Textbook Question
Identify each of the following compounds from its molecular formula and its IR and 1H NMR spectra.
d. C4H8O2
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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 61
An alkyl halide reacts with an alkoxide ion to form a compound whose 1H NMR spectrum is shown here. Identify the alkyl halide and the alkoxide ion. (Hint: See Section 9.15.)
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Verified step by step guidance1
Step 1: Analyze the 1H NMR spectrum provided. The spectrum shows three distinct signals: a singlet at approximately 1.2 ppm corresponding to 9 hydrogens, a doublet at approximately 1.0 ppm corresponding to 6 hydrogens, and a quartet at approximately 3.5 ppm corresponding to 2 hydrogens. Additionally, there is a small singlet at approximately 2.2 ppm corresponding to 1 hydrogen.
Step 2: Interpret the signal at 1.2 ppm (9 H, singlet). This is characteristic of a tert-butyl group ((CH3)3C), where the three methyl groups are equivalent and produce a singlet due to the lack of neighboring hydrogens.
Step 3: Interpret the signal at 1.0 ppm (6 H, doublet). This is indicative of two equivalent methyl groups adjacent to a single hydrogen atom, which causes splitting into a doublet. This suggests the presence of an ethyl group (-CH2CH3).
Step 4: Interpret the signal at 3.5 ppm (2 H, quartet). This is characteristic of a methylene group (-CH2-) adjacent to a methyl group (-CH3), which causes splitting into a quartet. This further supports the presence of an ethyl group.
Step 5: Combine the information to deduce the reactants. The tert-butyl group likely comes from the alkoxide ion (tert-butoxide, (CH3)3CO-), and the ethyl group likely comes from the alkyl halide (ethyl bromide, CH3CH2Br). The reaction between tert-butoxide and ethyl bromide forms tert-butyl ethyl ether ((CH3)3COCH2CH3), consistent with the NMR spectrum.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkyl Halides
Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (F, Cl, Br, I). They are important in organic synthesis and can undergo nucleophilic substitution reactions. Understanding the structure and reactivity of alkyl halides is crucial for predicting the products of reactions, such as those involving alkoxide ions.
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Alkoxide Ions
Alkoxide ions are negatively charged species formed by deprotonation of alcohols. They are strong nucleophiles and are commonly used in organic reactions, particularly in the formation of ethers and in nucleophilic substitutions. Recognizing the structure and reactivity of alkoxide ions is essential for determining the outcome of reactions with alkyl halides.
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1H NMR Spectroscopy
1H NMR (Proton Nuclear Magnetic Resonance) spectroscopy is a powerful analytical technique used to determine the structure of organic compounds. It provides information about the number of hydrogen atoms in different environments, as indicated by chemical shifts and integration of peaks. Analyzing the NMR spectrum helps identify the alkyl halide and alkoxide ion involved in the reaction by correlating peak patterns with molecular structures.
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Related Practice
Textbook Question
The 1H NMR spectra of three isomers with molecular formula C7H14O are shown here. Which isomer produces which spectrum?
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Textbook Question
Compound A, with molecular formula C4H9Cl, shows two signals in its 13C NMR spectrum. Compound B, an isomer of compound A, shows four signals, and in the proton-coupled mode, the signal farthest downfield is a doublet. Identify compounds A and B.
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Textbook Question
Would it be better to use 1H NMR or 13C NMR spectroscopy to distinguish 1-butene, cis-2-butene, and 2-methylpropene? Explain your answer.
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Textbook Question
Identify the compound with molecular formula C7H14O that gives the following proton-coupled 13C NMR spectrum:
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Textbook Question
Identify each of the following compounds from its molecular formula and its IR and 1H NMR spectra:
b. C6H12O2
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