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1.  For the given skeletal and condensed structures below, draw a valid line-bond structure,
with the following conditions:  
 The neutral structures (a and b) should have no formal charges.  
 Show all atoms, including hydrogens.  
 Be sure to include all lone pairs. 
 Write the hybridization and bond angle of each carbon atom. 
 Angles do not need to be drawn accurately. 
  
a. CH3CHCHCHO 
 
 
 
 
 
 
b. CH3CH2COCH3 
 
 
 
 
 
 
c.  

 
 
 
 
 
 
d.  

 
 
 
 
 
  
2. Draw in all implied hydrogens and lone pairs in the skeletal structures below, then
draw all additional resonance structures for each that do not have more formal
charges than the original structures. Use curved arrows to show the flow of electrons from
one structure to the next. 
  
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3.  Consider the following three neutral molecules with no formal charges:  
 

 
a. Draw in all lone pairs of electrons and circle the most acidic hydrogen in each of the
above molecules. 
b. Draw the conjugate base of each of the above molecules, showing all lone
pairs and formal charges. Label them clearly CB1, CB2, and CB3. If any conjugate base has
multiple resonance structures, draw all important resonance structures, using curved
arrows to show the flow of electrons from one resonance structure to the next.  
  
 
 
 

 
 
 
 
 
 
c. For the conjugate base(s) above that have non-equivalent resonance structures, circle
the major resonance structure for that molecule.  
d. Which conjugate base is the most stable? Briefly explain, comparing it to both of the
other molecules. Your explanation should take into account the structure and potential
energy of all three conjugate bases.     
 
 
 
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e. Of the original compounds 1, 2, and 3, which requires the least energy to remove a

proton? Briefly explain, referring to your explanations of stability in part d. 
 
 
 
f. Of compounds 1, 2, and 3, which is the strongest acid? Which is the weakest acid? 
 
 
  
g. Of compounds 1, 2, and 3, which would you predict has the highest pKa? The lowest? 
 
 
  
h. Of the three conjugate bases CB1, CB2, and CB3, which is the strongest base? Which is
the weakest base? 
 
 
 
  
4.  For the following disubstituted cyclohexanes: 
 Draw the two possible chair-flipped conformations. C-H bonds are not necessary. Be
sure to draw the opposite chair for your flipped structure, with no rotations.  
 Label each of the substituents axial (a) or equatorial (e). 
 Circle the conformation that is more stable (or indicate if they are equal in energy). 
  
a.    cis-1-ethyl-3-methylcyclohexane 
 
 
 
 
 
 
b.    cis-1-bromo-2-methylcyclohexane 
 
 
 
 
 
 
c.    trans-1-ethyl-3-isopropylcyclohexane