What is the stereochemical outcome of the electrophilic substitution of a chiral aromatic compound?
Practice Questions
1 question
Q1
What is the stereochemical outcome of the electrophilic substitution of a chiral aromatic compound?
Retention of configuration
Inversion of configuration
Racemization
No stereochemical outcome
Electrophilic substitution on a chiral aromatic compound typically leads to racemization due to the formation of a planar sigma complex.
Questions & Step-by-step Solutions
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Q
Q: What is the stereochemical outcome of the electrophilic substitution of a chiral aromatic compound?
Solution: Electrophilic substitution on a chiral aromatic compound typically leads to racemization due to the formation of a planar sigma complex.
Steps: 5
Step 1: Understand that a chiral aromatic compound has a specific 3D arrangement of atoms, making it non-superimposable on its mirror image.
Step 2: Recognize that electrophilic substitution involves the addition of an electrophile to the aromatic ring, which temporarily forms a planar intermediate called a sigma complex.
Step 3: Note that this planar sigma complex can lead to the substitution occurring at different positions on the ring, allowing for both possible configurations (R and S) to form.
Step 4: Realize that because the sigma complex is planar, the reaction does not favor one configuration over the other, resulting in a mixture of both configurations.
Step 5: Conclude that this mixture of configurations is called racemization, meaning the product is a racemic mixture of the two enantiomers.
