EXAM 1 Review Questions

1. (4 pts) Draw structures corresponding to these names.

a) 2,2-diphenylhexane b) meta-nitrobenzoic acid
 
 
 
 

7. (3 pts) Rank the compounds below in order of their reactivity to electrophilic aromatic substitution. Label the most reactive "1" and the least reactive "4". Place the numbers in the blanks under the compounds.

8. (9 pts) Circle or fill in the requested information for each of the following structures.

a) Continuous cyclic pi system? Yes / No

   # of pi electrons

  Circle one: Aromatic / Not Aromatic

b) Continuous cyclic pi system? Yes / No

# of pi electrons         Circle one: Aromatic / Not Aromatic

c) Continuous cyclic pi system? Yes / No

# of pi electrons         Circle one: Aromatic / Not Aromatic

9. (6 pts) Below is shown a reaction used in an attempt to synthesize cycloheptatrienyl bromide. The product isolated had the correct molecular formula, but did not behave as expected. The product was a high melting solid (203o with decomposition) that was not soluble in organic solvents, but was soluble in water. Propose a structure that would rationalize these results and explain the basis for the compound not having the cycloheptatrienyl bromide structure.

10. Give the major organic products for each of the following reactions. Indicate stereochemistry for each reaction marked with an asterisk (*). If no reaction is predicted, write NR. (15 pts)
 
 

a)

b)

c)*

d)

e)


 
 

 11. Choose the best reagents from the list below for effecting the following conversions. Place the letter of the reagents of your choice in the blank to the left of the conversionn. (12 pts) A. 1. CH3CH2Cl, AlCl3

     2. KMnO4, H2O

     3. HNO3, H2SO4

B. 1. CH3CH2CH2Cl, AlCl3

     2. Br2, FeBr3

C. 1. CH3Cl, AlCl3

     2. HNO3, H2SO4

     3. KMnO4, H2O

D. 1. Cl2, FeCl3

      2. KMnO4, H2O

     3. HNO3, H2SO4

E. 1. CH3CH2COCl, AlCl3

     2. H2, Pd

     3. Br2, FeBr3

F. 1. HNO3, H2SO4

     2. CH3Cl, AlCl3

     3. KMnO4, H2O

G. 1. KMnO4, H2O

     2. Cl2, FeCl3

     3. HNO3, H2SO4

H. 1. CH3CH2COCl, AlCl3

     2. Br2, FeBr3

     3. H2, Pd
    1. 1. HNO3, H2SO4
2. Cl2, FeCl3

3. KMnO4, H2O

 a)________

b)________

c)________

12. (6 pts) Write the three resonance structures expected for the initial intermediate expected from the following reaction.

13. (2 pts) Which structure (A or B) above is:

    1. the nucleophile?
    2. the electrophile?
14. Starting with benzene, synthesize the following compound. Show all reagents and all intermediate compounds in the synthetic sequence. (6 pts) HINT: Three steps are required.