Textbook Question
Draw the structure for each of the following:
h. cyclohexanecarbonyl chloride
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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 4
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 4Chapter 16, Problem 4
Which is longer, the carbon–oxygen single bond in a carboxylic acid or the carbon–oxygen bond in an alcohol? Why?
Verified step by step guidance1
Understand the nature of the bonds: A carbon–oxygen single bond in a carboxylic acid is part of a functional group that includes both a hydroxyl (-OH) group and a carbonyl (C=O) group. In contrast, the carbon–oxygen bond in an alcohol is simply a single bond between a carbon atom and a hydroxyl (-OH) group.
Consider resonance effects: In a carboxylic acid, the carbon–oxygen single bond is influenced by resonance. The lone pairs on the oxygen in the hydroxyl group can delocalize into the carbonyl group, creating partial double-bond character in the carbon–oxygen single bond. This partial double-bond character shortens the bond length compared to a pure single bond.
Analyze the bond in an alcohol: The carbon–oxygen bond in an alcohol does not experience resonance effects. It is a pure single bond, which is typically longer than a bond with partial double-bond character.
Compare bond lengths: Bonds with partial double-bond character, like the carbon–oxygen single bond in a carboxylic acid, are shorter than pure single bonds, such as the carbon–oxygen bond in an alcohol.
Conclude based on bond character: The carbon–oxygen bond in an alcohol is longer than the carbon–oxygen single bond in a carboxylic acid due to the resonance effects in the carboxylic acid that shorten the bond length.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Bond Length
Bond length refers to the distance between the nuclei of two bonded atoms. It is influenced by factors such as atomic size and the type of bond (single, double, or triple). Generally, single bonds are longer than double bonds, and larger atoms tend to form longer bonds due to increased distance between their nuclei.
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Single bonds, double bonds, and triple bonds.
Carboxylic Acids vs. Alcohols
Carboxylic acids contain a carbonyl group (C=O) and a hydroxyl group (–OH) attached to the same carbon atom, while alcohols only have a hydroxyl group attached to a carbon atom. The presence of the carbonyl group in carboxylic acids can affect the bond lengths due to resonance and the overall hybridization of the carbon atom involved.
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Hybridization
Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate bonding. In carboxylic acids, the carbon atom is typically sp² hybridized, leading to a different bond character compared to the sp³ hybridized carbon in alcohols. This difference in hybridization can influence the bond lengths of the carbon-oxygen bonds in these compounds.
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Related Practice
Textbook Question
What reagent should be used to carry out the following reaction?
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Textbook Question
Draw the structure for each of the following:
i. α-chlorovaleric acid
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Textbook Question
Draw the structure for each of the following:
g. ethyl 2-chloropentanoate
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Textbook Question
There are three carbon–oxygen bonds in methyl acetate.
a. What are their relative bond lengths?
b. What are the relative infrared (IR) stretching frequencies of these bonds?
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Textbook Question
Which is a correct statement?
A. The delocalization energy of an ester is about 18 kcal/mol, and the delocalization energy of an amide is about 10 kcal/mol.
B. The delocalization energy of an ester is about 10 kcal/mol, and the delocalization energy of an amide is about 18 kcal/mol.
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