Q 11-11-23 E
Question
Assign R or S configuration to the following molecule, write the product you would expect from SN2 reaction with NaCN, and assign R or S configuration to the product (green = Cl):
Step-by-Step Solution
Verified Answer
The product expected from SN2 reaction with NaCN and assigning of R/S configuration is,
1S N 2 reaction with NaCN
NaCN is a strong nucleophile in SN2 reaction, and it replaces the halogen group. An inversion of configuration at the chiral centre occurs; if it is S configuration, it changes to R configuration.
2The alkyl bromide from which alkyl acetate is made by S N 2 reaction
The substrate with an S configuration has a secondary allylic chloride group, and a hydroxyl group is primary. A SN2 reaction occurs at the secondary carbon and gives R cyano product because OH is a poor leaving group.
Product expected from SN2 reaction with NaCN
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