Homework Help is Here – Start Your Trial Now!
Science
Chemistry
H3C-C=C-CH3 ^^C↔X ™ H₂C Alkynes are reduced to trans alkenes by a process called dissolving metal reduction. The reaction uses sodium or lithium metal as the reducing agent and liquid ammonia as the solvent. The method is specific in the formation of trans alkenes from alkynes. The method involves two successive transfers of single electrons from the alkali metal to the triple bond, with abstraction of protons from the ammonia solvent. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Na • Na, NH3 H3C-C=C-CH3 CH3 H3C CH3 Nat

H3C-C=C-CH3 ^^C↔X ™ H₂C Alkynes are reduced to trans alkenes by a process called dissolving metal reduction. The reaction uses sodium or lithium metal as the reducing agent and liquid ammonia as the solvent. The method is specific in the formation of trans alkenes from alkynes. The method involves two successive transfers of single electrons from the alkali metal to the triple bond, with abstraction of protons from the ammonia solvent. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Na • Na, NH3 H3C-C=C-CH3 CH3 H3C CH3 Nat

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
See similar textbooks
icon
Related questions
Question

Please answer both, and please help in indicating whether it is a single electron or a pair that is in movement, thank you!

 

**Alkyne Reduction to Trans Alkene: Dissolving Metal Reduction** **Chemical Reaction Overview:** - Reactants: An alkyne (H₃C-C≡C-CH₃) is treated with sodium (Na) and liquid ammonia (NH₃). - Product: A trans alkene (H₃C-CH=CH-CH₃) is formed. **Mechanism Explanation:** Alkynes can be reduced to trans alkenes using a process known as dissolving metal reduction. This reaction uses a metal, such as sodium or lithium, as the reducing agent and liquid ammonia as the solvent. The method is selective for forming trans alkenes from alkynes and involves two successive transfers of single electrons from the alkali metal to the triple bond, followed by the abstraction of protons from the ammonia solvent. **Electron Movement:** - The metal transfers a single electron to the triple bond, creating a radical anion intermediate. - This step is depicted by drawing curved arrows indicating the electron flow during the reaction. **Diagram Structure:** At the bottom: - Left: Sodium (Na) donates an electron to the alkyne (H₃C-C≡C-CH₃). - Right: The intermediate radical anion (H₃C-C·=C⁻-CH₃) and Na⁺. **Arrow-Pushing Instructions:** Includes visual tools for drawing reaction mechanisms, such as curved arrows showing electron movement. **Learning Points:** - Importance of stepwise electron transfer in dissolving metal reductions. - The role of metal and ammonia in achieving selective reduction to trans alkenes.
Transcribed Image Text:**Alkyne Reduction to Trans Alkene: Dissolving Metal Reduction** **Chemical Reaction Overview:** - Reactants: An alkyne (H₃C-C≡C-CH₃) is treated with sodium (Na) and liquid ammonia (NH₃). - Product: A trans alkene (H₃C-CH=CH-CH₃) is formed. **Mechanism Explanation:** Alkynes can be reduced to trans alkenes using a process known as dissolving metal reduction. This reaction uses a metal, such as sodium or lithium, as the reducing agent and liquid ammonia as the solvent. The method is selective for forming trans alkenes from alkynes and involves two successive transfers of single electrons from the alkali metal to the triple bond, followed by the abstraction of protons from the ammonia solvent. **Electron Movement:** - The metal transfers a single electron to the triple bond, creating a radical anion intermediate. - This step is depicted by drawing curved arrows indicating the electron flow during the reaction. **Diagram Structure:** At the bottom: - Left: Sodium (Na) donates an electron to the alkyne (H₃C-C≡C-CH₃). - Right: The intermediate radical anion (H₃C-C·=C⁻-CH₃) and Na⁺. **Arrow-Pushing Instructions:** Includes visual tools for drawing reaction mechanisms, such as curved arrows showing electron movement. **Learning Points:** - Importance of stepwise electron transfer in dissolving metal reductions. - The role of metal and ammonia in achieving selective reduction to trans alkenes.
### Title: Reduction of Alkynes to Trans Alkenes via Dissolving Metal Reduction **Reaction Overview:** The reaction illustrated involves the reduction of an alkyne, specifically 2-butyne (H₃C–C≡C–CH₃), to a trans alkene using dissolving metal reduction. Sodium (Na) and liquid ammonia (NH₃) are the reagents. **Mechanism Explanation:** 1. **Reaction Type:** - The process is known as dissolving metal reduction, utilizing sodium or lithium as the reducing agent and liquid ammonia as the solvent. 2. **Reaction Specificity:** - This method specifically converts alkynes to trans alkenes rather than cis alkenes or other products. 3. **Mechanism Steps:** - The reaction involves two successive transfers of single electrons. These electrons are transferred from the metal to the alkyne's triple bond. This is followed by the abstraction of protons from the ammonia solvent. 4. **Electron Movement:** - Curved arrows are used in chemical diagrams to indicate the movement of electrons during the reaction steps. **Instructions for Arrow Pushing:** - The image includes an "Arrow-pushing Instructions" button and icons, demonstrating how to draw these electron movement arrows in mechanisms. **Detailed Diagram Description:** 1. **Initial Reactants:** - The starting alkyne is shown on the left with a triple bond between the two central carbons (H₃C–C≡C–CH₃). 2. **Final Product:** - The right side of the reaction shows the final trans alkene product: H₃C–CH=CH–CH₃. 3. **Intermediate Steps:** - The diagram below the main reaction shows an intermediate with a single electron transfer creating a carbanion (H₃C–C•−–CH₃) and an amine (N:–H₂) in liquid ammonia. - The arrows in the mechanism detail how electrons are transferred and eventually lead to the abstraction of a proton, forming the final alkene and an amide ion (NH₂⁻). This detailed explanation assists students in understanding the step-by-step transformations and the importance of arrow pushing in visualizing electron flow in organic mechanisms.
Transcribed Image Text:### Title: Reduction of Alkynes to Trans Alkenes via Dissolving Metal Reduction **Reaction Overview:** The reaction illustrated involves the reduction of an alkyne, specifically 2-butyne (H₃C–C≡C–CH₃), to a trans alkene using dissolving metal reduction. Sodium (Na) and liquid ammonia (NH₃) are the reagents. **Mechanism Explanation:** 1. **Reaction Type:** - The process is known as dissolving metal reduction, utilizing sodium or lithium as the reducing agent and liquid ammonia as the solvent. 2. **Reaction Specificity:** - This method specifically converts alkynes to trans alkenes rather than cis alkenes or other products. 3. **Mechanism Steps:** - The reaction involves two successive transfers of single electrons. These electrons are transferred from the metal to the alkyne's triple bond. This is followed by the abstraction of protons from the ammonia solvent. 4. **Electron Movement:** - Curved arrows are used in chemical diagrams to indicate the movement of electrons during the reaction steps. **Instructions for Arrow Pushing:** - The image includes an "Arrow-pushing Instructions" button and icons, demonstrating how to draw these electron movement arrows in mechanisms. **Detailed Diagram Description:** 1. **Initial Reactants:** - The starting alkyne is shown on the left with a triple bond between the two central carbons (H₃C–C≡C–CH₃). 2. **Final Product:** - The right side of the reaction shows the final trans alkene product: H₃C–CH=CH–CH₃. 3. **Intermediate Steps:** - The diagram below the main reaction shows an intermediate with a single electron transfer creating a carbanion (H₃C–C•−–CH₃) and an amine (N:–H₂) in liquid ammonia. - The arrows in the mechanism detail how electrons are transferred and eventually lead to the abstraction of a proton, forming the final alkene and an amide ion (NH₂⁻). This detailed explanation assists students in understanding the step-by-step transformations and the importance of arrow pushing in visualizing electron flow in organic mechanisms.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
General Physical Properties of Organic Compounds
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY
SEE MORE TEXTBOOKS