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Ch.5 Review
Finding stereogenic centers
• All you are looking for is 4 different groups
Determining Chirality
• Method 1: Internal line of symmetry
• Can only be used for rings
• Is there an internal line of symmetry
• Yes: achiral
• no: chiral
Determining Chirality
Determining Chirality
• Method 2: Mirror and flip
• Step 1: Draw a line on side of molecule
• Step 2: transcribe the molecule while flipping it over the y axis
• Step 3 turn the molecule by 180 degrees by the z axis
Practice
Determine chirality
S and R naming
• Step 1: look at atoms surrounding stereogenic
center and rank them according to atomic
number
• Step 2: If there is a tie from step 1, look at the
groups surrounding the atoms we just looked at.
Look for a difference in atomic mass.
• Repeat until we are done
• Rule: If the atoms are the same but they are
connected by pi bonds, each bond counts once
R and S naming continued
• Step 3: draw arrows from priority 1 to 2 and from
2 to 3
• If clockwise: R
• If counterclockwise S
• Step 4: If group 4 is in the front, switch the sign.
(S to R) (R to S)
R and S IUPAC naming
• If there is one stereogenic center
• (S)-rest of name
• If there are 2 or more stereogenic centers
• (1R,2S)-rest of name
Determining Relationships
• Step 1: Find the molecular formula
• Same: continue to next step
• Different: different molecules
• Step 2: Is connectivity the same?
• Yes: continue to next step
• No: constitutional isomers
Determining Relationships
• Step 3: Count the number of stereo genic centers
• O= identical molecules
• 1?
• Identical chiral center= identical molecules
• Different chiral center= enantiomer
Determining Relationships
• 2 chiral centers?
• All the same: identical
• One or more different: Diastereomer
• All different: enantiomer
• If 2 chiral centers are symmetric and opposite they are meso
compounds
Practice
Determine the
relationship of each
set of molecules
Types of stereoisomers
• Meso compounds
• Achiral
• Have an equal number of opposite signs
• Enantiomers are nonsuperimposable mirror images
• Diastereomers are not mirror images
Optical activity
• Dextrorotary (d)= += clockwise rotation
• Levoratory (l)= - = counterclockwise rotation
• Ee= enantiomeric excess= creates optical activity
• Achiral molecules and racemates are optically inactive
• Formula for ee
• Specific rotation formulas
• Observed rotation formula

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Chapter 5

  • 2. Finding stereogenic centers • All you are looking for is 4 different groups
  • 3. Determining Chirality • Method 1: Internal line of symmetry • Can only be used for rings • Is there an internal line of symmetry • Yes: achiral • no: chiral
  • 5. Determining Chirality • Method 2: Mirror and flip • Step 1: Draw a line on side of molecule • Step 2: transcribe the molecule while flipping it over the y axis • Step 3 turn the molecule by 180 degrees by the z axis
  • 7. S and R naming • Step 1: look at atoms surrounding stereogenic center and rank them according to atomic number • Step 2: If there is a tie from step 1, look at the groups surrounding the atoms we just looked at. Look for a difference in atomic mass. • Repeat until we are done • Rule: If the atoms are the same but they are connected by pi bonds, each bond counts once
  • 8. R and S naming continued • Step 3: draw arrows from priority 1 to 2 and from 2 to 3 • If clockwise: R • If counterclockwise S • Step 4: If group 4 is in the front, switch the sign. (S to R) (R to S)
  • 9. R and S IUPAC naming • If there is one stereogenic center • (S)-rest of name • If there are 2 or more stereogenic centers • (1R,2S)-rest of name
  • 10. Determining Relationships • Step 1: Find the molecular formula • Same: continue to next step • Different: different molecules • Step 2: Is connectivity the same? • Yes: continue to next step • No: constitutional isomers
  • 11. Determining Relationships • Step 3: Count the number of stereo genic centers • O= identical molecules • 1? • Identical chiral center= identical molecules • Different chiral center= enantiomer
  • 12. Determining Relationships • 2 chiral centers? • All the same: identical • One or more different: Diastereomer • All different: enantiomer • If 2 chiral centers are symmetric and opposite they are meso compounds
  • 13. Practice Determine the relationship of each set of molecules
  • 14. Types of stereoisomers • Meso compounds • Achiral • Have an equal number of opposite signs • Enantiomers are nonsuperimposable mirror images • Diastereomers are not mirror images
  • 15. Optical activity • Dextrorotary (d)= += clockwise rotation • Levoratory (l)= - = counterclockwise rotation • Ee= enantiomeric excess= creates optical activity • Achiral molecules and racemates are optically inactive • Formula for ee • Specific rotation formulas • Observed rotation formula