What is the stereochemical outcome of the electrophilic substitution of a chiral benzene derivative?

Practice Questions

1 question

Racemic mixture
Enantiomerically pure product
Diastereomers
No stereochemical change

Questions & Step-by-step Solutions

1 item

Q: What is the stereochemical outcome of the electrophilic substitution of a chiral benzene derivative?

Solution: Electrophilic substitution on a chiral benzene derivative typically leads to a racemic mixture due to the planar nature of the benzene ring.

Steps: 6

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.

What is the stereochemical outcome of the electrophilic substitution of a chiral benzene derivative?

Practice Questions

Questions & Step-by-step Solutions

Related Questions

On a scale of 0–10, how likely are you to recommend The Soulshift Academy?