The trans-substituted tosylate shown is treated with NaCN in DMSO (S_N2), and the resulting nitrile is then reduced with LiAlH4. Which structure is the final amine?

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The trans-substituted tosylate shown is treated with $NaCN$ in DMSO ( $S X_{N} 2$ ), and the resulting nitrile is then reduced with $LiAlH X_{4}$ . Which structure is the final amine?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: B

The compound is trans-4-methylcyclohexyl mesylate (cis/trans assigned by 3D embedding). Cyanide displaces mesylate with inversion, giving the cis nitrile.

LiAlH X_{4}

converts C#N to CH2NH2 without touching the ring carbon, so the product is cis-(4-methylcyclohexyl)methanamine.

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The trans-substituted tosylate shown is treated with NaCN in DMSO (SXN​2), and the resulting nitrile is then reduced with LiAlHX4​. Which structure is the final amine?

Answer: B

More questions on Stereochemical outcome of substitution on drawn chiral substrates

The trans-substituted tosylate shown is treated with $NaCN$ in DMSO ( $S X_{N} 2$ ), and the resulting nitrile is then reduced with $LiAlH X_{4}$ . Which structure is the final amine?