There are four possible structural isomers of C8H10 that contain a benzene ring. Draw the skeletal formulae of the four structural isomers in the appropriate boxes. The number of peaks observed in the carbon-13 (13C) NMR spectrum of each compound is given. isomer 1 three peaks in 13C NMR isomer 2 four peaks in 13C NMR isomer 3 five peaks in 13C NMR isomer 4 six peaks in 13C NMR

1. (a)There are four possible structural isomers of C8H10 that contain a benzene ring. Draw the skeletal formulae of the four structural isomers in the appropriate boxes. The number of peaks observed in the carbon-13 (13C) NMR spectrum of each compound is given. isomer 1 three peaks in 13C NMR isomer 2 four peaks in 13C NMR isomer 3 five peaks in 13C NMR isomer 4 six peaks in 13C NMR[4]
2. (b)A three-step synthesis of X (C10H10O) from benzene is suggested as shown. W Cl(CH2)3CO2H AlCl3 step 1 step 2 step 3 AlCl3 Cl X (C10H10O)
3. (b)(i)Step 1 is the alkylation of benzene by electrophilic substitution. Use R-Cl to represent Cl(CH2)3CO2H. Write an equation for the formation of an electrophile from R-Cl and AlCl3. ...........................................................................................................................................................[1]
4. (b)(ii)Deduce and draw the structures of W and X in the boxes.[2]
5. (b)(iii)Suggest the reagents and conditions for step 2. ...........................................................................................................................................................[1]
6. (b)(iv)Complete the mechanism for the reaction of benzene with the electrophile formed in (b)(i). Include all relevant charges and curly arrows showing the movement of electron pairs. Draw the structure of the intermediate. [Figure for mechanism][3]

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