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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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 69d
Sketch the following spectra that would be obtained for 2-chloroethanol:
d. The proton-coupled 13C NMR spectrum.
Verified step by step guidance1
Identify the structure of 2-chloroethanol (ClCH2CH2OH) and determine the number of unique carbon environments. In this molecule, there are two distinct carbon atoms: one bonded to the chlorine atom (C1) and the other bonded to the hydroxyl group (C2).
Understand that in a proton-coupled 13C NMR spectrum, each carbon signal is split into a multiplet based on the number of directly attached protons. The splitting follows the n+1 rule, where n is the number of protons attached to the carbon.
Analyze the splitting for C1 (the carbon bonded to chlorine). This carbon is directly attached to two protons, so its signal will appear as a triplet (n+1 = 2+1 = 3).
Analyze the splitting for C2 (the carbon bonded to the hydroxyl group). This carbon is directly attached to two protons as well, so its signal will also appear as a triplet (n+1 = 2+1 = 3).
Sketch the spectrum with two signals: one triplet for C1 and another triplet for C2. Ensure the chemical shifts reflect the deshielding effects, with C1 appearing downfield (higher ppm) due to the electronegative chlorine atom, and C2 appearing upfield (lower ppm) relative to C1.
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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 hydrogen (1H) and carbon (13C), to provide information about the number of atoms, their environment, and connectivity. In proton-coupled 13C NMR, the interactions between protons and carbon atoms are observed, revealing details about the molecular structure.
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General NMR Features
Chemical Shifts
Chemical shifts in NMR spectroscopy refer to the variation in resonance frequency of a nucleus due to its electronic environment. In 13C NMR, chemical shifts are measured in parts per million (ppm) and provide insights into the types of carbon atoms present in a molecule. For 2-chloroethanol, the chemical shifts will reflect the presence of the hydroxyl group and the chlorine atom, influencing the electronic environment of the carbon atoms.
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Multiplicity and Coupling Patterns
Multiplicity in NMR refers to the splitting of NMR signals due to spin-spin coupling between neighboring nuclei. In proton-coupled 13C NMR, the number of peaks observed for each carbon signal corresponds to the number of protons on adjacent carbons, following the n+1 rule (where n is the number of neighboring protons). For 2-chloroethanol, the coupling patterns will help identify the connectivity and arrangement of the carbon and hydrogen atoms in the molecule.
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Related Practice
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:
c. The 13C NMR spectrum.
1
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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.
1
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Textbook Question
Identify each of the following compounds from its molecular formula and its 1H NMR spectrum:
b. C6H12O
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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.