Exam 2 w'09

Exam 2 w'09 - CHEM 312 Exam 2 Winter 2009 The Gardening...

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CHEM 312 Exam 2 Winter 2009 The Gardening Exam NAME Page Points 1 /18 2 /17 3 /25 4 /25 5 /18 6 /36 7 /11 TOTAL /150
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For this exam, we’re going to look at chemicals used in gardening as the medium by which you get to show me all you’ve learned. 1. (18 points total) Let’s start by clearing the plot of land. You could weed everything by hand, or you could kill the plants chemically. Let’s go with chemical treatment. A natural herbicide is D-limonene, shown below: a. (4) Limonene is isolated from orange peels by steam distillation. Limonene is a chiral molecule. Draw the enantiomer in the space above. b. (4) Limonene is a terpene. Circle the isoprene units in the structure above. c. (4) If D-limonene has an optical rotation of +96˚, what is the optical rotation of a 80:20 mixture of D:L limonene? d. (6) Show the product of complete hydrogenation of D-limonene by completing the reaction below. How many chiral centers does the new product have? How many stereoisomers are possible? + H 2 Pd Total, page 2
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2. (17 points total) Well, limonene isn’t all that great of an herbicide, so you go back with something more effective, propanil, shown below. N
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Exam 2 w'09 - CHEM 312 Exam 2 Winter 2009 The Gardening...

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