Q1_________(- points) Q2_________(- points) Q3_________(-- points) Q4_________(-- points) Q5_________(-- points) Q6_________(-- points)
Only use the front side of each page for your answers. Nothing on the back sides will be graded. If you write the exam in pencil or erasable pen, you give up your right to any kind of regrade.
1. Amine Basicity (5 points). Place the following compounds in order of their basicity with #1 being the most basic and #4 being the least basic. Work carefully. There will be no partial credit or regrades on this problem.
2. Functional Group Preparations (15 points). Give chemical equations for five methods for synthesizing 2-methyl-1-propanamine in a single synthetic step, not counting any workups.
3. Reactions of Amines (15 points). Draw the organic products of the following reactions. Indicate stereochemistry where appropriate. A reasonable answer may be “ No Reaction.”
4. Reactions of Carbonyl Compounds (15 points) Draw the organic products of the following reactions. Indicate stereochemistry where appropriate. A reasonable answer may be “ No Reaction.:
5. Reaction Mechanisms (20 points, maximum). Draw reasonable mechanisms for the reactions below. Do 2 of 3 and clearly indicate which parts you want graded. Note that Part A is worth 6 points, Part B is worth 8 points and Part C is worth 12 points.
Standard weak base aldol condensation
Dieckmann cyclization using a cyclic ester as one component
Robinson type annulation mechanism – intramolecular acid catalyzed aldol followed by acidcatalyzed dehydration.
6. Synthesis (30 points, maximum) Show how you would accomplish the following conversions. Do two of the three and clearly indicate which parts you want graded. Note that Part A is worth 5 points and part B is worth 10 points and Part C is worth 20 points....