11382 13 Propene is an important building block for a large number of chemicals. At low temperatures, propene will react with chlorine in an electrophilic addition reaction. (a) (i) Explain the term electrophile. [2] (ii) Draw a flow scheme to show the mechanism for the reaction between propene and chlorine using curly arrows. [4] (b) At 500 °C in the presence of ultraviolet light, propene will react with chlorine in a similar way to the reaction of propane with chlorine radicals. The product formed is allyl chloride (CH2=CHCH2Cl). Outline the mechanism of the reaction between propene and chlorine giving equations for the initiation, propagation and termination steps. Initiation equation Propagation equations Termination equation [4] 11382 [Turn over (c) (i) Two reactions of allyl chloride are shown. Fill in the structures of Compounds A, B and C. More of compound B is formed than compound C. H H C=C H CH2Cl Compound A Compound C H2/Ni Reaction 1 Reaction 2 HCl Compound B + [3] (ii) Explain why compounds B and C are not formed in equal amounts. [2] (iii) Compound B reacts slowly in humid conditions to form compound D which contains the following percentage masses: C, 40.0%; H, 7.0%; O, 53.0%. The relative formula mass of the compound is 90. Deduce the molecular formula of compound D. [3] 11382 (d) Allyl chloride will undergo an hydrolysis reaction with aqueous sodium hydroxide similar to halogenoalkanes. (i) Draw the structural formula of the organic product formed in this reaction. Show all the bonds present. [2] (ii) Name the inorganic product formed during this hydrolysis reaction. [1] (e) Allyl chloride has a structural isomer which exists as geometrical isomers. Draw and label these geometrical isomers. [3] 11382 [Turn over (f) Allyl chloride is highly flammable. When it burns, one of the products formed is a corrosive gas. (i) Define the term molar gas volume. [1] (ii) 1.50 g of this corrosive gas occupies a volume of 0.986 dm3 at 293 K and 1 atmosphere pressure. Use this information to calculate the relative molecular mass of the gas and suggest its identity. [3]