dipole interactions), and molecular structure. Generally, stronger intermolecular forces lead to higher boiling points.
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Intermolecular Forces
Intermolecular forces are the forces of attraction or repulsion between molecules, influencing physical properties such as boiling and melting points. Key types include hydrogen bonds, dipole-dipole interactions, and London dispersion forces. The strength and type of these forces depend on molecular structure and polarity, affecting how substances behave in different states.
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Related Practice
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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Textbook Question
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)
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Textbook Question
What compounds are obtained from the following hydrolysis reactions?
c.
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