alcohol reaction
In this conversion compare starting material with product .Observe changes to be made
1) Get rid of oxygen --convert it to alcohol and do dehydration which gives alkene or Wolf Kishner or Clemmensons reduction which will give cyclohexane.(Kishner or Clemmensons Reduction will not give us reactive compound so will be of no use.)
2.Add one methyl group which we all know can be done using CH3MgBr which solves two problems -First you get methyl group on desired position and then alcohol which can be dehydrated to give alkene
3) Now add HBr by anti-marks rule to get Br on less substituted carbon.
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