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14C_w11_finalB - Chemistry 14C Winter 2011 Final Exam Part...

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Chemistry 14C Winter 2011 Final Exam Part B Page 1 Page 1 score = You may be familiar with a test that law enforcement officers can use to determine if an unknown substance is an illicit drug. In this test the unknown substance is mixed with ninhydrin. If a pale red color develops then the unknown is assumed to be an illegal drug such as MDMA ("ecstasy"). The reaction depends on the presence of R 2 NH in the unknown. (Drugs with RNH 2 such as methamphetamine give an intense blue color.) Questions 1–14 refer to these molecules. O O OH OH + O O N CH 3 O O H N H CH 3 Ninhydrin (colorless) MDMA (colorless) Test reaction product (red) 1. (3) List all of the functional groups present in ninhydrin. 2. (7) Draw in the boxes two additional, significant resonance contributors for MDMA. Include formal charges and lone pairs for contributors in the boxes. Write “most significant” below the most significant contributor. O O HN CH 3 3. (2) Write a number in the blank. Ignoring what is beyond , __________________ atoms of the test reaction product are conjugated. 4. (6) Complete this sentence by adding thirty words or less : Ninhydrin and MDMA are colorless whereas the test reaction product is red because... 5. (2) Which ring(s) of the test reaction product are aromatic (circle one): Five-membered ring Six-membered ring Both rings Neither ring Their aromaticity cannot be considered separately 6. (4) Write one number in each blank. Ninhydrin has ___________________ stereocenters. Including the
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