You are given a mixture of two enantiomers (C6H12) in lab and are told to do a r

Question

You are given a mixture of two enantiomers (C6H12) in lab and are told to do a reaction with them. The reaction is a catalytic hydrogenation. You isolate a single chiral product. Shown below is the 13C-NMR of both the reactant and product. Determine the structures of the reactant and product. Label all carbons in the spectrum and assign them to carbons in your proposed structure. hint if you have chemdraw you can check your answers

Explanation / Answer

The enantiomeric hexene can be 3-methyl-1-pentene and the product after hydrogenation is 3-methylpentane which is achiral product.

assignment of 13 C NMR

reactant 3-methyl-1-pentene ppm 11 20 30 40 110 145

carbon C-5 C-4 subCH3 C-3 C-2 C-1

product 3-methylpentane ppm 12 21 29 37

carbon C-1,5 C-3 C-2,4 sub. CH3

c

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