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. The substitution product is: a) (R)-2-bromobutane b) (S)-2-bromobutaneThe substitution product is:a) R b) S c) racemicd) achiral

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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. The substitution product is: 

a) (R)-2-bromobutane 

b) (S)-2-bromobutane


The substitution product is:

a) R 

b) S 

c) racemic

d) achiral

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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Substitution Comparison concept. You can view video lessons to learn Substitution Comparison. Or if you need more Substitution Comparison practice, you can also practice Substitution Comparison practice problems.

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Based on our data, we think this problem is relevant for Professor Lever's class at MIZZOU.