Homework Help is Here – Start Your Trial Now!
Science
Chemistry
Using Cahn-Ingold-Prelog convention, assign R or S to each chiral center in the following compound. CH3 H3C 2 Br Carbon 1 = R Carbon 2 = R Carbon 1 = s Carbon 2 = s Carbon 1 = R Carbon 2 = S Carbon 1 = S Carbon 2 = R CH3

Using Cahn-Ingold-Prelog convention, assign R or S to each chiral center in the following compound. CH3 H3C 2 Br Carbon 1 = R Carbon 2 = R Carbon 1 = s Carbon 2 = s Carbon 1 = R Carbon 2 = S Carbon 1 = S Carbon 2 = R CH3

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
### Using Cahn-Ingold-Prelog Convention to Assign R or S to Chiral Centers In this exercise, we will apply the Cahn-Ingold-Prelog convention to assign the R or S configuration to each chiral center in the given compound. #### Chemical Structure The compound depicted is: \[ \text{CH}_3-\text{CH}(\text{CH}_3)-\text{CH}(\text{Br})-\text{CH}_3 \] Below is a visual representation of the structure: ``` CH₃ | H₃C-C-CH₃ | Br ``` The chiral centers are labeled as Carbon 1 and Carbon 2. #### Possible Assignments To assign the correct stereochemistry (R or S) to each chiral center, select the correct combination from the following options: - ⃝ Carbon 1 = R; Carbon 2 = R - ⃝ Carbon 1 = S; Carbon 2 = S - ⃝ Carbon 1 = R; Carbon 2 = S - ⃝ Carbon 1 = S; Carbon 2 = R #### Steps to Determine Configuration 1. **Assign Priorities**: Assign priority numbers to the substituents attached to each chiral center based on atomic number. 2. **Orient the Molecule**: Orient the molecule so that the lowest priority group (4) is pointing away from you. 3. **Determine the Sequence**: Determine the sequence of the remaining groups (1, 2, 3). 4. **Assign Configuration**: - If the sequence 1-2-3 is clockwise, the configuration is R (rectus). - If the sequence is counterclockwise, the configuration is S (sinister). #### Select the Correct Answer Carefully follow the above steps for each chiral center to select the appropriate configuration from the options provided.
Transcribed Image Text:### Using Cahn-Ingold-Prelog Convention to Assign R or S to Chiral Centers In this exercise, we will apply the Cahn-Ingold-Prelog convention to assign the R or S configuration to each chiral center in the given compound. #### Chemical Structure The compound depicted is: \[ \text{CH}_3-\text{CH}(\text{CH}_3)-\text{CH}(\text{Br})-\text{CH}_3 \] Below is a visual representation of the structure: ``` CH₃ | H₃C-C-CH₃ | Br ``` The chiral centers are labeled as Carbon 1 and Carbon 2. #### Possible Assignments To assign the correct stereochemistry (R or S) to each chiral center, select the correct combination from the following options: - ⃝ Carbon 1 = R; Carbon 2 = R - ⃝ Carbon 1 = S; Carbon 2 = S - ⃝ Carbon 1 = R; Carbon 2 = S - ⃝ Carbon 1 = S; Carbon 2 = R #### Steps to Determine Configuration 1. **Assign Priorities**: Assign priority numbers to the substituents attached to each chiral center based on atomic number. 2. **Orient the Molecule**: Orient the molecule so that the lowest priority group (4) is pointing away from you. 3. **Determine the Sequence**: Determine the sequence of the remaining groups (1, 2, 3). 4. **Assign Configuration**: - If the sequence 1-2-3 is clockwise, the configuration is R (rectus). - If the sequence is counterclockwise, the configuration is S (sinister). #### Select the Correct Answer Carefully follow the above steps for each chiral center to select the appropriate configuration from the options provided.
### Assigning R or S Configuration Using Cahn-Ingold-Prelog Convention To determine the configuration of chiral centers in the compound shown, we will utilize the Cahn-Ingold-Prelog (CIP) priority rules. The compound provided has the following structure: #### Image Description: The image depicts a cyclohexane ring with a single chiral center on one of the carbon atoms. This chiral center is bonded to a methyl group (CH3), which is directed as a wedge (indicating the bond is coming out of the plane of the page). ### Steps to Assign R or S Configuration: 1. **Identify the Chiral Center:** The chiral center in this compound is the carbon atom that is bonded to four different groups: the cyclohexane ring itself, a hydrogen atom (not explicitly shown), a methyl group (CH3), and the rest of the ring. 2. **Assign Priorities to Substituents:** - First, assign priorities to the substituents attached to the chiral center based on atomic numbers: - **Highest Priority (1)**: The part of the cyclohexane ring extending clockwise from the chiral center. - **Second Highest Priority (2)**: The methyl group (CH3). - **Third Highest Priority (3)**: The hydrogen atom (not shown but inferred as the lowest priority by default). 3. **Orient the Molecule:** Examine the molecule so that the substituent with the lowest priority (hydrogen, in this case) is positioned directly away from you, behind the plane of the paper. 4. **Determine the Configuration:** Trace a path from the highest priority substituent (1) through the second (2) to the third (3). If the path you trace is clockwise, the configuration is R (rectus). If counterclockwise, the configuration is S (sinister). 5. **Assign R or S:** - **Clockwise Path:** R configuration - **Counterclockwise Path:** S configuration ### Example Conclusion: By carefully following the CIP rules and assessing the 3D configuration around the chiral center, you can determine whether each chiral center in the given compound is R or S. For this specific compound, use a molecular model or detailed scrutiny to carefully deduce the final configuration, as cyclohexane can be conformationally flexible, potentially influencing the
Transcribed Image Text:### Assigning R or S Configuration Using Cahn-Ingold-Prelog Convention To determine the configuration of chiral centers in the compound shown, we will utilize the Cahn-Ingold-Prelog (CIP) priority rules. The compound provided has the following structure: #### Image Description: The image depicts a cyclohexane ring with a single chiral center on one of the carbon atoms. This chiral center is bonded to a methyl group (CH3), which is directed as a wedge (indicating the bond is coming out of the plane of the page). ### Steps to Assign R or S Configuration: 1. **Identify the Chiral Center:** The chiral center in this compound is the carbon atom that is bonded to four different groups: the cyclohexane ring itself, a hydrogen atom (not explicitly shown), a methyl group (CH3), and the rest of the ring. 2. **Assign Priorities to Substituents:** - First, assign priorities to the substituents attached to the chiral center based on atomic numbers: - **Highest Priority (1)**: The part of the cyclohexane ring extending clockwise from the chiral center. - **Second Highest Priority (2)**: The methyl group (CH3). - **Third Highest Priority (3)**: The hydrogen atom (not shown but inferred as the lowest priority by default). 3. **Orient the Molecule:** Examine the molecule so that the substituent with the lowest priority (hydrogen, in this case) is positioned directly away from you, behind the plane of the paper. 4. **Determine the Configuration:** Trace a path from the highest priority substituent (1) through the second (2) to the third (3). If the path you trace is clockwise, the configuration is R (rectus). If counterclockwise, the configuration is S (sinister). 5. **Assign R or S:** - **Clockwise Path:** R configuration - **Counterclockwise Path:** S configuration ### Example Conclusion: By carefully following the CIP rules and assessing the 3D configuration around the chiral center, you can determine whether each chiral center in the given compound is R or S. For this specific compound, use a molecular model or detailed scrutiny to carefully deduce the final configuration, as cyclohexane can be conformationally flexible, potentially influencing the
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 1 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Isomerism in 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.
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