Textbook Question
The mass spectra of 1-methoxybutane, 2-methoxybutane, and 2-methoxy-2-methylpropane are shown below. Match each compound with its spectrum.
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Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis 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
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Bruice 8th EditionCh. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis SpectroscopyProblem 17c
Bruice 8th EditionCh. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis SpectroscopyProblem 17cChapter 14, Problem 17c
Using curved arrows, show the principal fragments you would expect to see in the mass spectrum of each of the following compounds:
c. 
Verified step by step guidance1
Identify the molecular structure of the compound provided in the problem. Analyze its functional groups, bonds, and overall connectivity to determine potential sites for fragmentation during mass spectrometry.
Recall that in mass spectrometry, fragmentation occurs when the molecule is ionized, typically by electron impact, leading to the formation of a molecular ion (M⁺). This ion can then break into smaller fragments. Use curved arrows to represent the movement of electrons during bond cleavage.
Determine the most likely fragmentation pathways by considering the stability of the resulting cations and radicals. For example, cleavage near functional groups such as alcohols, carbonyls, or alkyl groups often leads to stable carbocations or resonance-stabilized ions.
Draw the principal fragments formed during the fragmentation process. Use curved arrows to show the electron movement that leads to the bond breaking and the formation of the fragments. Label the fragments with their respective m/z (mass-to-charge) ratios if possible.
Review the fragments and ensure that the most stable and abundant ions are represented. These are the ions most likely to appear as peaks in the mass spectrum. Consider factors such as resonance stabilization, inductive effects, and hyperconjugation when predicting fragment stability.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Mass Spectrometry
Mass spectrometry is an analytical technique used to measure the mass-to-charge ratio of ions. It involves ionizing chemical species and sorting the ions based on their mass. The resulting mass spectrum provides information about the molecular weight and structure of the compounds, allowing chemists to identify fragments and deduce structural features.
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How to Read a Mass Spectrum
Fragmentation Patterns
Fragmentation patterns refer to the specific ways in which a molecule breaks apart during ionization in mass spectrometry. These patterns are influenced by the molecular structure and stability of the resulting fragments. Understanding common fragmentation pathways helps predict the principal fragments that will appear in the mass spectrum of a compound.
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Curved Arrows in Mechanisms
Curved arrows are used in organic chemistry to represent the movement of electrons during chemical reactions and mechanisms. They indicate the flow of electron density, showing how bonds are formed or broken. In the context of mass spectrometry, using curved arrows can help illustrate the fragmentation process and the formation of specific ion fragments from the parent molecule.
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Related Practice
Textbook Question
Primary alcohols have a strong peak at m/z = 31.
a. What fragment is responsible for this peak?
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Textbook Question
Using curved arrows, show the principal fragments you would expect to see in the mass spectrum of each of the following compounds:
b.
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Textbook Question
Using curved arrows, show the principal fragments you would expect to see in the mass spectrum of each of the following compounds:
f.
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Textbook Question
The reaction of (Z)-2-pentene with water and a trace of H2SO4 forms two products. Identify the products from their mass spectra.
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Textbook Question
Using curved arrows, show the principal fragments you would expect to see in the mass spectrum of each of the following compounds:
d.
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