Textbook Question
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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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 53
Bruice 8th EditionCh. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis SpectroscopyProblem 53Chapter 14, Problem 53
What hydrocarbons that contain a six-membered ring will have a molecular ion peak at m/z = 112?
Verified step by step guidance1
Step 1: Understand the problem. The molecular ion peak at m/z = 112 corresponds to the molecular weight of the hydrocarbon. This means the hydrocarbon has a molecular formula with a total molecular weight of 112 g/mol.
Step 2: Recall the general formula for hydrocarbons. For a six-membered ring, the structure is typically a cycloalkane or an aromatic compound. Cycloalkanes follow the formula CnH2n, while aromatic compounds like benzene derivatives follow the formula CnH(2n-6).
Step 3: Calculate the possible number of carbon atoms. Start by assuming the molecular formula is CnH2n for a cycloalkane. Use the molecular weight of carbon (12 g/mol) and hydrogen (1 g/mol) to determine the number of carbons and hydrogens that sum to 112 g/mol.
Step 4: Consider aromatic compounds. If the compound is aromatic, adjust the formula to CnH(2n-6) and repeat the calculation to find the number of carbons and hydrogens that satisfy the molecular weight of 112 g/mol.
Step 5: Verify the structure. Once the molecular formula is determined, ensure that the structure corresponds to a six-membered ring. For example, check if the compound could be cyclohexane, methylcyclopentane, or a benzene derivative with appropriate substituents.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrocarbons
Hydrocarbons are organic compounds composed solely of hydrogen and carbon atoms. They can be classified into aliphatic (open-chain) and aromatic (ring) structures. Understanding the types of hydrocarbons is essential for identifying their molecular formulas and predicting their behavior in mass spectrometry.
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Aromaticity of Hydrocarbons
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 compounds, allowing for the identification of molecular ions. The molecular ion peak at m/z = 112 indicates the presence of a specific molecular weight, which is crucial for determining the possible hydrocarbons.
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Cyclohexane Derivatives
Cyclohexane derivatives are hydrocarbons that contain a six-membered carbon ring. The molecular formula for cyclohexane is C6H12, and its derivatives can include various functional groups or substitutions. To find hydrocarbons with a molecular ion peak at m/z = 112, one must consider the structural variations of cyclohexane that maintain this molecular weight.
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Related Practice
Textbook Question
A compound gives a mass spectrum with essentially only three peaks at m/z = 77 (40%), 112 (100%), and 114 (33%). Identify the compound.
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Textbook Question
Rank the following compounds from highest wavenumber to lowest wavenumber for their C-O absorption band:
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Textbook Question
Norlutin and Enovid are ketones that suppress ovulation, so they have been used clinically as contraceptives. For which of these compounds would you expect the infrared carbonyl absorption (C=O stretch) to be at a higher frequency? Explain.
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Textbook Question
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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Textbook Question
A mass spectrum shows significant peaks at m/z = 87, 115, 140, and 143. Which of the following compounds is responsible for that mass spectrum?
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