PracticeProblemsII - 1 Practice Problems II CHM 242 Prof...

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1 Practice Problems II CHM 242 Prof. Shin Fall 2015 1. Draw the mechanisms and energy diagrams showing intermediates(s) for the reactions of t -butyl chloride with sodium ethoxide in ethanol (E2) and t -butyl chloride with sodium hydroxide in water (E1). Put both reactions on the same energy diagram below. CH 3 H 3 C CH 3 Cl + NaOEt EtOH E2 CH 3 H 3 C CH 3 Cl + NaOEt H 2 O E1 Energy Reaction Coordinate
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2 2.a. When t -butyl bromide undergoes solvolysis (reaction with the solvent) in a mixture of CH 3 OH and H 2 O solvent, the rate of solvolysis increases when the percentage of H 2 O is increased. Explain and draw the reaction mechanism. Draw all intermediates/transition states, charges, and arrows . (Hint: think about the mechanism and kinetics and the difference between water and methanol to assist/stabilize mechanism.) 2.b. Draw an energy diagram of the reaction and label the products, reactants, and transition states or intermediates. Indicate relative energies. 3. A mixture of approximately 30% cis- and 70% trans -1-chloro-1,2-dimethyl cyclopentane (where the methyls on the same side are considered to be cis ) is formed if the pure trans isomer is allowed to stand at 20°C.
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