The total number of isomeric monochloro derivatives (including stereoisomers) formed on free radical monochlorination of 1,1-dimethylcyclohexane is _________

Step-by-step solution

The given compound is 1,1-dimethylcyclohexane. It has a plane of symmetry passing through C1 and C4. The non-equivalent positions for monochlorination are: 1) The methyl groups at C1: Chlorination of either methyl group gives 1-(chloromethyl)-1-methylcyclohexane. This molecule is achiral because the two paths around the ring from C1 to C4 are identical (1 isomer). 2) The C2 (or C6) position: Chlorination gives 2-chloro-1,1-dimethylcyclohexane. The C2 carbon is a chiral center, so it exists as a pair of enantiomers