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Optical activity and enantiomeric excess

Why one hand rotates light one way, its mirror the other, and how ee measures the imbalance.

Quick answer A chiral molecule is optically active: one enantiomer rotates plane-polarized light clockwise (+) and its mirror image rotates it equally counterclockwise (−), so a 50:50 racemic mixture shows zero net rotation. Enantiomeric excess, ee = |%major − %minor| = (observed [α] / pure [α]) × 100%, measures how one-handed a sample is.

1. A chiral molecule is optically active — it rotates plane-polarized light.

(R)-2-butanol — (+) rotation
(S)-2-butanol — (−) rotation

2. One enantiomer is dextrorotatory (+) and its mirror image is levorotatory (−) by an equal amount.

(R)-lactic acid
(S)-lactic acid — mirror image

3. The magnitude of rotation is the specific rotation [α], a physical constant of each pure enantiomer.

Alanine — a single [α] value at fixed T, λ, concentration

4. A racemic mixture (exactly 50:50) is optically inactive because the opposite rotations cancel.

(R)-2-butanol
(S)-2-butanol — equal amounts sum to zero net rotation

5. Enantiomeric excess measures how one-handed a sample is: ee = |%major − %minor| = (observed [α] / pure [α]) × 100%.

Glyceraldehyde — a 75:25 sample gives 50% ee

6. Note (+)/(−) is measured in the lab, while (R)/(S) is assigned from structure — the two are unrelated.

(R)-lactic acid — sign of rotation must be measured, not predicted

Summary: Chiral = optically active · (+) dextro vs (−) levo, equal & opposite · [α] is a constant · racemic (50:50) and meso = inactive · ee = |%major − %minor| = observed/pure × 100% · (+)/(−) measured, (R)/(S) assigned.

Quiz yourself

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It contains equal amounts of both enantiomers, whose (+) and (−) rotations are equal and opposite, so they cancel exactly.

ee = |75 − 25| = 50% enantiomeric excess.

No. (R)/(S) is assigned from structure by priority rules; (+)/(−) is a measured physical property. There is no fixed correspondence between them.

ee = (20 / 40) × 100% = 50% ee (a 75:25 ratio favoring the (+) enantiomer).

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