Question

Draw the organic product of the following reaction between (1S,3S)-1-chloro-3-methylcyclopentane and methanethiol in the presence of sodium hydroxide. 

Answer 1

it is a SN2 reaction. The 1S chloro is replaced with a 1R-thiomethoxy group.

Answer 2

The structure of the starting material has a pentagon with -Cl at the 12 o'clock position attached by a dashed line. -CH3 is attached at the 5 o'clock position by a solid wedge. The reaction is a Walden inversion, resulting in (1R,3S) 1-methylthio-3-methylcyclopentane. The CH3S- is now attached by a solid wedge.

Answer 3

Answer 4

R,S

The structure of the starting material has a pentagon with -Cl at the 12 o'clock position attached by a dashed line. -CH3 is attached at the 5 o'clock position by a solid wedge. The reaction is a Walden inversion, resulting in (1R,3S) 1-methylthio-3-methylcyclopentane. The CH3S- is now attached by a solid wedge.

Answer 5

Answer 6