1CHM 2212-Organic Chemistry II Name________________________(1)February 22, 2002Dr. BauschQuiz #6 (25 points)(covering material thru section 14.13)1. (6) Draw the various resonance structures for the intermediate carbocation ("arenium ion") formed in the bromination of benzene. There are three total resonance structures.2. (6) Indicate whether the following structures are aromatic according to the Hückel rule. You must explain your answer.+OON H23. (6) Draw the major organic product for the following reactions.+CH3CH2Cl+HNO3DH2SO4AlCl3+Cl2Fe4. (6) Note the following transformation:+C4H7OCl1) AlCl32) H2OAC10H12OBOn the following two pages are the 13C and 1H NMR spectra of the product B.Deduce the structure of both B and A.313C spectrum of product (C10H12O)two signals here!490 MHz 1H NMR spectrumof product (C10H12O)multiplet (5H)triplet (2H)sextet (2H)triplet (3H)The multiplicity and integration values are given below the
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