The epoxide shown is treated with $NaN X_{3}$ and $NH X_{4} Cl$ in aqueous ethanol. Relative configuration is what matters; ignore which enantiomer is drawn. Which structure is the major product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: B

The compound is cyclohexene oxide. Azide attacks one carbon from the back side (anti opening) and the oxygen remains on the other carbon, so the new C-N and C-O bonds are trans. The product is trans-2-azidocyclohexanol (S,S shown; the racemate forms). The cis isomer would need syn opening.

Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on Epoxide and ether cleavage regiochemistry on drawn structures

Previous questionNext question

The epoxide shown is treated with NaNX3​ and NHX4​Cl in aqueous ethanol. Relative configuration is what matters; ignore which enantiomer is drawn. Which structure is the major product?

Answer: B

More questions on Epoxide and ether cleavage regiochemistry on drawn structures

The epoxide shown is treated with $NaN X_{3}$ and $NH X_{4} Cl$ in aqueous ethanol. Relative configuration is what matters; ignore which enantiomer is drawn. Which structure is the major product?