Chemistry 130B Second Hour Exam May 24, 2001 1 8 Name: Key 2 20 3 50 ID: 4 12 On my honor, I have neither given nor received aid on this exam 5 10 6 10 Signature: Total 110 Circle the Name of your TA: 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. NH CHO2OHHHOCH Pyrrole L-glyceraldehyde b. Write structures for the following compounds piperidine hydroquinone NH OHOHPage 2 of 8 2. Give products of the following reactions or reaction sequences. a. NH2NH21.H3O+/NaNO2, excess2. H2OOHOH b. OCH3NO2Br2/FeBr3OCH3NO2BrOCH3NO2BrOCH3NO2Br+very little c. BrNTsHOPdOAc2Base, PPh3Polar SolventNTsOH d. CH2I2/Zn(Cu) e. (CH3)2N1.H2O22. ∆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. BrBrNO2O2NH2NNHNH2H2NNHNO2O2NHNO3/H2SO4Hot, conc.Fe/HCl b. NO2CNN+HNO3/H2SO41. Fe/HCl2. HNO2/H+3. CuCN1. LAH2. CH3I (excess) (continued)Page 4 of 8 c. N2+H2OOOHBrI. HNO3/H2SO42. Fe/HCl3. HNO21.NaOH2. d. OHCH2NH2OHNO2O1. HCN2. LAHPage 5 of 8 e. OClOZn/HClAlCl3Page 6 of 8 4. Provide structures for each of the capital letters in the following scheme. CHOHOHHHOHHOOHHCH2OHABCH2OHHOHHHOHHOOHHCH2OHCO2HHOHHHOHHOOHHCH2OHCCO2HHOHHOHHOOHHCO2HH2/PtHNO3heatBr2, H2OCaCO3HPage 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-O-fucosyllactose. OOHHOOHOHOOOHOHOHOOOHHOOHH3C2-O-fucosyllactose123 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 between monosaccharides 1 and 2. alpha 1,2 bond d) Is monosaccharide 2 a D or L sugar? DPage 8 of 8 6. Special problem. This problem has very little credit and could be very time-consuming. You should probably try it only after you have finished everything else. Attempts to carry out Hofmann elimination on the compound shown below instead lead to the carboxylate shown. Give a mechanism for this reaction and its conditions. OCO2–Hofmann