Optical Activity
Mediumchemistry
2-Bromobutane undergoes SN1 to give racemic mixture because:
Select the correct option:
Solution
Incorrect! Answer:
Planar carbocation allows attack from either side
- Intermediate: SN1 proceeds through the formation of a carbocation.
- Geometry: The secondary carbocation formed from 2-bromobutane is planar (sp2 hybridized).
- Accessibility: Since the carbon is flat, the nucleophile (e.g.,OH−) can attack from either the front face or the back face with equal probability.
- Products:
- Attack from front → Product with same configuration (Retention).
- Attack from back → Product with inverted configuration (Inversion).
- Stereochemistry: A 50:50 mixture of d and l isomers is formed, resulting in a racemic mixture (optical inactivity).
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About This Question
- Subject
- chemistry
- Chapter
- halogen organics
- Topic
- optical activity
- Difficulty
- Medium
- Year
- 2025
Solution
Correct Answer:
Planar carbocation allows attack from either side
- Intermediate: SN1 proceeds through the formation of a carbocation.
- Geometry: The secondary carbocation formed from 2-bromobutane is planar (sp2 hybridized).
- Accessibility: Since the carbon is flat, the nucleophile (e.g.,OH−) can attack from either the front face or the back face with equal probability.
- Products:
- Attack from front → Product with same configuration (Retention).
- Attack from back → Product with inverted configuration (Inversion).
- Stereochemistry: A 50:50 mixture of d and l isomers is formed, resulting in a racemic mixture (optical inactivity).
This medium difficulty chemistry question is from the chapter halogen organics, covering the topic of optical activity. It appeared in the 2025 exam.
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