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 32a
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 32aChapter 8, Problem 32a
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. 
Verified step by step guidance1
Step 1: Analyze the reactants. The molecule H₃CC≡CH with the positively charged iodine (I⁺) is the electrophile because it has an electron-deficient iodine atom. The negatively charged iodide ion (I⁻) is the nucleophile because it has a lone pair of electrons and is electron-rich.
Step 2: Identify the interaction between the electrophile and nucleophile. The nucleophile (I⁻) will attack the electrophile (I⁺) to form a new bond.
Step 3: Draw the curved arrow to represent the bond-making process. The curved arrow should start from the lone pair of electrons on the nucleophile (I⁻) and point toward the positively charged iodine atom (I⁺) in the electrophile.
Step 4: Illustrate the bond-breaking process. The bond between the positively charged iodine atom (I⁺) and the carbon atom in the electrophile will break, transferring the electrons to the carbon atom. Draw a curved arrow starting from the bond and pointing toward the carbon atom.
Step 5: Confirm the product structure. The final product will show the iodine atom (I⁻) bonded to the carbon atom, and the triple bond remains intact. Ensure the lone pairs on iodine are correctly represented in the product structure.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophiles
Electrophiles are species that accept electron pairs from nucleophiles during chemical reactions. They are typically positively charged or neutral molecules with an electron-deficient atom, making them attractive to electron-rich species. In the provided reaction, the positively charged carbon in the alkene acts as the electrophile, seeking electrons to form new bonds.
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03:
Nucleophile or Electrophile
Nucleophiles
Nucleophiles are electron-rich species that donate an electron pair to electrophiles in a chemical reaction. They can be negatively charged ions or neutral molecules with lone pairs of electrons. In the reaction shown, the negatively charged species (likely a carbanion or similar) acts as the nucleophile, attacking the electrophilic carbon to form a new bond.
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08:27Nucleophilic Addition
Curved Arrows in Mechanisms
Curved arrows are used in organic chemistry to illustrate the movement of electron pairs during bond-making and bond-breaking processes. The tail of the arrow indicates the electron source (where the electrons are coming from), while the head points to the electron destination (where the electrons are going). In the reaction, curved arrows will show how the nucleophile donates electrons to the electrophile and how bonds are formed or broken.
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04:32General Mechanism
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
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
What is each compound's systematic name?
a.
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Textbook Question
What is each compound's systematic name?
b.
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Textbook Question
What is each compound's systematic name?
c.
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