Draw the major organic product for each of the following hydrogenation reactions. Indicate which stereoisomer is formed if more than one is possible. Pd/C OH + excess H2 Lindlar's catalyst

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...
icon
Related questions
Question
**Title: Understanding Hydrogenation Reactions in Organic Chemistry**

**Objective:**
To draw the major organic product for each of the following hydrogenation reactions and indicate which stereoisomer is formed if more than one is possible.

**Chemical Reaction Details:**

*Reactant:*
A cyclohexene ring with an attached ethanol group and a terminal alkyne (triple bond).

*Reactions:*

1. **Using Pd/C (Palladium on Carbon) with Excess H₂:**
   - This reaction involves complete hydrogenation. Palladium on carbon functions as a catalyst that facilitates the addition of hydrogen to both pi bonds in the alkyne, reducing it to a single bond.

2. **Using Lindlar's Catalyst:**
   - Lindlar’s catalyst is used for partial hydrogenation. It selectively hydrogenates alkynes to cis-alkenes (syn addition) without further reducing the double bond.

**Diagrams:**

The image contains two blank grids where students are expected to draw the products of these reactions:

- The first grid is associated with the Pd/C and excess H₂ reaction, where students should illustrate the complete reduction to an alkane.
  
- The second grid corresponds to the Lindlar’s catalyst reaction, where students should depict the partial reduction resulting in a cis-alkene.

**Notes:**

- When using **Pd/C and excess H₂**, expect the alkyne's triple bond to be reduced to a single bond resulting in an alkane.
  
- With **Lindlar’s catalyst**, the partial reduction leads to a cis-alkene, demonstrating a syn addition where both hydrogen atoms are added to the same side of the carbon chain.

**Conclusion:**
Understanding the conditions and catalysts involved in hydrogenation reactions helps predict the structure and stereochemistry of the resulting organic products.
Transcribed Image Text:**Title: Understanding Hydrogenation Reactions in Organic Chemistry** **Objective:** To draw the major organic product for each of the following hydrogenation reactions and indicate which stereoisomer is formed if more than one is possible. **Chemical Reaction Details:** *Reactant:* A cyclohexene ring with an attached ethanol group and a terminal alkyne (triple bond). *Reactions:* 1. **Using Pd/C (Palladium on Carbon) with Excess H₂:** - This reaction involves complete hydrogenation. Palladium on carbon functions as a catalyst that facilitates the addition of hydrogen to both pi bonds in the alkyne, reducing it to a single bond. 2. **Using Lindlar's Catalyst:** - Lindlar’s catalyst is used for partial hydrogenation. It selectively hydrogenates alkynes to cis-alkenes (syn addition) without further reducing the double bond. **Diagrams:** The image contains two blank grids where students are expected to draw the products of these reactions: - The first grid is associated with the Pd/C and excess H₂ reaction, where students should illustrate the complete reduction to an alkane. - The second grid corresponds to the Lindlar’s catalyst reaction, where students should depict the partial reduction resulting in a cis-alkene. **Notes:** - When using **Pd/C and excess H₂**, expect the alkyne's triple bond to be reduced to a single bond resulting in an alkane. - With **Lindlar’s catalyst**, the partial reduction leads to a cis-alkene, demonstrating a syn addition where both hydrogen atoms are added to the same side of the carbon chain. **Conclusion:** Understanding the conditions and catalysts involved in hydrogenation reactions helps predict the structure and stereochemistry of the resulting organic products.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps

Blurred answer
Knowledge Booster
Organopalladium 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