Textbook Question
A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did she name correctly? Correct those that are misnamed.
a. 4-ethyl-2-pentyne
b. 1-bromo-4-heptyne
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Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis
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. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 31c
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 31cChapter 8, Problem 31c
A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did she name correctly? Correct those that are misnamed.
c. 2-methyl-3-hexyne d. 3-pentyne
Verified step by step guidance1
Step 1: Recall the IUPAC naming rules for alkynes. The parent chain must be the longest continuous chain containing the triple bond, and the chain is numbered to give the triple bond the lowest possible locant (position number). Substituents are named and numbered accordingly.
Step 2: Analyze compound c (2-methyl-3-hexyne). Identify the parent chain, which is a six-carbon chain (hex-). The triple bond is at position 3, and there is a methyl group at position 2. Verify if the numbering gives the triple bond the lowest possible locant. If not, renumber the chain and correct the name.
Step 3: Analyze compound d (3-pentyne). Identify the parent chain, which is a five-carbon chain (pent-). The triple bond is at position 3. Verify if the numbering gives the triple bond the lowest possible locant. If not, renumber the chain and correct the name.
Step 4: For both compounds, ensure that the substituents and triple bond positions are correctly named according to the IUPAC rules. If any errors are found, adjust the names accordingly.
Step 5: Compare the corrected names to the original names provided. Determine how many names were correct and list the corrected names for any misnamed compounds.
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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 for naming organic chemical compounds. It provides rules for naming based on the structure of the molecule, including the longest carbon chain, functional groups, and the position of substituents. Understanding these rules is essential for accurately naming compounds and identifying any errors in given names.
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The different parts of an IUPAC name
Alkynes
Alkynes are a class of hydrocarbons characterized by at least one carbon-carbon triple bond. They follow the general formula CnH2n-2 and are named based on the longest carbon chain containing the triple bond. Recognizing the structure and naming conventions for alkynes is crucial for determining the correctness of the provided names.
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Substituent Positioning
In organic nomenclature, the position of substituents on the main carbon chain is indicated by numbers. The lowest possible numbers are assigned to the substituents and functional groups to reflect their positions accurately. Misnaming can occur if the positions are incorrectly identified, making it important to verify these details when naming compounds.
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Related Practice
Textbook Question
Draw a condensed structure for each of the following:
k. cyclopentylacetylene
l. 5,6-dimethyl-2-heptyne
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Textbook Question
What is each compound's systematic name?
a.
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Textbook Question
Draw a condensed structure for each of the following:
i. diethylacetylene
j. di-tert-butylacetylene
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Textbook Question
What is each compound's systematic name?
b.
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Textbook Question
Identify the electrophile and the nucleophile in each of the following reaction steps. Then draw curved arrows to illustrate the bond-making and bond-breaking processes.
a.
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