Which of the following statements about stereochemistry is true for the reaction of 2-bromobutane with NaOH?
Practice Questions
1 question
Q1
Which of the following statements about stereochemistry is true for the reaction of 2-bromobutane with NaOH?
Only R isomer is formed
Only S isomer is formed
Both R and S isomers are formed
No stereoisomers are formed
The reaction can lead to both R and S isomers due to the nature of the nucleophilic substitution mechanism.
Questions & Step-by-step Solutions
1 item
Q
Q: Which of the following statements about stereochemistry is true for the reaction of 2-bromobutane with NaOH?
Solution: The reaction can lead to both R and S isomers due to the nature of the nucleophilic substitution mechanism.
Steps: 7
Step 1: Understand that stereochemistry refers to the 3D arrangement of atoms in molecules.
Step 2: Recognize that 2-bromobutane is a chiral molecule, meaning it has non-superimposable mirror images (R and S isomers).
Step 3: Identify that NaOH is a strong nucleophile that can attack the carbon atom bonded to the bromine in 2-bromobutane.
Step 4: Learn that the reaction can occur through two different mechanisms: SN1 and SN2.
Step 5: In the SN2 mechanism, the nucleophile attacks from the opposite side of the leaving group (bromine), leading to inversion of configuration, which can produce the opposite isomer.
Step 6: In the SN1 mechanism, the leaving group (bromine) departs first, creating a planar carbocation that can be attacked by the nucleophile from either side, leading to both R and S isomers.
Step 7: Conclude that the reaction of 2-bromobutane with NaOH can produce both R and S isomers due to the nature of the nucleophilic substitution mechanism.
