3. Identify the stereocenters in the compounds below and assign each stereocenter as Ror S. Include the Cahn-Ingold-Prelog priorities for each substituent in the chiral center. H F NH H, HN
3. Identify the stereocenters in the compounds below and assign each stereocenter as Ror S. Include the Cahn-Ingold-Prelog priorities for each substituent in the chiral center. H F NH H, HN
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...
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Transcribed Image Text:**Exercise 3: Identification of Stereocenters in Chemical Compounds**
**Objective:**
Identify the stereocenters in the given chemical structures and assign each stereocenter as R or S. Include the Cahn-Ingold-Prelog priorities for each substituent in the chiral center.
**Chemical Structures:**
1. **Compound 1:**
- This structure features a bicyclic framework with an amide linkage. There is a stereocenter where the bicyclic structure, carbonyl group, and nitrogen are bonded.
- **Components:**
- **Oxygen (Double-bonded)**: Part of a carbonyl group.
- **Benzene-like ring**: Fused aromatic structure.
- **Nitrogen (Amide link)**: Forms part of the bicyclic structure.
- **Consideration for R/S Assignment:**
- Identify and rank the substituents around the stereocenter using atomic number priority.
2. **Compound 2:**
- This structure contains a phenyl ring connected to a saturated carbon with fluorine, hydrogen, and a methylamine group.
- **Components:**
- **Fluorine (F)**: Highest atomic number, thus highest priority.
- **Hydrogen (H)**: Lowest priority.
- **Methylamine (NH/CH3)**: Attached to the stereocenter.
- **Phenyl Ring**: Priority determined by chain connectivity and atomic number.
- **Consideration for R/S Assignment:**
- Follow Cahn-Ingold-Prelog rules to determine the stereochemistry at the chiral center.
**Graphs/Diagrams Explanation:**
- In both diagrams, stereochemistry is represented by wedges and dashed lines, indicating bonds out of the plane and into the plane, respectively.
- The positioning of substituents determines the configuration of each stereocenter.
For educational purposes, each stereocenter needs to be analyzed separately to assign R or S configuration following the Cahn-Ingold-Prelog system, which involves:
- Assigning priorities to substituents based on atomic number.
- Rotating the molecule so that the lowest priority group points away.
- Observing the order of rest priorities to assign R (clockwise) or S (counterclockwise).
**Note:** Correct stereochemical assignments are crucial for understanding the distinctive 3D arrangements within these molecules, which
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