13147 13 Bromoethane and 2-bromo-2-methylpropane both react with a hot dilute aqueous solution of sodium hydroxide to form the corresponding alcohol. Both mechanisms are classified as nucleophilic substitution but the mechanisms are not identical. Aqueous hydroxide ions behave as nucleophiles and the products are formed via a transition state or an intermediate. (a) Give the IUPAC names of the alcohols formed. [1] (b) (i) Define the term nucleophile. [2] (ii) Show the polarity of the C—Br bond and explain why aqueous hydroxide ions attack bromoethane. C—Br [2] (iii) Draw the structure of the transition state when bromoethane reacts with aqueous sodium hydroxide and suggest why 2-bromo-2-methylpropane does not form a transition state. [2] 13147 [Turn over (c) Draw the mechanism, using curly arrows, for the reaction of 2-bromo-2-methylpropane with aqueous sodium hydroxide. [4]