Textbook Question
Write structural formulas for the following compounds (includes both old- and new-style names).
(j) vinylacetylene
(k) (S)-3-methyl-1-penten-4-yne
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Ch.9 - Alkynes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 9, Problem 28a,b,c
Give IUPAC names for the following compounds.
(a) 
(b) 
(c) 
Verified step by step guidance1
Step 1: Identify the longest carbon chain in each compound that contains the highest priority functional group. For compound (a), the longest chain includes the alkyne group. For compound (b), the longest chain includes both the alkene and alkyne groups. For compound (c), the longest chain includes the alkyne group.
Step 2: Number the carbon atoms in the chain starting from the end nearest to the highest priority functional group. For compound (a), start numbering from the end closest to the alkyne. For compound (b), start numbering from the end closest to the alkene. For compound (c), start numbering from the end closest to the alkyne.
Step 3: Identify and name any substituents attached to the main chain. In compound (a), there is a phenyl group attached. In compound (b), there are methyl groups attached. In compound (c), there are methyl groups attached.
Step 4: Combine the names of the substituents with the name of the main chain, using the appropriate locants to indicate the position of each substituent and functional group. Ensure that the functional groups are indicated with their respective suffixes, such as '-yne' for alkynes and '-ene' for alkenes.
Step 5: Assemble the full IUPAC name by placing the substituents in alphabetical order, followed by the main chain name, ensuring that the locants are correctly placed to indicate the position of each group. Double-check the numbering to ensure the lowest possible numbers are used for the functional groups.
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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 identifying the structure of a compound based on its molecular formula and functional groups. Understanding the hierarchy of functional groups, the longest carbon chain, and the correct use of prefixes and suffixes is essential for accurately naming compounds.
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03:43
The different parts of an IUPAC name
Alkynes
Alkynes are hydrocarbons that contain at least one carbon-carbon triple bond. They are unsaturated compounds and are characterized by the general formula CnH2n-2. Recognizing the presence of a triple bond is crucial for determining the compound's name and its reactivity, as alkynes exhibit different chemical properties compared to alkanes and alkenes.
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09:11Alkyne Hydration
Substituents and Functional Groups
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 IUPAC naming, identifying and naming substituents, such as phenyl (Ph) groups, is essential for constructing the full name of the compound. Properly recognizing and placing substituents in the name is key to accurately conveying the compound's structure.
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Related Practice
Textbook Question
Give common names for the following compounds.
(a) CH3–C≡C–CH2CH3
(b) Ph–C≡C–H
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Textbook Question
Using hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)
d. hex-2-yne
e. hexan-2-one
f. hexanal
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Textbook Question
Give common names for the following compounds.
(c) 3-methyloct-4-yne
(d) (CH3)3C–C≡C–CH(CH3)CH2CH3
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Textbook Question
Using hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)
a. 1,2-dibromohexane
b. hex-1-yne
c. 2,2-dibromohexane
Textbook Question
Give IUPAC names for the following compounds.
(d)
(e)
(f)
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