1,3-dichloropropan-2-ol can be made by reacting M. [Figure showing M reacting to form 1,3-dichloropropan-2-ol]

1. (a)(i)Give the systematic name of M.[1]
2. (a)(ii)Name the functional group present in M that changes during this reaction.[1]
3. (a)(iii)State a suitable reagent for this reaction.[1]
4. (b)Separate samples of 1,3-dichloropropan-2-ol and 3-chloropropane-1,2-diol are heated with excess acidified Cr2O72- until there is no further reaction. In each reaction, a different organic product, Q or R, is made. [Figure showing structures of 1,3-dichloropropan-2-ol and 3-chloropropane-1,2-diol leading to Q and R] Q and R are tested separately with 2,4-dinitrophenylhydrazine solution, 2,4-DNPH, and sodium carbonate solution, Na2CO3(aq). Complete the table to give any relevant observations. If no reaction occurs, write 'no visible change'. [Table with reagent, observation with Q, observation with R][4]
5. (c)Citric acid can be made from M in a four-step reaction. [Figure showing a 4-step reaction sequence from M to citric acid] Complete the table for each step of the reaction sequence to identify: • the reagents and conditions required • the type of reaction. [Table with step, reagent and conditions, type of reaction][5]

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.