1. p. 289

2. Figure 9. 3: The meaning of symmetry plane
Figure 9.3: The meaning of symmetry plane. An object like the flask (a) has a symmetry plane cutting through it, making right and left halves mirror images. An object like a hand (b) has no symmetry plane; the right “half” of a hand is not a mirror image of the left half.
Fig. 9-3, p. 291

6. Chirality at carbon

7. Figure 9.4: The achiral propanoic acid molecule versus the chiral lactic acid molecule. Propanoic acid has a plane of symmetry that makes one side of the molecule a mirror image of the other side. Lactic acid has no such symmetry plane.
Fig. 9-4, p. 292

8. p. 293

9. Figure 9.6: Drawings of sodium ammonium tartrate crystals taken from Pasteur’s original sketches. One of the crystals is “right-handed” and one is “left-handed.”
Fig. 9-6, p. 297

10. Figure 9. 5: Schematic representation of a polarimeter
Figure 9.5: Schematic representation of a polarimeter. Plane-polarized light passes through a solution of optically active molecules, which rotate the plane of polarization.
Fig. 9-5, p. 295

11. The nose knows
S(+)-carvone is found in caraway seeds and mandarin orange peel oil and smells like caraway.
R(–)-carvone is extracted from spearmint and kuromoji oils and smells like spearmint.
Gingergrass oil contains a mixture of both enantiomers.

12. p. 325

13. Fischer Projections

14. Stereoisomers with multiple chiral centers:

15. Stereoisomers with multiple chiral centers:

16. Stereoisomers with multiple chiral centers:
Mirror
plane

17. Stereoisomers with multiple chiral centers:
Mirror
plane

18. Stereoisomers with multiple chiral centers: Enantiomers
Mirror
plane
E = Enantiomer

19. Stereoisomers with multiple chiral centers: Enantiomers
Mirror
plane
E = Enantiomer

20. Stereoisomers with multiple chiral centers: Enantiomers
Mirror
plane
E = Enantiomer

21. Stereoisomers with multiple chiral centers: Enantiomers
Mirror
plane
E = Enantiomer

22. Stereoisomers with multiple chiral centers: Enantiomers & Diastereomers
Mirror
plane
E = Enantiomer
D = Diastereomer

23. Stereoisomers with multiple chiral centers: Enantiomers & Diastereomers
Mirror
plane
E = Enantiomer
D = Diastereomer

24. Stereoisomers with multiple chiral centers: Enantiomers & Diastereomers
Mirror
plane
E = Enantiomer
D = Diastereomer

25. Stereoisomers with multiple chiral centers: Enantiomers & Diastereomers
E = Enantiomer
D = Diastereomer

26. What is the relationship? Fill in each box with E or D
E = Enantiomer
D = Diastereomer

27. p. 325

28. Figure 9.11: A symmetry plane through the C2–C3 bond of meso-tartaric acid makes the molecule achiral.
Fig. 9-11, p. 305

29. p. 305

30. Stereoisomers with multiple chiral centers: meso - compounds

32. p. 314