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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

Chirality at carbon

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

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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

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

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.

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Fischer Projections

Stereoisomers with multiple chiral centers:

Stereoisomers with multiple chiral centers:

Stereoisomers with multiple chiral centers: Mirror plane

Stereoisomers with multiple chiral centers: Mirror plane

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

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

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

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

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

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

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

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

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

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

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Stereoisomers with multiple chiral centers: meso - compounds

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