Tutorial 4 answers - Chemistry 2OA3 Nov. 9, 2010 Tutorial 4...

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Chemistry 2OA3 Nov. 9, 2010 Tutorial 4 1. (a) This is a tricky question, but makes use of all the reactions you have learned with alkenes (hydration, hydroboration, elimination, addition, etc.). The big problem is to find a series of reactions that will allow one alcohol isomer to be converted into another. You will need to use alkene intermediates to get there. For each chiral molecule, assign R or S to any chiral centres. NOTE: there may be more than one answer. For each reaction, you only need to draw one isomer. However, indicate if the reaction will produce more than one product. H 2 SO 4 /H 2 O Dilute H 2 SO 4 /H 2 O Dilute H 2 SO 4 , conc hot conc
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(b) Now do it all over again in the reverse order. 2. What is the structure of the compound of formula C 7 H 7 OBr, that has the following spectra? 1 H NMR BLOW UP 13 C NMR (ignore peak at 77 ppm: due to CDCl 3 ) 2H 2H 3H Br Br Br Br , THF
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Structure is: O Br There are many ways to work this out. E.g.: IHD = 4 (always do this first!) There is a 3H singlet at a shift of about 4: must be a Me group next to O, i.e. MeO
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Tutorial 4 answers - Chemistry 2OA3 Nov. 9, 2010 Tutorial 4...

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