What is the stereochemical outcome of the electrophilic substitution of a chiral

Practice Questions

Q1
What is the stereochemical outcome of the electrophilic substitution of a chiral benzene derivative?
  1. Racemic mixture
  2. Enantiomerically pure product
  3. Diastereomers
  4. No stereochemical change

Questions & Step-by-Step Solutions

What is the stereochemical outcome of the electrophilic substitution of a chiral benzene derivative?
  • Step 1: Understand that a chiral benzene derivative has a specific 3D shape due to its chiral center.
  • Step 2: Recognize that the benzene ring is flat (planar), meaning that any electrophilic substitution can occur from either side of the ring.
  • Step 3: When an electrophile attacks the benzene ring, it can do so from above or below the plane of the ring.
  • Step 4: Since the attack can happen from both sides, two different products can form, each with a different stereochemistry.
  • Step 5: These two products are mirror images of each other, leading to a mixture that contains equal amounts of both forms.
  • Step 6: This mixture of two different stereoisomers is called a racemic mixture.
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