Textbook Question
The following molecules were named incorrectly according to IUPAC nomenclature. Give the correct name of these compounds.
b. (R)-6-bromo-7-oxoheptan-2-one
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Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 17 - Carbonyl Addition Reactions: Aldehydes and KetonesProblem 56a
Mullins 1st EditionCh. 17 - Carbonyl Addition Reactions: Aldehydes and KetonesProblem 56aChapter 16, Problem 56a
The following molecules were named incorrectly according to IUPAC nomenclature. Give the correct name of these compounds.
(a) 3-oxo-5-methylhexan-2-ol
Verified step by step guidance1
Step 1: Identify the longest carbon chain in the molecule. The longest chain will determine the base name of the compound. In this case, the longest chain is hexane, which consists of six carbon atoms.
Step 2: Determine the correct numbering of the carbon atoms in the chain. Number the chain from the end nearest to the highest priority functional group. Here, the hydroxyl group (-OH) has higher priority than the ketone group (oxo), so start numbering from the end closest to the hydroxyl group.
Step 3: Identify and name the substituents and functional groups. The molecule has a hydroxyl group (-OH) and a ketone group (oxo). The hydroxyl group is on the second carbon, and the ketone group is on the third carbon. Additionally, there is a methyl group on the fifth carbon.
Step 4: Assemble the name by placing the substituents and functional groups in alphabetical order, followed by the base name of the longest chain. The correct name should reflect the priority of the functional groups and the correct numbering of the chain.
Step 5: Ensure the name follows IUPAC rules, which prioritize the hydroxyl group over the ketone group. The correct name should be structured as: 2-hydroxy-5-methylhexan-3-one.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
IUPAC Nomenclature
IUPAC nomenclature is a systematic method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry. It provides a standardized way to name molecules so that chemists can easily communicate and understand the structure of a compound. The rules involve identifying the longest carbon chain, numbering the chain to give substituents the lowest possible numbers, and naming substituents and functional groups according to priority.
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03:43
The different parts of an IUPAC name
Functional Group Priority
In IUPAC nomenclature, functional groups are assigned a priority order which affects the numbering of the carbon chain and the suffix used in the compound's name. The group with the highest priority is given the lowest possible number and often dictates the suffix of the compound's name. For example, ketones have a higher priority than alcohols, so in a molecule containing both, the ketone group will influence the main chain numbering and suffix.
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02:36Identifying Functional Groups
Locants in Nomenclature
Locants are numbers used in chemical nomenclature to indicate the position of substituents, functional groups, or double/triple bonds on the main carbon chain. Correctly assigning locants is crucial for accurately naming a compound, as it ensures that the structure is unambiguously described. The goal is to assign the lowest possible numbers to the highest priority groups or substituents, following the IUPAC rules.
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Related Practice
Textbook Question
The following molecules were named incorrectly according to IUPAC nomenclature. Give the correct name of these compounds.
d. (E)-2-methylhex-2-en-6-al
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Textbook Question
Show the product expected by the Wolff–Kishner reduction of the following aldehydes/ketones.
(a)
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Textbook Question
During an oxidation reaction, there must also be a reduction. What is reduced in the Pinnick oxidation?
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Textbook Question
Draw the molecular orbital picture of but-3-en-2-one.
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Textbook Question
Which of the following cyclic hemiacetals would you expect to have the highest Keq for their formation? Explain your answer.
(a)
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