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1 Page of 11 Chemistry 118C Final Exam June 14, 2006 Dr. Xi Chen Name___________________________________________ Last First Middle TA_____________________________________________ Page 1 This exam contains 11 pages and 9 problems. When you are told to start, check to see that all the pages are there. If not, ask for help now. No adjustments will be made later. 1. (9 pts) Name (IUPAC system) or draw the structure of each of the following compounds (3 points each). (a) Benzyl benzoate Points 2 3 4 5 6 (b) 7 CH3CH2CH2CH2 O O C CH2CHCH CH2 CH3 8 9 10 (c) O O O 11 Total 2. (8 pts) The 1H NMR chemical shifts and the carbonyl IR absorption peak of a compound (C11H14O2) are given below. Write out its structure. 1 H NMR Spectrum Doublet 1.2 (6H) Singlet 3.5 (2H) Multiplet 4.3 (1H) Multiplet 7.1 (5H) IR (C=O stretch) 1740 cm-1 Page 2 of 11 3. (33 pts) Multiple choice. Circle the correct answer. a) (3 pts) Which of the following is the strongest acid? CH3CHCH2COOH Cl Cl CH3CHCHCOOH Cl CH3COOH CH3CH2CHCOOH Cl b) (3 pts) Which of the following is the strongest acid? OH COOH CHO OH c) (3 pts) Which of the following is the C-4 isomer of D-Glucose? H H H H HO C O C OH C OH C OH C H CH2OH H HO H HO H C O C H C OH C H C OH CH2OH H H HO HO H C O C OH C H C H C OH CH2OH HO H HO H H C O C OH C H C OH C OH CH2OH d) (3 pts) Which is the least reactive towards water? O CH3CH2COCH3 O CH3CH2CN(CH3)2 O CH3CH2CCl O O CH3CH2COCCH3 e) (3 pts) Which is the least stable cation? CH2+ CH2+ CH2+ CH2+ OH F NH2 CH3 Page 3 of 11 f) (3 pts) D-Galactose and L-Galactose are Anomers Conformers Enantiomers Epimers g) (6 pts) Which one of the following represents a natural occurring amino acid. It has an ____ (R or S) configuration. It is a(n) ______(D- or L-) amino acid. H H2N C COOH CH2OH CH2SH H C NH2 COOH NH2 H C CH2(CH3)2 COOH H H2N C COOH CH2SH h) (3 pts) Which of the following is a D-ketohexose? CH2OH C OH C H C H C OH C OH H C OH C O C OH C OH CH2OH H H HO H HO C O C OH C H C OH C H CH2OH CH2OH C O H C OH HO C H H C OH CH2OH H HO HO H O H H H H i) (3 pts) Which of the reagents listed in the following can be used to distinguish between and OH Ag(NH3)2OH OH NaHCO3 NaOH/H2O Dilute HCl j) (3pts) Which one of the following is the strongest base? CH3 NO2 NO2 NO2 NO2 NH2 NH2 NH2 NH2 Page 4 of 11 4. (54 pts, 3 pts each) Write the structure of the major organic product(s) of each reaction shown below (each reaction has at least one product). If you think there will be no reaction, write "no reaction". a) 1. KMnO4, KOH, 2. H+, H2O b) Br2, cat. PBr3 CH2CO2H O c) O + Br OH H3O+ NH2 d) CH3 1. excess CH3I 2. Ag2O, H2O 3. e) CH2OH C O C H OH H C OH CH2OH excess HIO4 f) CH2OH C O H C OH H C OH CH2OH NaBH4 g) H2N CO2H H3O+ Page 5 of 11 h) CH2 CH CH2 i) O O C (CH2)16CH3 O O C (CH2)16CH3 O O C (CH2)16CH3 NaOH, H2O CH2OH C O H C OH H C OH CH2OH excess C6H5NHNH2 j) H2C CH CH2 CH CH CH CH3 CH2CH3 OH k) Concentrated HNO3 CO2CH3 l) 1. 2CH3MgBr, ether 2. H+, H2O OH m) 1. NaOH 2. CO2, 125oC, pressure 3. H+, H2O n) Product of "m" excess CH3CH2OH, H+, CH2Br o) 1. NaCN 2. LiAlH4, ether Page 6 of 11 OH O HO p) HO HO OH 5(CH3CO)2O Pyridine, 0oC, 24 h q) OH CH3 NaOH, H2O, CH3CH2Br OCH3 r) + O O O AlCl3 5. (12 pts) The pKa values for the functional groups in the amino acid lysine are: CO2H, 2.2; main chain NH3+, 9.0; side chain NH3+, 10.5. Identify the form of lysine that would predominate in aqueous solution at each of the following pH values: pH 1, pH 6, pH 9.5, and pH 12. Possible forms of lysine: +NH3 (CH2)4 + H3N C COO H pH value: NH2 NH2 + NH3 + NH3 (CH2)4 (CH2)4 + H3N C COOH H2N C COO H H (CH2)4 (CH2)4 + H3N C COOH H2N C COO H H A. (8 pts) Insert appropriate pH values in the above space (leave the space blank for a structure that does not predominate at any of the indicated pHs. B. (4 pts) (Circle the correct answer.) The isoelectric pH for lysine (pI) is: 2.2 5.6 6.4 9.0 9.8 10.5 Page 7 of 11 6. (36 pts, 12 pts each) Write out detailed, step-by-step mechanisms and the major organic product(s) for each reaction shown below. Be sure to show electron pair arrows for each step. 1. NaNH2, liquid NH3 a) O O CH3CH2OCCH2CCH3 + Br 2. H3O+ 3. Page 8 of 11 O b) CH2 CH 1. NH3, HCN 2. H3O+, 3. NaOH (Neutralization) HO c) HO OH O HO OH CH3OH, HCl Page 9 of 11 7. (24 pts, 12 pts each) Write out the detailed reaction conditions and important intermediates for the synthesis of the following molecules, using the indicated starting materials (more than one step). COO + H3N CH CH2CH2SCH3 a) Br CH(CO2C2H5)2 (Methionine) O b) CH2Br Page 10 of 11 8. (14 pts) The structure of a monosaccharide (compound 1) is shown here. HO HO OH O HO Please fill in the following blanks: (3 pts) The name of compound 1 is: ____________________________ (2 pts) The chair conformation of the anomer of compound 1 is: OH Compound 1 (3 pts) Draw the Fisher projection of compound 1: (6 pts) Write out the major products of the following reactions: Compound 1 + aqueous bromine (pH 6.0) Compound 1 + dilute HNO3 Page 11 of 11 9. (10 pts) Draw the detailed structure of a single strand RNA sequence CGUA with provided information. NH2 N O N H Cytosine (C) O NH O N H Uracil (U) N NH2 N N O NH N N H Adenine (A) N N NH2 H Guanine (G)

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