Textbook Question
Predict the product of the following alkyne reductions.
(c)
2
views
Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 26b
Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 26bChapter 9, Problem 26b
Suggest alkynes that might be used to make the following trans-alkenes.
(b) 
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 replacing the double bond in the trans-alkene with a triple bond. This involves identifying the corresponding alkyne structure that would yield the given trans-alkene upon reduction.
Ensure that the alkyne precursor is a terminal or internal alkyne, depending on the structure of the trans-alkene. For example, if the trans-alkene has substituents on both sides of the double bond, the alkyne should be an internal alkyne.
Verify the proposed alkyne by mentally performing the dissolving metal reduction and confirming that the product matches the given trans-alkene. This ensures the correctness of the suggested alkyne precursor.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4mWas this helpful?
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.
Recommended video:
Guided course
09:11
Alkyne Hydration
Trans-Alkenes
Trans-alkenes are a type of alkene where the substituents on the double bond are on opposite sides, leading to a more stable configuration due to reduced steric strain. The geometric isomerism in alkenes is significant in determining their physical and chemical properties, making it essential to understand how to synthesize them from alkynes.
Recommended video:
3:04Alkene Metathesis Example 2
Hydroboration-Oxidation
Hydroboration-oxidation is a two-step reaction process used to convert alkynes into alkenes. In the first step, an alkyl borane is formed, which adds across the triple bond, followed by oxidation with hydrogen peroxide to yield the corresponding alcohol. This method is particularly useful for synthesizing trans-alkenes due to its regioselectivity and stereochemistry.
Recommended video:
Guided course
06:38General properties of hydroboration-oxidation.
Related Practice
Textbook Question
Suggest alkynes that might be used to make the following trans-alkenes.
(a)
1
views
Textbook Question
Suggest alkynes that might be used to make the following trans-alkenes.
(c)
4
views
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?
1
views
Textbook Question
The following deprotonation step occurs during the trans reduction of an alkyne. Calculate Keq for this reaction.
3
views
Textbook Question
Predict the product of the following alkyne reductions.
(b)
3
views