1. (15 points) Write a complete IUPAC name for each of the following compounds, including designation of stereochemistry if it is specifically shown:
a) 
b) 
c) 
2. (15 points) Complete each of the following reactions by adding the missing part: either the starting compound, the necessary reagents and conditions, or the final major product. Indicate stereochemistry if it is specific.
a) 
b) 
c) 
d) 
e) 
3. (10 points) The structure of D-fructose is shown below in a Fischer projection.
How many stereocenters are in this molecule ?
How many stereoisomers of D-fructose are there ?
How many of these stereoisomers are meso compounds ?
How many of these stereoisomers are diastereomers of D-fructose ?
What is the relationship of D-fructose to the other stereoisomers (the ones that aren't diasteromers) ?
4. (15 points) The pKa of CH3OH2+ is - 2.2 .
Write out the specific reaction that this refers to.
Write the Ka in terms of concentrations.
Knowing this pKa value, predict the preferred direction of the following equilibria:
5. (15 points) Write all the steps in the complete mechanism for the addition of HBr to 1-methylcyclohexene. Show electron-pushing arrows. Predict which is likely to be the rate-determining step.
6. (15 points) Addition of HCl to 3-methyl-1-butene gives the expected Markovnikov product, but also gives some 2-chloro-2-methylbutane.
Explain by writing a complete mechanism that shows how both products could be formed.
7. (15 points) Hydroxide ion could react with acetaldehyde (shown below) in two different ways.
Clearly show electron-pushing arrows to illustrate what happens in each reaction.
Describe each reaction type (i.e. , what has happened?)
(A) -
(B) -
Assume both reactions are favorable, and B is more favorable than A, yet A is a faster reaction than B. Draw an approximate potential energy diagram that would be consistent with this.
