Professional Documents
Culture Documents
Problem 1 2 3 4 5 6 7 8 9 10
Points ____/8 ____/6 ____/18 ____/12 ____/12 ____/12 ____/9 ____/10 ____/9 ____/8
Total
____/100
Name ___________________ Section ___________________ 1. For each of the following reactions, draw the key intermediate you would expect and the major product. 8 pts
b. (Z)-3-cyclohexyl-5-fluoropent-2-ene
c. (2E,4Z)-2,4-octadiene
Name ___________________ Section ___________________ 3. Fill in the boxes with the appropriate reagents and/or products. When a product is asked for, draw the major product only. Include stereochemistry where appropriate. 18 pts
Name ___________________ Section ___________________ 4. Draw both stereoisomers that you would expect to get from the following reactions: 12 pts.
5. Propose a synthesis of the following molecule from any alkane (C and H atoms only). Draw all reagents and intermediates. 12 pts
Name ___________________ Section ___________________ 6. For each of the following pairs of molecules, identify them as enantiomers (E), diastereomers (D), or neither (N). Circle all chiral compounds. 12 pts
7. Cholesterol(drawn below) is a major component of your cell membranes. 9 pts a. Identify all chirality centers in the molecule with arrows. b. How many total stereoisomers are there?
Name ___________________ Section ___________________ 8. Draw an arrow pushing mechanism to explain the formation of these two hydration products. 10 pts
9. Ozonolysis of an unknown compound A gives just one product. If you hydrogenate A, it reacts with 2 moles of hydrogen for every mole of A and gives you a 1:1 mixture of two isomeric products. Draw a structure for A and draw its hydrogenation products. 9 pts
Name ___________________ Section ___________________ 10. A space alien has given you a sample of an unknown compound. The alien says that it is an 80:20 mixture of enantiomers. You measure its rotation to be +18o. What would be the rotation of a pure sample of the major enantiomer? (8 pts) The alien gives you another sample and you measure its rotation to be -15o. What is the enantiomeric excess? What is the ratio of enantiomers?
Invert sugar is a 50:50 mixture of fructose and glucose. Fructose has a rotation of -100o. Glucose has a rotation of +50o. What is the rotation of invert sugar?
High fructose corn syrup is also a mixture of fructose and glucose. You are given a sample of high fructose corn syrup with a rotation of 0o. What is the ratio of fructose to glucose?