tut6 - eq at 400 K(c Sketch an energy diagram for the...

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1 CHM 138H TUTORIAL 6 As described in the course outline, the tutorial quizzes will be based closely upon the textbook questions recommended below for this week's tutorial as well as those recommended in last week's tutorial. You should be able to do the questions below from the course textbook (J. McMurry, 7 th Edition). Please work through them in preparation for Tutorial 6. Chapter 5: 5.1, 5.4, 5.6-5.13, 5.17-5.21, 5.30, 5.31, 5.34-5.41. Of the above, the following represent some of the better questions: 5.8, 5.9, 5.20, 5.30, 5.31, 5.37, 5.38, 5.39, 5.40, 5.41. In addition, the following problem will be discussed: 1. When the following alkene is reacted under aqueous acidic conditions at room temperature, isomerization occurs via a carbocation intermediate to generate a different alkene product. H 3 O + + + H 3 O + (a) State the type of isomerism exhibited by the two alkenes in this equilibrium. (b) G o for this reaction is -2.8 kJ/mol. Calculate K
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Unformatted text preview: eq at 400 K. (c) Sketch an energy diagram for the reaction, labeling any known energy changes and the location of transition states and/or intermediates. (d) Write a complete, detailed mechanism for the reaction, using curved arrows to represent electron flow. Note that water is present as well as H 3 O + under aqueous acidic conditions, and that the acid is catalytic in this reaction. (e) The trisubstituted alkene formed in this reaction can further react with HBr to form a tertiary cycloalkyl bromide as the major product. Write a mechanism for this transformation, using curved arrows to represent electron flow. 2 Here are some good Flashware animations to take a look at from Chapter 5: Arrow Pushing: nucleophiles/electrophiles Arrow Pushing: form/break C-X sigma bond Arrow Pushing: form/break C-X + sigma bond Arrow Pushing: nucleophilic substitution (Nu-+ R-L) Arrow Pushing: nucleophilic substitution (Nu + R-L + )...
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This note was uploaded on 05/09/2010 for the course CHEMISTRY 138 taught by Professor Dicks during the Spring '10 term at University of Toronto.

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tut6 - eq at 400 K(c Sketch an energy diagram for the...

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