Textbook Question
Sketch the following spectra that would be obtained for 2-chloroethanol:
d. The proton-coupled 13C NMR spectrum.
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Ch. 14 - NMR Spectroscopy
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
Chapter 15, Problem 69c
Sketch the following spectra that would be obtained for 2-chloroethanol:
c. The 13C NMR spectrum.
Verified step by step guidance1
Identify the structure of 2-chloroethanol (ClCH2CH2OH). It contains two carbon atoms: one bonded to a chlorine atom and the other bonded to a hydroxyl group. These two carbons are chemically non-equivalent, meaning they will produce distinct signals in the 13C NMR spectrum.
Determine the chemical environment of each carbon atom. The carbon bonded to the chlorine atom (ClCH2-) is deshielded due to the electronegativity of chlorine, resulting in a downfield shift. The carbon bonded to the hydroxyl group (-CH2OH) is also deshielded, but to a lesser extent than the chlorine-bonded carbon.
Predict the approximate chemical shift range for each carbon. The carbon bonded to chlorine typically appears in the range of 40-80 ppm, while the carbon bonded to the hydroxyl group typically appears in the range of 50-70 ppm. These ranges are approximate and depend on the solvent and other experimental conditions.
Consider the splitting pattern. In 13C NMR, splitting due to coupling with directly bonded hydrogens (1H) is often not observed because broadband decoupling is typically used. Therefore, each carbon will appear as a single peak.
Sketch the spectrum. Represent the two distinct peaks on the x-axis (chemical shift in ppm) with their approximate positions based on the predicted ranges. Label the peak at the lower ppm value as the carbon bonded to the hydroxyl group (-CH2OH) and the peak at the higher ppm value as the carbon bonded to chlorine (ClCH2-).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nuclear Magnetic Resonance (NMR) Spectroscopy
NMR spectroscopy is a powerful analytical technique used to determine the structure of organic compounds. It exploits the magnetic properties of certain nuclei, such as carbon-13 (13C), to provide information about the number and environment of carbon atoms in a molecule. The resulting spectrum displays peaks corresponding to different carbon environments, allowing chemists to infer structural details.
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General NMR Features
Chemical Shifts in 13C NMR
Chemical shifts in 13C NMR refer to the variation in resonance frequency of carbon nuclei due to their electronic environment. Each unique carbon atom in a molecule will resonate at a different frequency, which is measured in parts per million (ppm). The position of these peaks on the spectrum provides insight into the types of functional groups and the overall structure of the compound.
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11:441H NMR Chemical Shifts
Integration and Peak Multiplicity
In 13C NMR, integration refers to the area under the peaks, which correlates with the number of equivalent carbon atoms contributing to that signal. Peak multiplicity, influenced by neighboring hydrogen atoms, indicates the number of adjacent protons and helps deduce the connectivity of the carbon atoms. Understanding these aspects is crucial for interpreting the spectrum of 2-chloroethanol accurately.
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Related Practice
Textbook Question
Sketch the following spectra that would be obtained for 2-chloroethanol:
a. The 1H NMR spectrum for an anhydrous sample of the alcohol.
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Textbook Question
How can 1H NMR be used to prove that the addition of HBr to propene follows the rule that says that the electrophile adds to the sp2 carbon bonded to the most hydrogens?
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Textbook Question
Sketch the following spectra that would be obtained for 2-chloroethanol:
b. The 1H NMR spectrum for a sample of the alcohol that contains a trace amount of acid.
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Textbook Question
Draw a splitting diagram for the Hb proton if Jbc = 10 and Jba = 5.
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Textbook Question
Sketch the following spectra that would be obtained for 2-chloroethanol:
e. The four parts of a DEPT 13C NMR spectrum.
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