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Fun Questions inspired by Research Papers

1.

Isocalanone

Isocalanone was isolated by a team of researchers from a Singapore university in 1997 from a tree species found in Sarawak, East Malaysia. (a) Name two functional groups of isocalanone. (b) What is the type of reaction known as when isocalanone reacts with HCN and a catalyst in the cold? (c) With reference to (b), suggest why is the reaction rate of (b) slower than ethanal reacting with HCN and the same catalyst with the same conditions. (d) Draw a possible organic product when isocalanone reacts with aqueous bromine. What is the exact observation of the reaction? (e) Hot aqueous sodium hydroxide is added to isocalanone. Draw the organic product obtained. (f) Cold alkaline potassium manganate(VII) solution is added to isocalanone. Draw the organic product obtained.

2.

M = Cu2+ The above substance is a new organometallic polymer synthesised in 2011 by a group of researchers. This polymer has an unusual feature a metal cation, in this case copper(II) ion, is inserted into the polymer. (a) Write the full electronic configuration of copper(II) ion.

(b) What is the name of the chemical bond between M and each of the 2 nitrogen atoms of the ligand? (c) What is the hybridisation of the carbon atom which has 2 methyl groups attached to it?

(d) With reference to any of the benzene ring in the polymer, the carbon [of the benzyl group] - oxygen bond length is less than the bond length of the C-O bond in methanol. Suggest a reason for that. (e) With reference to VSEPR and transition metal complex chemistry, suggest the shape around M, assuming that no water molecules bind to M. (f) Suggest what happens to the polymer as excess EDTA4- solution is added to 0.1 g of the polymer. (g) With reference to transition metal chemistry, explain briefly why the polymer is coloured.

(h) Would you expect the polymer to be soluble in water? With reference to chemical bonding, briefly explain your reasoning.

3.

[R1 may be ignored] Adenosine triphosphate is used in cellular metabolism as one of the methods of transferring chemical energy between reactions, resulting in redox reactions occurring in the living tissues and organs. The above reaction shows only an adenosine molecule (attached to either a ribose or deoxyribose) reacting with a substituted nitrenium ion, which is singly positively charged. This reaction was carried out in 2007 by a group of researchers in a China university. (a) With reference to either halogenalkane, alkene or arene chemistry, suggest the type of reaction. (b) What is the shape around the nitrogen ion in the nitrenium ion?

(c) Another organic product is also obtained if the reaction conditions are varied. With reference to nitrogen compounds chemistry, deduce a likely structure of the other product. Answers that illustrate that the candidate has understood the underlying mechanisms will be accepted.

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