Phenylethanone is an important chemical with many uses. phenylethanone CH₃ O C

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]
2. (b)(i)reagent: chlorine gas at 10°C in the presence of ultra-violet light[2]
3. (b)(ii)reagent: a mixture of concentrated nitric and sulfuric acids at 50°C[2]
4. (b)(iii)reagent: bromine water[1]
5. (c)(i)Name the mechanism of this reaction. [1][1]
6. (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. phenylethanone intermediate product [4][4]
7. (d)(i)Draw the structure of compound D in the box. [1][1]
8. (d)(ii)Identify a suitable reagent for step 1. [1][1]
9. (d)(iii)Identify a suitable reagent for step 2. [1][1]
10. (d)(iv)State the number of peaks in the C-13 NMR spectrum of phenylethene. [1][1]
11. (d)(v)Suggest C-13 chemical shift ranges expected for the different types of carbon environment in phenylethanone. [2][2]

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