Textbook Question
What reagents should be used to carry out the following syntheses?
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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 35a
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 35aChapter 8, Problem 35a
Draw the structures and give the common and systematic names for alkynes with molecular formula C7H12. Ignore stereosiomers. (Hint: There are 14.)
Verified step by step guidance1
Step 1: Understand the molecular formula C7H12. This formula corresponds to a hydrocarbon with seven carbon atoms and twelve hydrogen atoms. Since the formula indicates fewer hydrogens than a fully saturated alkane (C7H16), it suggests the presence of multiple bonds or rings. Specifically, the formula fits the general formula for alkynes (CnH2n-2), indicating the presence of one triple bond.
Step 2: Begin by constructing the parent chain of seven carbon atoms. The triple bond can be placed at various positions along the chain. For each position, ensure the structure adheres to the molecular formula and satisfies the rules of valency for carbon atoms.
Step 3: Consider branching. The molecular formula allows for isomers with shorter parent chains and substituents. For example, you can create structures with a six-carbon parent chain and a methyl group as a substituent. Place the triple bond at different positions along the parent chain to generate additional isomers.
Step 4: Assign systematic names to each structure using IUPAC nomenclature rules. Identify the longest continuous chain containing the triple bond, number the chain starting from the end nearest the triple bond, and name substituents accordingly. For example, a structure with a triple bond between carbons 2 and 3 in a seven-carbon chain would be named 2-heptyne.
Step 5: Provide common names where applicable. Some alkynes may have traditional names based on historical usage. For example, ethyne is the common name for acetylene. While most of the C7H12 alkynes will not have widely recognized common names, ensure you check for any exceptions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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. In the case of C7H12, the presence of a triple bond indicates that the compound is an alkyne, which influences its reactivity and physical properties compared to alkenes and alkanes.
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Nomenclature
Nomenclature in organic chemistry refers to the systematic method of naming chemical compounds. For alkynes, the IUPAC naming convention involves identifying the longest carbon chain containing the triple bond, using the suffix '-yne' to denote the presence of the triple bond. Additionally, the position of the triple bond is indicated by a number, ensuring clarity in the compound's structure.
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Structural Isomers
Structural isomers are compounds that have the same molecular formula but differ in the arrangement of atoms. For C7H12, there are multiple structural isomers possible due to variations in the position of the triple bond and the branching of the carbon chain. Understanding structural isomers is crucial for accurately drawing the structures and naming all 14 possible alkynes for the given molecular formula.
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Related Practice
Textbook Question
Draw the mechanism for the following reaction:
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Textbook Question
How can the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbons as the desired product?
b. CH3CH2CH2CH2OH
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Textbook Question
How many would there be if stereoisomers are included?
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Textbook Question
What reagents should be used to carry out the following syntheses?
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Textbook Question
What reagents should be used to carry out the following syntheses?
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