1. E XPERIMENT 9 Stereochemistry: Enantiomers and Diastereomers

2. This experiment is NOT in the current edition of the lab manual. Each student should print a copy of the FINAL LAB REPORT sheet accessible on the Blackboard Learn course website and bring it to lab to complete. Molecular model kits will be provided for assistance, or students can bring their own to lab. There is no other PRE lab or POST lab assignment for this experiment, just the completion of the FINAL LAB REPORT sheet. T HE LAB REPORT …

3. Fill in the blanks using a single term from the list at the top. Use textbook for assistance if necessary.

4. L OCATING C HIRALITY C ENTERS Ignore sp 2 and sp hybridized centers. Ignore CH 2 and CH 3 groups. Identify any carbon atoms bearing 4 different groups. Identify the chirality centers in each of the following compounds. Mark each chirality center with a asterisk (*):

5. T HE LAB REPORT … Read the SKILL BUILDER section. Follow instructions given.

6. A SSIGNING P RIORITY AND ABSOLUTE CONFIGURATION Step 1: Identify the four atoms directly attached to the chirality center. Step 2: Assign a priority to each atom based on its atomic number. The highest atomic number =1, the lowest = 4. Step 3: If two atoms have the same atomic number, move away from the chirality center looking for the first point of difference. 14 OOOOOO CHHCHH Higher = 2 Lower =3

7. A SSIGNING P RIORITY AND ABSOLUTE CONFIGURATION Step 4: Redraw the chirality center showing only priorities. Step 5: Rotate the molecule so that the 4 th priority atom is on a dash. Step 5: Determine whether the sequence 1-2-3 follows a clockwise order (R) or a counterclockwise order (S).

8. T HE LAB REPORT … Follow instructions given for all problems.

9. T HE LAB REPORT … Read the SKILL BUILDER section. Follow instructions given. Show all calculations, not just the value!

10. T HE LAB REPORT … Read the SKILL BUILDER section. Follow instructions given. Molecular models will be provided, or you can bring your own with you to lab!

11. D ETERMINING STEREOISOMERIC RELATIONSHIP Step 1: Compare the configuration at each chirality center. These two chirality centers have opposite configuration… Step 2: If only SOME of the chirality centers have opposite configuration, the compounds are DIASTEREOMERS. These two chirality centers have SAME configuration…

12. T HE LAB REPORT … Read the SKILL BUILDER section. Follow instructions given. Molecular models will be provided, or you can bring your own with you to lab!

13. I DENTIFYING MESO COMPOUNDS Example: Draw all possible stereoisomers, and then look for a plane of symmetry in any of the drawings. The presence of a plane of symmetry indicates a meso compound. Symmetry plane!

14. T HE LAB REPORT … Read the SKILL BUILDER section. Follow instructions given. Molecular models will be provided, or you can bring your own with you to lab!