pset5 - Massachusetts Institute of Technology 5.13, Fall...

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Massachusetts Institute of Technology 5.13, Fall 2006 Problem Set #5 Due: November 3, 2006, 12:00 PM 1. Explain the fact that the amines shown below have considerably different basicities despite obvious similarities in structure. A B C N N N p K a NH + 5.20 7.79 10.95 2. Give the organic product(s) expected when p -chloroaniline reacts with: a) dilute HBr b) C 2 H 5 MgBr c) NaNO 2 , HCl, 0 o C d) p -toluenesulfonyl chloride 3. Give the organic product(s) expected when the product of #2c reacts with: a) H 3 O + /H 2 O b) CuBr c) H 3 PO 2 d) CuCN 4. Explain the following observation. The diazotization of 2,4-cyclopentadien-1- amine give a diazonium salt, which, unlike most aliphatic diazonium ions, is relatively stable and does not decompose to a carbocation. 5. Provide a mechanism for each for the following transformations. Ph H N O O Ph KH D , benzene KOH, H 2 O Ph NH 2 + Ph O O O H 3 C OH C CH 3 C NH 2 CH 3 CH 3 NaNO 2 , HCl H 2 O H 3 C O C C CH 3 CH 3 CH 3 1
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Massachusetts Institute of Technology 5.13, Fall 2006 6. The following syntheses are proposed for the following amines. In each case,
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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pset5 - Massachusetts Institute of Technology 5.13, Fall...

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