X is CH3CH(OH)CH2CH3.

1. (a)(i)The reaction between X and alkaline aqueous iodine produces a yellow precipitate. Give the name of the compound formed as a yellow precipitate in this reaction.[1]
2. (a)(ii)Give the name of X.[1]
3. (b)There are three structural isomers of X that are alcohols. Draw the structures of these three isomers of X. [Figure: Empty grid for drawing three structures][2]
4. (c)(i)Two reactions of X are shown. reaction 1 CH3CH(OH)CH2CH3 → CH3COCH2CH3 X reaction 2 ↓ C4H8 Identify the type of reaction involved in reaction 1.[1]
5. (c)(ii)Identify the reagents for reaction 1.[1]
6. (c)(iii)Reaction 2 can be carried out by passing the vapour of X over hot aluminium oxide. The product of reaction 2, C4H8, is actually a mixture of three isomers. Give the full names of the three isomers formed by reaction 2. 1 2 3[3]
7. (d)(i)The reaction of methylpropene, (CH3)2CCH2, with hydrogen bromide, HBr, produces a mixture of two halogenoalkanes. One of the halogenoalkanes, 2-bromo-2-methylpropane, is formed as the major product while 1-bromo-2-methylpropane is formed in small quantities. Complete the mechanism to show the reaction of methylpropene with HBr to form the major product. Include the structure of the intermediate and all necessary charges, dipoles, lone pairs and curly arrows. The structure of 2-bromo-2-methylpropane is not required. [Figure: Incomplete mechanism diagram for reaction of methylpropene with HBr][4]
8. (d)(ii)Explain why 2-bromo-2-methylpropane is the major product of this reaction.[2]

This question uses a diagram from the original paper, which isn't shown here. Open the full paper from the past papers archive to see it.