Your team has been asked to devise a synthesis of the tertiary alcohol 2-cyclohexyl-2-butanol, A. Your laboratory is well stocked with the usual organic and inorganic reagents and solvents. An inventory check reveals that there are many appropriate bromoalkanes and alcohols on hand. As a group, analyze alcohol A retrosynthetically and propose all possible strategic disconnections. Check the inventory to see if a particular route is feasible in terms of available starting materials. Then divide the proposed routes evenly among yourselves to evaluate the merits or pitfalls of these strategies. Write a detailed synthetic plan based on your chosen retrosynthesis for the synthesis of 2-cyclohexyl-2-butanol. Reconvene to defend or reject these plans. Finally, take into consideration the prices of your starting materials. Which one of your routes to A is the cheapest?

Target Molecule Inventory (Price) 2-Bromobutane ($57/500 g) Bromocyclohexane ($91/kg Bromoethane ($36/kg) Bromomethane (S640/kg) 2-Butanol (S31/kg) Cyclohexanol ($16/kg) 1-Cyclohexylethanol (S106/25 g) Cyclohexylmethanol ($21/25 g) Bromomethyl)cyclohexane ($137/100 g) 2-Cyclohexyl-2-butanol