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CHE430/495 ASSIGNMENT 1
Question 1 (PO1, CO1, C1, C2) a) Draw the structures of the following compounds showing every orbital involved in the sigma (σ) and pi (π) bonds. i) CH 3 COCH 3 ii) CHCCH 3 (4 marks) b) Describe the type of nucleophilic substitution that occur in the reactions below: i) ii) iii) (3 marks) c) Calculate the degree of unsaturation in the following formulas, and draw a possible structure containing two rings. i) C 6 H 8 ii) C 10 H 4 Cl 2 Br 2 iii) C 9 H 12 NClO 2 (6 marks)
Question 2 (PO1, CO2, C3, C4) a) Sketch an energy diagram of the different conformers of 2,3-dimethylbutane viewed from C2-C3 bond. Select the most stable conformer. (8 marks) b) Explain the acidity of terminal alkanes, alkenes and alkynes. (4 marks) c) Compound A has the formula C 10 H 16. On catalytic hydrogenation over palladium, it reacts with only 1 molar equivalent of H 2 to yield C. Compound A also undergoes reaction with ozone, followed by zinc treatment, to yield a symmetrical diketone, B (C 10 H 16 O 2 ). By showing the reaction steps, predict the structures of A, B and C. (4 marks) Question 3 (PO1, CO1, CO2, C2, C3, C4) a) Identify compounds A-E. Br 2 Hg(OAc) 2 , EtOH NaBH 4 BH 3 , THF H 2 O 2 , NaOH H 2 Pd/C warm, conc. KMnO 4 H 3 O+
A
B
C
D
E
(10 marks) b) Name compounds B and D from question 7 according to IUPAC. (2 marks) c) Show the reaction mechanism of cyclohexene with Br 2. (3 marks) d) Pentanedial could be produced from alkene oxidation. Determine whether cyclopentene or 5-decene would be more suitable to be used as a starting material in the ozone oxidation. Justify your answer with complete chemical reactions. (6 marks)
