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Question 1

a) Draw the structures of the following compounds showing every orbital involved in the sigma (σ) and pi (π) bonds.

i) CH3COCH3
ii) CHCCH3

b) Describe the type of nucleophilic substitution that occurs in the reactions below:

Calculate the degree of unsaturation in the following formulas, and draw a possible structure containing two rings.

i) C6H8
ii) C10H4Cl2Br2
iii) C9H12NClO2

Question 2

a) Sketch an energy diagram of the different conformers of 2,3-dimethyl butane viewed from the C2-C3 bond. Select the most stable conformer.

b) Explain the acidity of terminal alkanes, alkenes, and alkynes.

c) Compound A has the formula C10H16. On catalytic hydrogenation over palladium, it reacts with only 1 molar equivalent of H2 to yield C. Compound A also undergoes reaction with ozone, followed by zinc treatment, to yield a symmetrical diketone, B (C10H16O2). By showing the reaction steps, predict the structures of A, B and C.

Question 3

a) Identify compounds A-E.

Name compounds B and D from question 7 according to IUPAC.

c) Show the reaction mechanism of cyclohexene with Br2.

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 ozone oxidation. Justify your answer with complete chemical reactions.

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