Consider the following SN2 reaction: Br + CN CN + Br acetone a. Draw a mechanism using curved arrows. b. Draw an energy diagram. Label the axes, the reactants, products, Ea, and AH°. Assume that the reaction is exothermic. c. Draw the structure of the transition state. d. What is the rate equation? e. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from Br to I; (2] The solvent is changed from acetone to CH,CH,OH; [3] The alkyl halide is changed from CH3(CH2),Br to CH,CH,CH,CH(Br)CH; [4] The concentration of "CN is increased by a factor of five; and [5] The concentrations of both the alkyl halide and "CN are increased by a factor of five.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 18CTQ
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Consider the following SN2 reaction:
Br
+ CN
CN
+ Br
acetone
a. Draw a mechanism using curved arrows.
b. Draw an energy diagram. Label the axes, the reactants, products, Ea, and AH°. Assume that the reaction is exothermic.
c. Draw the structure of the transition state.
d. What is the rate equation?
e. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from Br
to I; (2] The solvent is changed from acetone to CH,CH,OH; [3] The alkyl halide is changed from CH3(CH2),Br to
CH,CH,CH,CH(Br)CH; [4] The concentration of "CN is increased by a factor of five; and [5] The concentrations
of both the alkyl halide and "CN are increased by a factor of five.
Transcribed Image Text:Consider the following SN2 reaction: Br + CN CN + Br acetone a. Draw a mechanism using curved arrows. b. Draw an energy diagram. Label the axes, the reactants, products, Ea, and AH°. Assume that the reaction is exothermic. c. Draw the structure of the transition state. d. What is the rate equation? e. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from Br to I; (2] The solvent is changed from acetone to CH,CH,OH; [3] The alkyl halide is changed from CH3(CH2),Br to CH,CH,CH,CH(Br)CH; [4] The concentration of "CN is increased by a factor of five; and [5] The concentrations of both the alkyl halide and "CN are increased by a factor of five.
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