Textbook Question
What is each compound's systematic name?
b.
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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 40h
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 40hChapter 8, Problem 40h
Answer Problem 39, parts a–h, using 2-butyne as the starting material instead of propyne.
h. H2/Lindlar catalyst
Verified step by step guidance1
Identify the starting material: The problem specifies 2-butyne as the starting material. This is an alkyne with the structure CH3-C≡C-CH3.
Understand the reagent: H2 with a Lindlar catalyst is used to selectively hydrogenate alkynes to cis-alkenes. The Lindlar catalyst prevents full hydrogenation to an alkane.
Predict the product: When 2-butyne (CH3-C≡C-CH3) reacts with H2/Lindlar catalyst, the triple bond (C≡C) is reduced to a double bond (C=C), and the resulting product is a cis-alkene. The two methyl groups (CH3) on either side of the triple bond will remain in the same relative positions.
Draw the structure of the product: The product will be cis-2-butene, with the structure CH3-CH=CH-CH3, where the two hydrogens added during the reaction are on the same side of the double bond.
Verify stereochemistry: Ensure that the product is the cis-isomer (Z configuration), as the Lindlar catalyst specifically produces the cis-alkene and not the trans-alkene.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkyne Reduction
Alkynes can be reduced to alkenes or alkanes through various catalytic processes. The reduction of 2-butyne specifically involves the addition of hydrogen (H2) across the triple bond, converting it into a double bond (alkene) or a single bond (alkane) depending on the catalyst used.
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Birch Reduction Mechanism
Lindlar Catalyst
The Lindlar catalyst is a poisoned palladium catalyst that selectively reduces alkynes to cis-alkenes without further reducing them to alkanes. This catalyst is crucial for controlling the degree of hydrogenation, allowing for the formation of specific isomers in organic synthesis.
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Stereochemistry of Alkenes
Stereochemistry refers to the spatial arrangement of atoms in molecules and is particularly important in alkenes, which can exist as cis or trans isomers. The use of the Lindlar catalyst in the reduction of 2-butyne will yield cis-2-butene, highlighting the importance of stereochemical considerations in organic reactions.
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Related Practice
Textbook Question
Answer Problem 39, parts a–h, using 2-butyne as the starting material instead of propyne.
e. aqueous H2SO4, HgSO4
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Textbook Question
What is each compound's systematic name?
e.
f.
1601
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Textbook Question
Answer Problem 39, parts a–h, using 2-butyne as the starting material instead of propyne.
g. excess H2, Pd/C
1380
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Textbook Question
What is each compound's systematic name?
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1579
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Textbook Question
Answer Problem 39, parts a–h, using 2-butyne as the starting material instead of propyne.
f. R2BH in THF followed by H2O2/HO− /H2O
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