(a) Identify the chiral molecule in the pair shown in the figure (3-methylbutan-2-ol and 2,4-dimethylpentan-3-ol). (b) Write the structure of the product when chlorobenzene is treated with methyl chloride in the presence of sodium metal and dry ether. (c) Write the structure of the alkene formed by dehydrohalogenation of 1-bromo-1-methylcyclohexane with alcoholic KOH.(i) 3-methylbutan-2-ol(ii) 2,4-dimethylpentan-3-ol
Solution
(a) In 3-methylbutan-2-ol, CH3–\*CH(OH)–CH(CH3)2, the carbinol carbon holds CH3, OH, H and isopropyl — four different groups ⇒ \textbf{chiral}. 2,4-Dimethylpentan-3-ol is symmetric about C-3 (two identical isopropyls) — achiral. (b) Wurtz–Fittig reaction: