P, Q and R all have the molecular formula C₃H₆O. They are all structural isomers of each other. P and Q each contain an oxygen atom bonded directly to a carbon atom that is sp² hybridised. R contains an oxygen atom bonded directly to a carbon atom that is sp³ hybridised.

1. (a)(i)Explain the meaning of the term structural isomers.[2]
2. (a)(ii)Explain how sp² and sp³ hybridisation can occur in carbon atoms. sp² hybridisation sp³ hybridisation[2]
3. (a)(iii)State the bond angles normally associated with each type of hybridisation in carbon atoms. sp² sp³[2]
4. (b)(i)R contains two different functional groups, one of which is an alkene group. R reacts with cold, dilute, acidified manganate(VII) ions to form propane-1,2,3-triol. [Figure 4.1: Displayed formula of propane-1,2,3-triol] Give the displayed formula of R.[1]
5. (b)(ii)State the type of reaction and what you would observe when R reacts with bromine water.[2]
6. (b)(iii)Draw the structure of the product formed when R reacts with bromine water.[1]
7. (b)(iv)Identify the gaseous product formed when R reacts with hot, concentrated, acidified manganate(VII) ions.[1]
8. (c)(i)P and Q (C₃H₆O) both form an orange precipitate when reacted with 2,4-DNPH. Only Q produces a yellow precipitate when reacted with alkaline aqueous iodine. Name P and Q. P Q[2]
9. (c)(ii)Identify the yellow precipitate formed by the reaction of Q with alkaline aqueous iodine.[1]
10. (d)(i)P and Q each react with hydrogen cyanide to form a single product. The product formed from P exists as a pair of optical isomers. The product formed from Q does not exhibit optical isomerism. Explain the meaning of the term optical isomers.[2]
11. (d)(ii)Ethanal, CH₃CHO, also reacts with hydrogen cyanide. The product of this reaction is CH₃CH(OH)CN. Draw the mechanism of this reaction. Include all necessary charges, dipoles, lone pairs and curly arrows.[3]