ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 7, Problem 59P

Consider the following S N 1 reaction.

Chapter 7, Problem 59P, Consider the following SN1 reaction.  a.Draw a mechanism for this reaction using curved arrows.

a. Draw a mechanism for this reaction using curved arrows.

b. Draw an energy diagram. Label the axes, the reactants, products, E a , and Δ H ο . Assume that the starting material and product are equal in energy.

c. Draw the structure of any transition states.

d. What is the rate equation for this reaction?

e. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from I to Cl ; [2] The solvent is changed from H 2 O to DMF; [3] The alkyl halide is changed from ( CH 3 ) 2 C ( I ) CH 2 CH 3 to ( CH 3 ) 2 CHCH ( I ) CH 3 ; [4] The concentration of H 2 O is increased by a factor of five; and [5] The concentrations of both the alkyl halide and H 2 O are increased by a factor of five.

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2. The bromination of 2-butene is an exergonic reaction. Br H3C. Br2 CH3 CH3 Br a. Draw the mechanism for the reaction (you may ignore the stereochemistry for this question). b. In the mechanism drawn above, identify any intermediates. C. How many transition states are involved in the above mechanism? Without drawing the transition state(s), indicate where they occur in the mechanism. d. Which of the following reaction co-ordinate diagrams best illustrates this reaction? Explain briefly. On the diagram, draw the structures of the reactants, products and intermediates at the correct locations on the diagram and indicate which position(s) correspond to the transition state(s). Page 18 of 19 EYRERIMENT 7: BROMINATION OF CINNAMIC ACID WINTER 2022
:Draw two major products :Reaction type for the major product :Draw one minor product :Reaction type for the minor product
Draw all products that are formed during the 3 reaction steps.

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ORGANIC CHEMISTRY

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