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 17b
Bruice 8th EditionCh. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis SpectroscopyProblem 17bChapter 14, Problem 17b
Using curved arrows, show the principal fragments you would expect to see in the mass spectrum of each of the following compounds:
b. 
Verified step by step guidance1
Identify the compound provided in the problem. If the structure is not explicitly given, assume it is a common organic molecule. Understanding the structure is crucial for predicting fragmentation patterns.
Recall the basic principle of mass spectrometry: molecules are ionized (often by electron impact), and the resulting molecular ion (M⁺) can fragment into smaller ions. These fragments are detected and analyzed based on their mass-to-charge ratio (m/z).
Determine the most likely fragmentation sites in the molecule. Fragmentation typically occurs at weak bonds or bonds adjacent to functional groups. For example, bonds near carbonyl groups, alcohols, or halides are common sites for cleavage.
Use curved arrows to show the movement of electrons during the fragmentation process. For example, if a bond breaks heterolytically, one atom will take both electrons, forming a cation and a neutral fragment. If it breaks homolytically, two radicals are formed.
Draw the principal fragments resulting from the fragmentation process. Label the fragments with their respective m/z values if possible, and ensure the curved arrows clearly indicate the electron flow leading to each fragment.
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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 that may result from the breakdown of the original molecule.
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01:25
How to Read a Mass Spectrum
Curved Arrows in Mechanisms
Curved arrows are a notation used in organic chemistry to represent the movement of electrons during chemical reactions. They indicate the direction of electron flow, helping to visualize how bonds are formed or broken. Understanding how to use curved arrows is essential for predicting the products of reactions and the fragmentation patterns observed in mass spectrometry.
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04:32General Mechanism
Fragmentation Patterns
Fragmentation patterns refer to the specific ways in which a molecule breaks apart during mass spectrometry. These patterns are influenced by the structure of the molecule and the stability of the resulting fragments. Analyzing these patterns helps chemists deduce the structure of the original compound and identify the principal fragments that appear in the mass spectrum.
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08:06Common Splitting Patterns
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
Can a high-resolution mass spectrometer distinguish between them?
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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:
c.
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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
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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