Textbook Question
Draw a condensed structure for each of the following:
k. cyclopentylacetylene
l. 5,6-dimethyl-2-heptyne
2
views
Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 31a,b
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 31a,bChapter 8, Problem 31a,b
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
Verified step by step guidance1
Step 1: Review the IUPAC naming rules for alkynes. Alkynes are hydrocarbons containing a triple bond, and the parent chain should be the longest continuous chain containing the triple bond. Number the chain starting from the end closest to the triple bond to give it the lowest possible locant.
Step 2: Analyze compound (a) '4-ethyl-2-pentyne'. The parent chain is 'pentyne', which suggests a five-carbon chain with a triple bond. Verify the numbering of the chain to ensure the triple bond has the lowest possible locant. Check the position of the ethyl substituent and confirm whether the name follows IUPAC rules.
Step 3: Analyze compound (b) '1-bromo-4-heptyne'. The parent chain is 'heptyne', which suggests a seven-carbon chain with a triple bond. Verify the numbering of the chain to ensure the triple bond has the lowest possible locant. Check the position of the bromine substituent and confirm whether the name follows IUPAC rules.
Step 4: Correct any misnamed compounds based on the analysis. For compound (a), if the numbering does not give the triple bond the lowest locant, adjust the name accordingly. For compound (b), ensure the numbering prioritizes the triple bond and correctly places the bromine substituent.
Step 5: Compare the corrected names to the original names provided by the student. Determine how many names were correct and provide the corrected names for any misnamed compounds.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
6mWas this helpful?
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.
Recommended video:
Guided course
03:43
The different parts of an IUPAC name
Alkynes
Alkynes are hydrocarbons that contain at least one carbon-carbon triple bond. They are characterized by the suffix '-yne' in their names, which indicates the presence of this triple bond. The position of the triple bond is indicated by a number, which is crucial for correct nomenclature, especially when multiple substituents are present.
Recommended video:
Guided course
09:11Alkyne Hydration
Substituent Positioning
In organic chemistry, the positioning of substituents on the main carbon chain is critical for correct naming. The lowest possible numbers are assigned to the substituents and functional groups to reflect their positions. Misnaming often occurs when the numbering of the carbon chain does not follow this principle, leading to incorrect systematic names.
Recommended video:
4:06Reactions at the Allylic Position Example 3
Related Practice
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.
c. 2-methyl-3-hexyne d. 3-pentyne
3
views
Textbook Question
What is each compound's systematic name?
a.
1
views
Textbook Question
Draw a condensed structure for each of the following:
i. diethylacetylene
j. di-tert-butylacetylene
1
views
Textbook Question
Draw a condensed structure for each of the following:
g. 1-bromo-1-pentyne
h. 5-methyl-2-cyclohexenol
2
views
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.
1
views