Phenylethanone is an important chemical with many uses. phenylethanone [Figure of phenylethanone structure]

1. (a)Phenylethanone can be synthesised using benzene as one of the starting materials. Identify the other reagents used and describe any essential reaction conditions.[2]
2. (b)Phenylethanone is treated separately with three reagents. Complete the table, for each reagent, to give the structural formula of one organic product formed and the name of the mechanism involved. If there is no reaction you should write 'no reaction'.[5]
3. (c)(i)Phenylethanone reacts with HCN in the presence of a small amount of NaCN. Name the mechanism of this reaction.[1]
4. (c)(ii)Draw the mechanism of this reaction below. Include all relevant charges, dipoles, lone pairs and curly arrows. Your mechanism should show the catalytic role of CN⁻ ions.[4]
5. (d)(i)Phenylethanone can be used as a starting material to make phenylethene in a two-step synthesis. [Figure showing phenylethanone -> D -> phenylethene] Draw the structure of compound D in the box.[1]
6. (d)(ii)Identify a suitable reagent for step 1.[1]
7. (d)(iii)Identify a suitable reagent for step 2.[1]
8. (d)(iv)State the number of peaks in the C-13 NMR spectrum of phenylethene.[1]
9. (d)(v)Suggest C-13 chemical shift ranges expected for the different types of carbon environment in phenylethanone.[2]

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