Compound T is made by a three-stage synthesis. [Figure showing a synthesis pathway: phenylethanoic acid -> (stage 1) Compound R (C₆H₅CH₂COCl) -> (stage 2) Compound S (C₆H₅CH₂CONHCH₂CH₃) -> (stage 3) Compound T]

1. (a)In stage 1, phenylethanoic acid reacts with a suitable reagent to form compound R. [Figure showing phenylethanoic acid reacting to form R] Suggest a suitable reagent for stage 1.[1]
2. (b)(i)In stage 2, compound R reacts with ethylamine to form compound S. [Figure showing R reacting with C₂H₅NH₂ to form S] Name the functional group formed in stage 2.[1]
3. (b)(ii)Identify the other product formed in stage 2.[1]
4. (c)(i)In stage 3, compound S reacts with a suitable reagent to form compound T. [Figure showing S reacting to form T] State the formula of a suitable reagent for stage 3.[1]
5. (c)(ii)Name the type of reaction that occurs in stage 3.[1]
6. (d)(i)The relative abundance of the molecular ion peak in the mass spectrum of ethylamine is 62. Calculate the relative abundance of the M+1 peak in the mass spectrum of ethylamine.[1]
7. (d)(ii)The mass spectrum of compound T contains several fragments. The m/e values of two of these fragments are 29 and 91. Draw the structures of the ions responsible for these peaks.[2]
8. (e)(i)The proton (¹H) NMR spectrum of compound T shows hydrogen atoms in different environments. Six of these environments are shown on the structure using letters a, b, c, d, e and f. [Figure of Compound T: C₆H₅-CH₂-CH₂-NH-CH₂-CH₃ with protons labelled a, b, c, d, e, f] Use the letters a, b, c, d, e and f to answer the questions that follow. The questions relate to the proton (¹H) NMR spectrum of T. Proton d does not cause splitting of the peaks for protons c or e under the conditions used. Each answer may be one, or more than one, of the letters a, b, c, d, e and f. Identify the proton or protons with a chemical shift (δ) in the range 6.0 to 9.0.[1]
9. (e)(ii)Identify the proton or protons whose peak will disappear if D₂O is added.[1]
10. (e)(iii)Identify the proton or protons whose peak is a triplet.[1]
11. (e)(iv)Identify the proton or protons with the lowest chemical shift (δ).[1]

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.