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Consider the following reaction: CH3 C H H H O H3C C H H H

Chapter 6, Problem 6.49

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QUESTION:

Consider the following reaction: CH3 C H H H O H3C C H H H O Br Br @ @ + + The following rate equation has been experimentally established for this process: Rate = k[HO-][CH3CH2Br] The energy diagram for this process is shown below: Reaction coordinate C H3C H H Br C CH3 H H HO HO + + Br Potential energy @ @ (a) Draw the curved arrows showing a mechanism for this process. (b) Identify the two characteristic arrow-pushing patterns that are required for this mechanism. (c) Would you expect this process to be exothermic or endothermic? Explain. (d) Would you expect DSsys for this process to be positive, negative, or approximately zero? (e) Is DG for this process positive or negative? (f) Would you expect an increase in temperature to have a significant impact on the position of equilibrium (equilibrium concentrations)? Explain. (g) Draw the transition state of this process and identify its location on the energy diagram. (h) Is the transition state closer in structure to the reactants or products? Explain. (i) Is the reaction first order or second order? (j) How will the rate be affected if the concentration of hydroxide is doubled? (k) Will the rate be affected by an increase in temperature?

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QUESTION:

Consider the following reaction: CH3 C H H H O H3C C H H H O Br Br @ @ + + The following rate equation has been experimentally established for this process: Rate = k[HO-][CH3CH2Br] The energy diagram for this process is shown below: Reaction coordinate C H3C H H Br C CH3 H H HO HO + + Br Potential energy @ @ (a) Draw the curved arrows showing a mechanism for this process. (b) Identify the two characteristic arrow-pushing patterns that are required for this mechanism. (c) Would you expect this process to be exothermic or endothermic? Explain. (d) Would you expect DSsys for this process to be positive, negative, or approximately zero? (e) Is DG for this process positive or negative? (f) Would you expect an increase in temperature to have a significant impact on the position of equilibrium (equilibrium concentrations)? Explain. (g) Draw the transition state of this process and identify its location on the energy diagram. (h) Is the transition state closer in structure to the reactants or products? Explain. (i) Is the reaction first order or second order? (j) How will the rate be affected if the concentration of hydroxide is doubled? (k) Will the rate be affected by an increase in temperature?

ANSWER:

Step 1 of 13

(a)  In this process, a hydroxide anion attacks a carbon to make a new C-O bond while breaking the C-Br bond to release a bromide ion at the same time.

This can be shown by drawing an arrow from the oxygen of the hydroxide to the carbon to show the forming bond as well as an arrow from the C-Br bond to the bromine atom to show the breaking bond.

     

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