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 30k,l
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 30k,lChapter 8, Problem 30k,l
Draw a condensed structure for each of the following:
k. cyclopentylacetylene
l. 5,6-dimethyl-2-heptyne
Verified step by step guidance1
Identify the structure of the parent compound for each molecule. For part (k), the parent compound is 'cyclopentylacetylene,' which consists of a cyclopentyl group (a five-membered ring) attached to an acetylene group (a triple bond between two carbon atoms). For part (l), the parent compound is '2-heptyne,' which is a seven-carbon chain with a triple bond starting at the second carbon.
For part (k), draw the cyclopentyl group as a five-membered ring. Then, attach a carbon atom to the ring, which will form the acetylene group. Add a triple bond between this carbon and the next carbon atom to complete the acetylene group.
For part (l), start by drawing the seven-carbon chain for heptyne. Place a triple bond between the second and third carbons to represent the '2-heptyne' structure.
For part (l), add the substituents. The name '5,6-dimethyl' indicates that there are methyl groups (-CH₃) attached to the fifth and sixth carbons of the heptyne chain. Add these methyl groups to the appropriate positions.
Write the condensed structure for each compound. For part (k), the condensed structure will show the cyclopentyl group attached to the acetylene group. For part (l), the condensed structure will show the seven-carbon chain with the triple bond and the methyl substituents at the correct positions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Condensed Structural Formula
A condensed structural formula is a way of representing a chemical compound that shows the arrangement of atoms and the connectivity between them without depicting all the bonds explicitly. It typically groups atoms together to indicate how they are connected, making it easier to visualize the structure of larger molecules. For example, in a condensed formula, carbon atoms in a chain may be written in sequence, with hydrogen atoms implied based on the tetravalency of carbon.
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How to interpret condensed structures.
Alkynes
Alkynes are a class of hydrocarbons characterized by at least one carbon-carbon triple bond. They follow the general formula CnH2n-2, where 'n' is the number of carbon atoms. Alkynes are unsaturated compounds, which means they contain fewer hydrogen atoms than alkanes and alkenes, leading to unique reactivity and properties. Understanding the structure and naming conventions of alkynes is essential for drawing their condensed structures accurately.
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Substituents in Organic Chemistry
Substituents are atoms or groups of atoms that replace hydrogen atoms in a hydrocarbon chain, influencing the compound's properties and reactivity. In the context of the given question, substituents like methyl groups (–CH3) can be attached to the main carbon chain, affecting the naming and structure of the compound. Recognizing how to identify and represent these substituents is crucial for accurately drawing condensed structures and understanding the overall molecular architecture.
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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
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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
Draw a condensed structure for each of the following:
g. 1-bromo-1-pentyne
h. 5-methyl-2-cyclohexenol
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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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Textbook Question
Draw a condensed structure for each of the following:
e. methoxyethyne
f. sec-butyl-tert-butylacetylene
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