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Name ___________________ Section ___________________

Chem 237 Exam 2 February 24, 2012


Instructions: You will have 50 minutes to complete as many problems as possible. Where provided, write your answers in the boxes. Your answers will not be graded unless they are in the proper box.

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

2. Draw the following compounds from their names. 6 pts. a. (R)-4-methylpent-4-en-2-ol

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.

Are these products enantiomers, diastereomers, or neither?

Are these products enantiomers, diastereomers, or neither?

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?

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