NAME _____________________      Chem 311 002     Quiz 3      Fall 2001

 

1. Name/Draw the following:

     a.  3-methyl-4-isopropyl-5-tert-butyldecane        b.  bicyclo[3.2.1]nonane

 

 

 

 

 

c. _______________ d. _________________ e. _______________________

 

2.  The boiling points increase with ( increased, decreased ) molecular weight by
  
____degrees/CH2 group.  Increased branching in similar MW isomers
    ( increases, decreases ) boiling point. Explain this last statement.

 

3.  Draw all 8 structural  isomers of pentyl group and name 4 of them.

 

 

 

 

 

 

 

 

4.  Draw the sawhorse and Newman projections and clearly indicate the dihedral
    angles of the most stable conformer of butane.

 

 

 

 

 

 

5.  Write three completely balanced reactions of cyclobutane using one mole of
  
reactant:

      A.

 

      B.

 

     C. 

 


6.  Complete the following combustion data table and fill in each line:

                            Total
  
               Heat Combust.   __________            __________       Strain Energy

cyclopropane  499 kcal/mole  166 kcal/mole          9.2 kcal/mole     27.6 kcal/mole

 

Cyclobutane          655.9               ___                  ___                  ___

 

cyclohexane           944                 ___                  ___                  ___

 

linear alkanes                               ___                  ___                  ___

 

7.  Include the name of the fraction and the use for each bp range alkane

     b.p. range               # C=s                fraction                         Use

     <30o C                   2-4       __________________       _________________

   30-180                    4-9       __________________       _________________

   160-230                  8-16     ___________________     __________________

   200-300                 10-18               diesel fuel                     motor fuel

 

8. Which of the following cycloalkanes are capable of (cis-trans) isomerism? Draw
    the cis and trans isomers.

        a. 3-ethyl-1,1-dimethylcyclohexane        b. 1,4-dimethylcyclohexane

 

   

 

        c. 1-ethyl-3-methylcyclopentane         d. 1-cylopropyl-2-methylcyclohexane

 

 

 

 

9. Draw the two conformers of trans-1-methyl-2-t-butylcyclohexane and indicate
    the most stable conformer. Explain your answer.

 

 

 

 

 

 

10.  Explain why the 1,3-diaxial interactions are so important in determining the
    most stable conformers in substituted cyclohexanes.