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recitation6 - 3 Which structure is most stable(1 pt 4...

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Page 1 of 2 CH 235-2E Spring, 2012 Organic Chemistry I Recitation Problem Set #6 1. The heat of combustion of neopentane (an isomer of pentane) is 3250 kJ/mol; that of pentane is 3269 kJ/mol. Which statement best describes the relative stability of these two compounds? (1 pt) (A) Pentane and neopentane are isomers and therefore exhibit the same stability. (B) Pentane is more stable than neopentane by 19 kJ/mol. (C) Neopentane is more stable than pentane by 19 kJ/mol. (D) No statement can be made regarding relative stability. 2. Look at the following reaction coordinate diagram and answer the questions (2 pts). (a) Is Δ G o for the reaction positive or negative? Label it on the diagram. (b) How many steps are involved in the reaction? (c) How many transition states are there? Label them on the diagram. (d) How many intermediates are there? Label them on the diagram. (e) Which step is most exergonic? (f) Which step is slowest? (g) Which step is the rate-determining step?
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Unformatted text preview: 3. Which structure is most stable? (1 pt) 4. Provide the structure(s) of the product(s) when each of the following cation is generated in the presence of Br-(2 pts). Page 2 of 2 5. Addition of HCl to 1-vinyl-1-methylcyclopentane yields 1-chloro-1,2-dimethylcyclhexane and the reaction is exergonic. (a) Write the complete stepwise reaction mechanism. Use curved arrow to show the electron flow in the mechanism and show the structures of the intermediates (clearly label all the charges if there are any) (3 pts). (b) Draw the reaction energy diagram based on your mechanism. In the diagram, label the starting materials, products, intermediates, transition states, activation energy for each step, and the overall energy difference between the starting materials and the product (3 pts). (c) Which parameter in the diagram can be used to calculate the equilibrium constant? By using which equation? (1 pts)...
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