Textbook Question
Predict the product of the following alkyne reductions.
(c)
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Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 26c
Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 26cChapter 9, Problem 26c
Suggest alkynes that might be used to make the following trans-alkenes.
(c) 
Verified step by step guidance1
Identify the trans-alkene product structure. A trans-alkene has two substituents on opposite sides of the double bond. Analyze the given trans-alkene to determine the carbon chain and substituents.
Recall that alkynes can be reduced to trans-alkenes using a dissolving metal reduction, such as sodium (Na) in liquid ammonia (NH₃). This reaction selectively produces trans-alkenes from alkynes.
Determine the alkyne precursor by adding a triple bond in place of the double bond in the trans-alkene. This involves identifying the two carbons involved in the double bond and converting it into a triple bond.
Ensure that the alkyne precursor has the correct number of carbons and substituents to match the trans-alkene product after reduction. Verify that the structure of the alkyne aligns with the desired trans-alkene.
Propose the alkyne(s) that could be used as starting materials. For example, if the trans-alkene has substituents on opposite sides, the corresponding alkyne should have the same substituents attached to the triple bond carbons.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkynes
Alkynes are hydrocarbons that contain at least one carbon-carbon triple bond. They are unsaturated compounds and are represented by the general formula CnH2n-2. Alkynes can undergo various reactions, including addition reactions, which are crucial for synthesizing other organic compounds, such as alkenes and alcohols.
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09:11
Alkyne Hydration
Trans-Alkenes
Trans-alkenes are a type of alkene where the substituents on either side of the double bond are positioned on opposite sides, leading to a more stable configuration due to reduced steric strain. The geometric isomerism in alkenes is significant in organic chemistry, as it affects the physical and chemical properties of the compounds.
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Elimination Reactions
Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double or triple bond. In the context of synthesizing trans-alkenes from alkynes, a common method is the partial hydrogenation of alkynes or the elimination of a leaving group from a precursor compound, which can yield the desired trans configuration.
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Related Practice
Textbook Question
Suggest alkynes that might be used to make the following trans-alkenes.
(a)
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Textbook Question
When sodium generates electrons in the presence of ammonia, these electrons persist in solution, giving the blue color. However, electrons do not persist when sodium is added to water. Why?
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Textbook Question
Suggest alkynes that might be used to make the following trans-alkenes.
(b)
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Textbook Question
The following deprotonation step occurs during the trans reduction of an alkyne. Calculate Keq for this reaction.
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Textbook Question
Sodium amide, the base we use to deprotonate terminal alkynes, is synthesized by reducing ammonia via a mechanism similar to the reduction of alkynes in Figure 10.21. Suggest a mechanism for this reaction.
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