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4.6.2Unit 4. Rates, Equilibria and Further Organic Chemistry

Racemates and Optical Activity — IAL Edexcel Linear (Chemistry) Revision Notes & Topical Questions

5 min read 4 parts Lesson 43 of 56 Unit quiz

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Curriculum Equation Key معادلة تفاعل تكوين الإستر (الأسترة) - Esterification Reaction EquationFast Exam Solution
R-COOH + R2-OH ⇌ (conc. H₂SO₄) R-COO-R2 + H₂O
Word Equation & Conditions: حمض كربوكسيلي + كحول (في وجود حمض الكبريتيك المركز كعامل حفاز ونازع للماء) ⇌ إستر + ماء
Location & Specifications: الكيمياء العضوية للثانوية العامة والتحصيلي و Edexcel Chemistry.
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Part 1 of 4Racemic Mixtures

A racemate contains the two enantiomers in equal amounts.

Definition
  • Definition A racemic mixture, or racemate, contains equal amounts of the two enantiomers of a chiral compound.
No net rotation
  • No net rotation The rotation caused by one enantiomer is cancelled by the equal and opposite rotation from the other.
Optically inactive
  • Optically inactive A racemate has no effect on plane-polarised light overall, even though each molecule is chiral.
Naming
  • Naming Racemates are sometimes written with the prefix (±) to show an equimolar mixture.
Pharmaceutical use
  • Pharmaceutical use Some chiral medicines are sold as racemates even though only one of the two enantiomers may give the useful biological effect.

Part 2 of 4Why Racemates Form

Ordinary chemical syntheses have no preference for one mirror-image form.

1
A reaction that creates a chiral centre from a flat, planar arrangement allows attack from either face of the molecule.
2
Each face is equally likely to be attacked, so both enantiomers are produced at the same rate.
3
The product mixture is therefore racemic and has no optical activity.
4
Producing a single enantiomer needs a chiral catalyst, an enzyme or separation of the mixture afterwards.

Part 3 of 4Importance in Medicine

Importance in Medicine
Drug action
  • Drug action Receptors and enzymes in the body are chiral, so one enantiomer of a drug may fit while the other does not.
Different effects
  • Different effects Sometimes one enantiomer is the active drug and the other is inactive or causes unwanted side effects.
Cost
  • Cost Separating or selectively synthesising a single enantiomer is expensive, which raises the price of a medicine.
Regulation
  • Regulation Pharmaceutical companies must study each enantiomer separately before a chiral drug is approved for use.

Part 4 of 4Exam Checklist & Tips

4.6.2 – Key Points for the Exam

  • Racemate Equimolar mixture of two enantiomers.
  • Optically inactive Does not rotate plane-polarised light.
  • Enantiomerically pure Containing only a single enantiomer.
  • Planar Having all atoms in one flat plane.

Common Mistakes

  • Saying a racemate is optically inactive because the molecules are not chiral.
  • Forgetting that the mixture must have exactly equal amounts of each enantiomer.
  • Claiming enantiomers react differently with all reagents.
  • Assuming synthesis always gives a single optical isomer.

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