Stereochemistry & Chirality

⚗️ Stereochemistry Chirality

Part 1 of 7 — Chirality & Stereocenters

1. Chiral

non-superimposable on its mirror image

2. Stereocenter

carbon with 4 different substituents

3. Achiral

superimposable on its mirror image

4. Plane of symmetry → achiral molecule

Plane of symmetry → achiral molecule

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Key Concepts Summary

• Chiral: non-superimposable on its mirror image
• Stereocenter: carbon with 4 different substituents
• Achiral: superimposable on its mirror image
• Plane of symmetry → achiral molecule

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R/S Configuration

Part 2 of 7 — R/S Configuration

1. Cahn-Ingold-Prelog priority rules

atomic number

2. R configuration

clockwise (priority 1→2→3 with 4 pointing back)

3. S configuration

counterclockwise

4. Priority

higher atomic number = higher priority

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Key Concepts Summary

• Cahn-Ingold-Prelog priority rules: atomic number
• R configuration: clockwise (priority 1→2→3 with 4 pointing back)
• S configuration: counterclockwise
• Priority: higher atomic number = higher priority

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Optical Activity

Part 3 of 7 — Optical Activity

1. Optical activity

rotating plane-polarized light

2. Enantiomers rotate light equal amounts but opposite directions

Enantiomers rotate light equal amounts but opposite directions

3. (+) dextrorotatory (clockwise); (-) levorotatory (counterclockwise)

(+) dextrorotatory (clockwise); (-) levorotatory (counterclockwise)

4. Racemic mixture

equal R and S → no net rotation

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Key Concepts Summary

• Optical activity: rotating plane-polarized light
• Enantiomers rotate light equal amounts but opposite directions
• (+) dextrorotatory (clockwise); (-) levorotatory (counterclockwise)
• Racemic mixture: equal R and S → no net rotation

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Stereoisomer Types

Part 4 of 7 — Stereoisomer Types

1. Enantiomers

mirror images, not superimposable

2. Diastereomers

stereoisomers that are NOT mirror images

3. Meso compounds

contain stereocenters but have internal plane of symmetry

4. n stereocenters → max 2ⁿ stereoisomers

n stereocenters → max 2ⁿ stereoisomers

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Key Concepts Summary

• Enantiomers: mirror images, not superimposable
• Diastereomers: stereoisomers that are NOT mirror images
• Meso compounds: contain stereocenters but have internal plane of symmetry
• n stereocenters → max 2ⁿ stereoisomers

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Fischer Projections

Part 5 of 7 — Fischer Projections

1. Fischer projections

horizontal = coming toward you, vertical = going away

2. Used especially for sugars and amino acids

Used especially for sugars and amino acids

3. Rotating 90° inverts configuration

Rotating 90° inverts configuration

4. Switching two groups inverts R/S

Switching two groups inverts R/S

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Key Concepts Summary

• Fischer projections: horizontal = coming toward you, vertical = going away
• Used especially for sugars and amino acids
• Rotating 90° inverts configuration
• Switching two groups inverts R/S

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Problem-Solving Workshop

Part 6 of 7 — Problem-Solving Workshop

1. Assigning R/S configuration to stereocenters

Assigning R/S configuration to stereocenters

2. Identifying stereoisomer relationships

Identifying stereoisomer relationships

3. Determining optical activity

Determining optical activity

4. Drawing and interpreting Fischer projections

Drawing and interpreting Fischer projections

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Key Concepts Summary

• Assigning R/S configuration to stereocenters
• Identifying stereoisomer relationships
• Determining optical activity
• Drawing and interpreting Fischer projections

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Synthesis & Review

Part 7 of 7 — Synthesis & Review

1. Stereochemistry determines biological activity

Stereochemistry determines biological activity

2. Enantiomers can have very different biological effects

Enantiomers can have very different biological effects

3. Understanding 3D structure is crucial in drug design

Understanding 3D structure is crucial in drug design

4. Review

chirality, configuration, and stereoisomers

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Key Concepts Summary

• Stereochemistry determines biological activity
• Enantiomers can have very different biological effects
• Understanding 3D structure is crucial in drug design
• Review: chirality, configuration, and stereoisomers

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