M reacts to form R by the addition of one reagent, as shown in Fig. 5.1. [Figure 5.1] Identify the reagent and conditions for this reaction.

1. (a)M reacts to form R by the addition of one reagent, as shown in Fig. 5.1. [Figure 5.1] Identify the reagent and conditions for this reaction.[1]
2. (b)(i)R is also made from M by two steps, as shown in Fig. 5.2. [Figure 5.2] Identify the reagents and conditions for steps 1 and 2 in Fig. 5.2. step 1 step 2[2]
3. (b)(ii)Name the mechanism for step 1 in Fig. 5.2.[1]
4. (c)The infrared spectrum of R is shown in Fig. 5.3. [Figure 5.3] Table 5.1 bond functional groups containing the bond characteristic infrared absorption range (in wavenumbers)/cm⁻¹ C–O hydroxy, ester 1040–1300 C=C aromatic compound, alkene 1500–1680 C=O amide 1640–1690 carbonyl, carboxyl 1670–1740 ester 1710–1750 C≡N nitrile 2200–2250 C–H alkane 2850–2950 N–H amine, amide 3300–3500 O–H carboxyl 2500–3000 hydroxy 3200–3650 Use the absorptions in the region above 1500cm¯¹ in Table 5.1 when answering this question. • Add F to Fig. 5.3 to identify the peak that is present in an infrared spectrum of both Q and R. Identify the bond that corresponds to the absorption for F. • Add G to Fig. 5.3 to identify the peak that is not present in an infrared spectrum of Q. Identify the bond that corresponds to the absorption for G.[2]
5. (d)(i)Y is made from Q in a three-step reaction. [Figure 5.4] Draw the structure of W in the box in Fig. 5.4.[1]
6. (d)(ii)In step 2, W is heated with HCl(aq) to produce X and an inorganic product. Identify the formula of the inorganic product.[1]
7. (d)(iii)In step 3, X reacts with reducing agent Z to produce Y. Complete the equation for the reaction of X with Z. Use a molecular formula to represent the organic product. Use [H] to represent one atom of hydrogen from Z. C8H12O4 + ......[H] →[1]
8. (d)(iv)Identify Z.[1]

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