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 56d
Mullins 1st EditionCh. 17 - Carbonyl Addition Reactions: Aldehydes and KetonesProblem 56dChapter 16, Problem 56d
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
Verified step by step guidance1
Step 1: Identify the longest carbon chain that contains the highest priority functional group. In this case, the aldehyde group (-CHO) is the highest priority, and the longest chain containing it is a six-carbon chain.
Step 2: Number the carbon chain starting from the end nearest to the highest priority functional group, which is the aldehyde group. This means the aldehyde group should be at position 1.
Step 3: Identify and name any substituents on the main chain. Here, there is a methyl group attached to the second carbon.
Step 4: Determine the correct position and configuration of the double bond. The double bond is between carbon 2 and carbon 3, and it is in the E configuration, meaning the highest priority groups on each carbon are on opposite sides.
Step 5: Combine all the elements to form the correct IUPAC name. The name should reflect the position of the double bond, the configuration, the substituents, and the aldehyde group.
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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 standardized system for naming chemical compounds. It ensures that each compound has a unique and universally accepted name, based on its structure. Key elements include identifying the longest carbon chain, functional groups, and the position of substituents, ensuring clarity and consistency in chemical communication.
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The different parts of an IUPAC name
E/Z Isomerism
E/Z isomerism is a type of stereoisomerism found in alkenes, where the spatial arrangement of substituents around the double bond differs. 'E' (entgegen) indicates that the highest priority groups are on opposite sides, while 'Z' (zusammen) means they are on the same side. This is determined using the Cahn-Ingold-Prelog priority rules, crucial for accurate naming and understanding molecular geometry.
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Functional Groups in Aldehydes
Aldehydes are organic compounds characterized by the presence of a carbonyl group (C=O) bonded to a hydrogen atom. In nomenclature, the aldehyde group is typically given priority in numbering, and the suffix '-al' is used. Understanding the placement and naming of aldehyde groups is essential for correctly identifying and naming compounds with this functional group.
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Related Practice
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
The following molecules were named incorrectly according to IUPAC nomenclature. Give the correct name of these compounds.
(a) 3-oxo-5-methylhexan-2-ol
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Textbook Question
In lieu of quenching the product of Grignard addition to a carbonyl with acid, alkyl halides can be added directly to generate ether products. Predict the product and show the mechanism of this process.
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Textbook Question
Starting with formaldehyde and the alkyl halides shown as the only sources of carbon, provide a synthesis of the following alcohol.
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