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CHEM2320:                                                                                         2007-2008
Practice Test #2: Chapters 4 & 5                                                                  Version 1

Classify each reaction below as a(n):
addition
elimination
substitution
rearrangement

Place the letter corresponding to the correct answer in the blank to the left of the reaction.(1 point each)




_______________




_______________




_______________


Identify and label the nucleophile and electrophile in each reaction below. (2 points each)
Add curved arrows to the following reactions to indicate the flow of electrons in each. (5 points each)




Drawing
There are 11 constitutional isomers for cycloalkanes with the formula C6H12. Draw 8 of them. (8 points)




6. For each substituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation.
Indicate how much more stable (KJ/mol) the more stable conformation is relative to the less stable
conformation. (5 points each)
Naming
7. Write a correct IUPAC name for the following compounds. (2 points each (16))
                  CH3
                               CH3
                                  CH3
H3C

                               CH3
   H3 C

                 CH3



           CH3

                         CH3


H3C
      Cl
                 CH3

                   CH3

                 CH3




                   Cl




                  Br




           I




           F
Structures
Draw Structures of the following molecules. (2 points each (14))

1,1-dimethylcyclohexane




2-cyclopropyl-4-methylpentane




cis-1,2-dimethylcyclohexane




2,4-dimethylhexane




3,4-dichlorohexane




1,1-dichloro-3-sec-butylheptane




1-bromo-5-chloro-3-cyclopropyloctane




Reaction Energy Diagram

Draw a reaction energy diagram for a exergonic reaction with two intermediates. Intermediate A is higher in energy than intermediate
B and the rate of first step is the slowest rate. Label all important stages of this reaction and all appropriate energies.

				
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