4 (a) 2-methylpropene reacts with HCl(g) at room temperature. The major organic product is 2-chloro-2-methylpropane. (i) Complete Fig. 4.1 to show the structure of the intermediate and mechanism for this reaction. Include charges, dipoles, lone pairs of electrons and curly arrows as appropriate. [Figure 4.1] (ii) Explain why, in this reaction, 2-chloro-2-methylpropane is produced at a higher yield than 1-chloro-2-methylpropane. (b) Two bottles labelled Q and M each contain a straight-chain halogenoalkane with molecular formula C4H9X, where X represents Cl, Br or I. A sample from each bottle is added to separate samples of equal amounts of aqueous silver nitrate in ethanol. In each reaction, the same organic product, T, and a precipitate are made, as shown in Fig. 4.2. [Figure 4.2] Table 4.1 describes the colour of each of the precipitates made. Table 4.1 | halogenoalkane added to AgNO3(aq) in ethanol | colour of precipitate | |---|---| | Q | white | | M | yellow | (i) Identify the functional group present in T and name the type of reaction that occurs using the information in Fig. 4.2 and Table 4.1. functional group in T type of reaction (ii) Construct an ionic equation to describe the formation of the yellow precipitate produced when M reacts with AgNO3(aq) in ethanol. (iii) Describe which reagent, Q or M, will produce a precipitate more quickly when each is added to AgNO3(aq) in ethanol. Explain your answer. reagent (iv) When pure T is added to alkaline I2(aq), a yellow precipitate and an anion, L, are made. Identify the anion L. (v) Deduce the structure of the straight-chain halogenoalkane M.