exam3gilbertkey - [12] 1. The following questions require...

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2 [12] 1. The following questions require that you provide the structure of an organic compound, which you may write using “zig-zag” representations if appropriate. You are also asked to provide other information in each question, so don’t forget to read the question carefully! (6) a. Write the structure of 3-chloro-1,2-propanediol and with an asterisk (*) specify stereocenter(s), if any, that you can identify in it. HO OH Cl * (6) b. Write the structure of an acyclic terminal alkyne of molecular formula C 5 H 6 Cl 2 that contains no stereocenters. Provide an IUPAC (systematic) name for the isomer you write. 3,3-dichloro-1-pentyne 4,4-dichloro-1-pentyne 5,5-dichloro-1-pentyne 1,5-dichloro-1-pentyne H C C C Cl Cl CH 2 CH 3 H C C CH 2 C Cl Cl CH 3 H C C CH 2 CH 2 CHCl 2 Cl C C CH 2 CH 2 CH 2 Cl H C C CHCH 2 Cl CH 2 Cl 3-chloromethyl-4-chloro-1-pentyne [25] 2. Predict the organic product(s) expected from each of the following reactions. If more than one product is predicted, circle the one you expect to be major. Using wedges and slashes, show the stereochemistry of the product if this is relevant. If racemates are expected to be formed, you need to write only a single enantiomer rather than both of them. NOTE: No mechanisms are required or desired for these questions! (5) a. C C CH 3 Br 2 (1 eq.) CH 2 Cl 2 CH 3 Br Br (3) b. C C CH 3 H 2 (2 eq.) Ni CH 3 (3) c. CH CH 2 Br Br 1. NaNH 2 (liq) (3 eq) 2. NH 4 Cl C CH (Question 2 is concluded on the next page)
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3 2. (concluded) Predict the organic product(s) expected from each of the following reactions. If more than one product is predicted, circle the one you expect to be major. Using wedges and slashes, show the stereochemistry of the product if this is relevant. If racemates are expected to be formed, you need to write only a single enantiomer rather than both of them. NOTE: No mechanisms are required or desired for these questions!
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This note was uploaded on 02/18/2010 for the course CHEMISTRY 310N taught by Professor Gilbert during the Summer '08 term at North Texas.

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exam3gilbertkey - [12] 1. The following questions require...

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