130AL FINAL EXAM
WINTER 1999

CONDENSED ANSWER KEY
1. 110 °C (±10)
2. ligroin, tetraphenylcyclopentadienone, benzil, dibenzyl ketone
3.
 
4. Anhydrous Na2SO4 has a higher capacity because it will complex more water
than anhydrous MgSO4.
5.
 
+3 points for arrow pushing for each step; + 2 points for equilibrium arrows;
-1 point for each wrong charge assignment; ­ 6 points for wrong alcohol or
carboxylic acid (or for not defining "R" group).

6. a) efficient extraction of excess acetic acid

b) extracts isopentyl alcohol
c) neutralizes reaction (kills catalysis)

(not necessary to show for full credit)
7.
a) 

b)

c)

8. NaBH4 is less reactive and thus more easily handled.  LiAlH4 reacts
violently with protic solvents such as water or alcohols. NaBH4 is stable
in water.
9. time required for a compound to come off the column; decrease; decrease; decrease
10. 3, 6, 11, 4
11.
 
 
unsaturated stretch or =C­H stretch 3007.5 cm-1

      saturated stretch or ­C­H stretch 2960, 2871 cm-1

      O=C­O­C=O anti-symmetric stretch 1866 cm-1

      O=C­O­C=O symmetric stretch 1785 cm-1

      C=C stretch (very weak) 
 12. 
 

      


      
+15 points
(or any aryl R group variation)

      
 

      
+3 points