Compounds J, K, L and M are isomers of each other with the molecular formula C₉H₁₁NO. All four isomers contain a benzene ring. Two of the isomers contain a chiral centre. The results of six tests carried out on J, K, L and M are shown in the table. ``` observations with each isomer test J K L M 1 add cold HCl(aq) soluble soluble soluble insoluble 2 add 2,4-DNPH reagent orange ppt. orange ppt. orange ppt. no reaction 3 add NaOH(aq) + I2(aq) pale yellow ppt. no reaction pale yellow ppt. no reaction 4 warm with Fehling's solution no reaction red ppt. no reaction no reaction 5 heat with NaOH(aq) no reaction no reaction no reaction P(C7H7N) and Q(C3H5ONa) produced 6 diazotization and addition of alkaline phenol no dye produced orange dye produced no dye produced no dye produced ```

1. (a)Use the experimental results in the table above to determine the group(s), in addition to the benzene ring, present in each of the four isomers J, K, L and M. Complete the table below, identifying the group(s) present in each isomer. [Figure X.X][5]
2. (b)(i)Name the type of reaction occurring in test 5 that converts M into P + Q.[1]
3. (b)(ii)Suggest structures for compounds P and Q. P (C₇H₇N) Q (C₃H₅ONa)[2]
4. (c)Isomers J, K, L and M all have the molecular formula C₉H₁₁NO. Use the information in (a) to suggest a structure for each of these isomers and draw these in the boxes. Draw circles around all chiral centres in K and L. [Figure X.X][5]
5. (d)Compound N is another isomer which has the same molecular formula C₉H₁₁NO and also contains a benzene ring. N contains the same functional group as M. When heated with NaOH(aq), N produces ethylamine and a sodium salt W. Suggest the structure of W. [Figure X.X][1]

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