INSTITUTE OF CHEMISTRY College of Science University of the Philippines Diliman, Quezon City 1101

CHEMISTRY 101.2, 2nd sem, AY 2013-14 Guide Questions

I. Organic Chemistry Experiments 1. Total Synthesis a. Show the stepwise reaction mechanisms of each product. b. Each product is used as a dye for a specific clothing material. What materials correspond to each product? Show the interactions between the clothing material and the product? c. What salient features must the infrared spectra of the products show to qualitatively show the completion of the reactions for each step? 2. Polymer Synthesis a. Show the stepwise reaction mechanisms of each product. 3. Diels Alder a. Explain the effect of varying solvents on the percent yield of the Diels-Alder reaction of isoprene and methyl acrylate. b. What are the advantages and disadvantages of using polar and non-polar solvents in Diels-Alder reaction? c. What salient features must the infrared spectra of the products show to qualitatively show the completion of the reactions for each step? 4. Photochemical Synthesis a. Outline reaction mechanisms for the transformations from benzophenone to benzopinacol to benzopinacolone. What is the major reason for exposure of the mixture of benzophenone and isopropyl alcohol (with acid) to direct sunlight? Would the reaction work if the Erlenmeyer flask had been coated with sunscreen? b. Pinacol (2,3-dimethyl-2,3-butanediol) gives a mixture of pinacolone (3,3-dimethyl-2-butanone) and 2,3-dimethyl-1,3-butadiene on treatment with acid. Outline reasonable mechanisms for the formation of each of these products. c. What are the uses and applications of pinacol and benzopinacol? Of pinacolone and benzopinacolone? d. What is a Jablonski diagram? How is it used in photochemical phenomena? e. Explain the difference between phosphorescence and fluorescence. f. What salient features must the infrared spectra of the products show to qualitatively show the completion of the reactions for each step? g. What type/mode of excitation does benzophenone undergo for it to react? Explain using the correct mechanism for the photochemical reaction.

II. Analytical Chemistry Experiments 1. AAS a. What is the effect of the added KCl in the analysis of Ca in terms of its action as ionization suppressor? b. What is the effect of adding PO43- ions in the absorbance of Ca?
c. What is the purpose of adding Lanthanum in the analysis of Ca? How does it affect the absorbance of Ca in the presence of PO43- ions?

d. Why is there a need to ash the milk sample at 550C, and subsequently treating it with 10% HCl? e. What will be the effect on the absorbance if the solvent used is 20% propanol in water instead pure water? 2. Spectrotitration 3. HPLC 4. GC (FR) a. What types of samples are analyzed by the GC technique without difficulty? b. List at least 3 common GC detectors and applicable samples. c. Differentiate between isocratic and temperature programming. d. Compare and contrast the use of manual injection and Head Space auto-injector. What are the advantages of using Head Space auto-injector? e. List at least 3 common stationary phases and applicable samples. f. GC peaks are easily influenced by a variety of instrumental factors. These are compensated by using the internal standard method. In this method, a uniform amount of internal standard is added to the mixture containing known amounts of the analyte and to the samples of unknown analyte concentration. The ratio of the peak height (or peak area) for the analyte to that of the internal standard is calculated. The table lists the data obtained from a GC expt.
% analyte 0.05 0.10 0.15 0.20 0.25 unknown Peak height analyte 18.8 48.1 63.4 63.2 93.6 58.9 Peak height internal std 50.0 64.1 55.1 42.7 53.8 49.4

Use the excel program to answer the questions. Construct a spread sheet to determine the height ratio of the analyte to the internal standard and plot this vs. the analyte concentration. Determine the concentration of the unknown and its standard deviation. 5. Voltamm 6. ISE a. What are the advantages of potentiometric methods? b. Why must the ISE be polished before taking potential readings? c. What is the significance of sonicating the toothpaste sample? d. Compare and contrast the two methods used for the analysis of fluoride in the sample. e. Discuss the possible sources of error and how these will affect the calculated values.