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Rank the following compounds from highest wavenumber to lowest wavenumber for their C=O absorption band:
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Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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 SpectroscopyProblema 58a
Bruice 8th EditionCh. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis SpectroscopyProblema 58aCapitolo 13, Problema 58a
The mass spectrum for a compound with molecular weight of 102 is shown below. Its IR spectrum has a broad, strong absorption at 3600 cm–1 and a medium absorption at 1360 cm–1.
a. Identify the compound.
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Step 1: Analyze the molecular weight of the compound, which is given as 102. This indicates the molecular ion peak (M+) in the mass spectrum should be at m/z = 102.
Step 2: Examine the IR spectrum data. The broad, strong absorption at 3600 cm⁻¹ suggests the presence of an -OH group, characteristic of alcohols. The medium absorption at 1360 cm⁻¹ indicates possible C-H bending vibrations, often associated with methyl groups.
Step 3: Look at the mass spectrum provided. The molecular ion peak (M+) at m/z = 102 confirms the molecular weight. Fragmentation patterns, such as peaks at m/z = 45 and m/z = 70, suggest possible loss of functional groups or fragments like CH3 or CH2OH.
Step 4: Combine the IR and mass spectrum data. The presence of an -OH group (from IR) and fragmentation patterns (from mass spectrum) suggest the compound is likely an alcohol. The molecular formula could be C4H10O, which matches the molecular weight of 102.
Step 5: Based on the data, the compound is likely butanol (C4H10O), as it fits the molecular weight, IR absorption characteristics, and fragmentation patterns observed in the mass spectrum.
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Mass Spectrometry
Mass spectrometry is an analytical technique used to measure the mass-to-charge ratio of ions. It provides information about the molecular weight of a compound and its structural features. In the context of the question, the mass spectrum indicates a molecular ion peak corresponding to the molecular weight of 102, which helps in identifying the compound.
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01:25
How to Read a Mass Spectrum
Infrared (IR) Spectroscopy
Infrared spectroscopy is a technique that measures the absorption of infrared light by a compound, providing information about its functional groups. The broad absorption at 3600 cm–1 suggests the presence of an -OH group, while the medium absorption at 1360 cm–1 may indicate a C-H bending vibration, which is common in alkanes or aromatic compounds.
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16:04General Features of IR Spect
Functional Group Identification
Identifying functional groups is crucial in organic chemistry as they determine the chemical reactivity and properties of compounds. The combination of mass spectrometry and IR spectroscopy data allows for the deduction of possible structures for the compound with a molecular weight of 102, guiding the identification process.
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02:36Identifying Functional Groups
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The mass spectrum for a compound with molecular weight of 102 is shown below. Its IR spectrum has a broad, strong absorption at 3600 cm–1 and a medium absorption at 1360 cm–1.
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