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Chemistry 130B Second Hour Exam May 24 2001 1 2 3 4 5 6 8 20 50 12 10 10 Name Key Signature Total 110 Circle the Name of your TA ID On my honor I have neither given nor received aid on this exam Colleen Chris Jeremy 1 a Name the following by either a systematic or a common name Make sure stereochemistry is named if relevant The second compound is in the standard Fischer projection CHO HO H N H CH2OH Pyrrole L glyceraldehyde b Write structures for the following compounds piperidine hydroquinone OH N H OH Page 2 of 8 2 Give products of the following reactions or reaction sequences a NH2 OH 1 H3O NaNO2 excess 2 H2O NH2 OH b OCH3 OCH3 OCH3 OCH3 Br Br NO2 Br2 FeBr3 NO2 NO2 NO2 very little Br c OH Br N HO Ts d CH2I2 Zn Cu e CH3 2N 1 H2O2 2 PdOAc2 Base PPh3 Polar Solvent N Ts Page 3 of 8 3 Show how the following compounds could be easily prepared from the indicated starting materials and any additional needed reagents More than one step may be required Partial credit will be given so be sure you write out things you are sure of a NH2 Br H2N HNO3 H2SO4 Hot conc Fe HCl NO2 O2N NO2 Br O2N H2N b N HNO3 H2SO4 NO2 1 LAH 2 CH3I excess CN 1 Fe HCl 2 HNO2 H 3 CuCN continued N H N H Page 4 of 8 c O I HNO3 H2SO4 2 Fe HCl 3 HNO2 1 NaOH 2 Br N2 OH H2O d O O 1 HCN 2 LAH HNO2 CH2NH2 OH Page 5 of 8 e AlCl3 O Zn HCl Cl O Page 6 of 8 4 Provide structures for each of the capital letters in the following scheme H HO HO H CHO OH H H OH CH2OH HNO3 heat H2 Pt Br2 H2O CaCO3 C A H HO HO H CH2OH OH H H OH CH2OH B H HO HO H CO2H OH H H OH CH2OH H HO HO H CO2H OH H H OH CO2H Page 7 of 8 5 2 O fucosyllactose is an oligosaccharide found in human milk and believed to have immunostimulating effects Answer the following questions pertaining to 2 Ofucosyllactose OH OH OH O 2 HO O HO O 1 H3C O 3 OH OH O OH HO OH 2 O fucosyllactose a Is 2 O fucosyllactose a reducing or non reducing sugar Reducing b Clearly circle all anomeric carbons in 2 O fucosyllactose c Name the type and number the glycosidic bond



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