Recall that SN2 mechanism is favored:
When H is at the back (dash):
Sodium cyanide reacts with 2-bromobutane in dimethylsulfoxide to form a substitution product. Identify the configuration of the 2-bromobutane structure shown below. Then draw the substitution product formed when this enantiomer reacts with NaCN in DMSO, and indicate the stereochemistry of the product.
Use wedge-and-dash bonds to show stereochemistry, and show explicitly the hydrogen on any asymmetric carbon.
The substitution product is:
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