# Problem: 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. a) (R)-2-bromobutaneb) (S)-2-bromobutaneThe substitution product is: a) R b) S c) racemic d) achiral

🤓 Based on our data, we think this question is relevant for Professor Rowland's class at OLE MISS.

###### FREE Expert Solution

Recall that SN2 mechanism is favored:

• strong nucleophile → NaCN
• aprotic solvent → DPSO

When H is at the back (dash):

• Higher atomic number → higher priority (1- highest, 4 - lowest)
• S – counterclockwise
• R – clockwise
###### Problem Details

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.

a) (R)-2-bromobutane

b) (S)-2-bromobutane

The substitution product is:

a) R

b) S

c) racemic

d) achiral