Problem Set 5

# C 4 h 8 g h 2 o g c 4 h 10 o g which hydration

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C 4 H 8 ( g ) + H 2 O ( g ) C 4 H 10 O ( g ) Which hydration reaction is faster and why? (c) Draw reaction free energy diagrams on the same scale for hydration reactions of these two alkenes, showing relative free energies of both starting materials and rate-determining transition states. reaction coordinate Free Energy B (1-butene) (d) Assume that the rate-determining step of this hydration reaction is the protonation of the alkene double bond by H 3 O + . Write an appropriate rate equation for this reaction. (e) If the concentration of the alkene is doubled at parity of other conditions, what happens to the rate of product formation? (f) If the concentrations of alkene and H 3 O + are each doubled, how much faster will the reaction run? (g) Assume equal concentrations of the two alkenes exist in a flask and the acid catalyst is added. How much faster is the initial forward reaction rate of 2-methylpropylene compared to 1-butene? Chem 33, Kanan & Stack, 2012, PS 5; pg 6

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6. An intramolecular reaction is often dramatically faster than an analogous intermolecular reaction. Consider the two exergonic (irreversible) reactions below and the associated rate constants: O 2 N O O O O O O O O 2 N O O 2 N O O O O O 2 N O O O O (1) (2) P P B A C k' = 0.8 s -1 k = 4 x10 -6 M -1 s -1 If [ A ] = 1 M, what would [ B ] have to equal in order for reaction (1) to proceed as rapidly as reaction (2) when [ C ] = 1 M? Is this concentration possible? Chem 33, Kanan & Stack, 2012, PS 5; pg 7
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