Friday Session 1 - A loses its proton more slowly than...

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Chem 3580 Spring 2010 Friday Session - Week #1 1. Label each of the structures below either as aromatic, antiaromatic or nonaromatic. Rationalize your answers. (Note that assumptions, such as planarity, in Q1 of Problem Set #1 have been removed. You must determine whether or not a structure could be planar and what the consequences are likely to be.) N H O + O N H B CH 3 2. The structures shown below have been made and characterized by 1 H NMR spectroscopy. The numbers beside the hydrogen atoms of the rings denote the chemical shifts in the 1 H NMR spectrum of each species. The chemical shift for the hydrogen atoms of benzene is approximately δ = 7.3 ppm. Designate each structure as aromatic, nonaromatic or antiaromatic. Give reasons for your answers. N ! 4.93 H H H H H H ! = 2.07 ! = 3.65 H H ! = 5.3 ! = 5.6 H ! = 6.73 ! = 6.73 ! = 6.62 ! 4.93 3. Compound
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Unformatted text preview: A loses its proton more slowly than compound B . Explain. Use chemical structures to clarify your reasons. H CN Ph Ph A H CN Ph Ph B 4. Phenylpropanoic chloride, C 6 H 5 CH 2 CH 2 COCl, react with AlCl 3 to give a single product with the formula C 9 H 8 O and an 1 H NMR spectrum with signals at = 2.53 (triplet, J = 8 Hz, 2H), 3.02 (triplet, J = 8 Hz, 2H), and 7.2-7.7 (multiples, 4 H). Propose a structure for the product and suggest a mechanism for its formation. 5. Suggest a mechanism for the reaction shown below that accounts for the indicated stereochemical result. H HO CH 3 O H CH 3 1. AlCl 3 2. H 3 O + + 6. Write a stepwise mechanism for the following reaction. Use curve arrows to show the flow of electrons in each step. + 1. AlCl 3 2. H 3 O + CH 2 Cl 2...
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This note was uploaded on 02/16/2010 for the course CHEM ORGANIC CH taught by Professor Dotsevisogah during the Spring '09 term at Cornell University (Engineering School).

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