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 69e
Sketch the following spectra that would be obtained for 2-chloroethanol:
e. The four parts of a DEPT 13C NMR spectrum.
Verified step by step guidance1
Understand the DEPT 13C NMR technique: DEPT (Distortionless Enhancement by Polarization Transfer) is used to differentiate between CH3, CH2, CH, and quaternary carbons in a molecule. It involves four spectra: DEPT-45, DEPT-90, DEPT-135, and a broadband decoupled spectrum showing all carbons.
Analyze the structure of 2-chloroethanol: The molecule contains two carbons. One is a CH2 group bonded to chlorine, and the other is a CH2 group bonded to hydroxyl (-OH). There are no CH or CH3 groups in this molecule.
Interpret the DEPT spectra: In DEPT-45, all carbons with attached hydrogens (CH, CH2, CH3) appear as positive peaks. In DEPT-90, only CH carbons appear. In DEPT-135, CH and CH3 carbons appear as positive peaks, while CH2 carbons appear as negative peaks. The broadband decoupled spectrum shows all carbons, including quaternary carbons.
Sketch the DEPT spectra for 2-chloroethanol: Since the molecule contains only CH2 carbons, the DEPT-45 spectrum will show two positive peaks, the DEPT-90 spectrum will show no peaks, the DEPT-135 spectrum will show two negative peaks, and the broadband decoupled spectrum will show two positive peaks.
Compare the provided images (A, B, C, D) with the expected DEPT spectra for 2-chloroethanol: Identify the image that matches the description above, where CH2 peaks are positive in DEPT-45, negative in DEPT-135, and present in the broadband decoupled spectrum, while no peaks appear in DEPT-90.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
DEPT NMR Spectroscopy
DEPT (Distortionless Enhancement by Polarization Transfer) NMR is a technique used to differentiate between carbon types in a molecule. It provides information about the number of hydrogen atoms attached to each carbon atom, allowing for the identification of CH3, CH2, and CH groups. This is crucial for interpreting the structure of organic compounds like 2-chloroethanol.
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General NMR Features
Carbon Types in Organic Molecules
In organic chemistry, carbon atoms can be classified based on their bonding: CH3 (methyl), CH2 (methylene), and CH (methine). Each type has distinct NMR signals, which help in determining the molecular structure. Understanding these types is essential for accurately sketching the DEPT NMR spectrum for compounds such as 2-chloroethanol.
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02:17Identifying organic molecules
Interpreting NMR Spectra
Interpreting NMR spectra involves analyzing the peaks and their intensities to deduce the molecular structure. In DEPT spectra, the presence or absence of signals for different carbon types indicates how many hydrogen atoms are attached. This skill is vital for accurately sketching the DEPT spectrum for 2-chloroethanol and understanding its chemical environment.
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10:06General NMR Features
Related Practice
Textbook Question
Calculate the amount of energy (in calories) required to flip an 1H nucleus in an NMR spectrometer that operates at 300 MHz.
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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:
c. The 13C NMR spectrum.
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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
Identify each of the following compounds from its molecular formula and its 1H NMR spectrum:
b. C6H12O
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