Test 1 O Chem 2536 Spring 2005 Table of Reagents 1) KMnO4 2) H3O+ MnO2 Name_______________________________ Pledge: I have neither given nor received information on this test _________________________________ 1) Sn, HCl 2) -OH NaNO2, HCl, 0ºC 1) Provide the mechanism and product for the nucleophilic aromatic substitution shown below. Show four resonance structures for the anionic intermediate. Label the nucleophile, leaving group, and rate determining (slow) step. (13 pt) O CCH2CH3 Br Na+ -OH 1 2) Propose a mechanism to show the formation of the following product from the given reagents. (9 pt) CH2CH2CH2CHCH2-Cl AlCl3 CH 3 CH3 CH3 3) Circle the aromatic compounds. (4 pt) N NH 2 4) a. From the given structures, circle the compound that corresponds to the infrared spectrum. b. For the infrared spectrum, label the absorptions indicated in the blanks provided. (13 pt) O O OH O CCH3 CH3CCH2CCH3 CH CNCH CH3 3 3 CH3 4000 3450 3000 2000 1700 Wavenumbers (cm-1) 1000 600 ____________________ ________...