UCI DEPARTMENT OF ORGANIC CHEMISTRY PEER TUTORING REVIEW SESSION FEEDBACK EVALUATION Quarter: Fall Date: 12/7/18 Class: Rychnovsky Final Review Tutors Names: Ying Chow, Hannah Nguyen, Joshua Torosyan COMMENTS/ SUGGESTIONS (VERY IMPORTANT!) Ying Chow: Hannah Nguyen: Joshua Torosyan: What worked best? What could be improved? What would you like to see next time? This review was interactive and engaging. Comments The presentation volume was acceptable. Comments Strongly Disagree Disagree Neither Agree or Disagree Agree Strongly Agree The presentation was visually clear and logically organized. Comments The review improved/reinforced your understanding of the material. Comments The quality of the review packet was excellent. Comments Please fill out this evaluation, even if you plan to leave early. Thank you very much.
This page is intentionally left blank on purpose. You can use this page as scratch work if you want.
Organic Chemistry Peer Tutoring Department University of California, Irvine Ying Chow (chowyl@uci.edu) Hannah Nguyen (hannahln@uci.edu) Joshua Torosyan ( torosyaj@uci.edu) Chem 51A Professor Rychnovsky http://sites.eee.uci.edu/ochemtutors 1. [M + H] + formulas and masses C6H9N2O: 125.1405 C7H9O2: 125.1427 C7H13N2: 125.1836 C9H17: 125.2233 Final Review a. Given the m/z ratio of 125.1430 an unknown protonated compound, what is the molecular formula of the unknown compound? b. Calculate the unsaturation number of this compound. c. Using the following IR spectrum and H NMR spectrum, draw a possible structure to this unknown compound.
2. a. What does H NMR measure? What does C NMR measure? b. How many H NMR signals will this compound have? c. How many C NMR signals will this compound have? d. Which of these H NMR signals will be the most downfield? Why? e. Which of these H NMR signals will be the most upfield? Why? f. Which of the bonds in compound would have the highest frequency in an IR spectrum? Why?
3. Cocaine (Methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclooctane-2-carboxylate) acts by inhibiting the reuptake of serotonin, norepinephrine, and dopamine. There is a marked stereoselectivity in the psychomotor stimulant effects of cocaine; this stereoselectivity does not carry over to the toxic effects of cocaine. The specific rotation of or Cocaine is shown below. a. Label each stereocenter as R or S. b. How many stereoisomers would this compound have? c. Label each functional group. d. A sample of cocaine with a concentration of (3.5 g cocaine /50 ml ethanol) using a 3 dm cell. Calculate the observed rotation of the sample. e. Given that the specific rotation of D-cocaine is -38 what is the % ee of the cocaine sample from part a? f. How many grams of each enantiomer of Cocaine are present in the sample?
g. If this Cocaine sample was mixed with 125 ml of orange juice, what would the concentration of the sample be? h. Using the concentration from part g for part a, calculate the measured rotation of the sample. 4. Rank the following in order of increasing boiling points (1 lowest - 3 highest). a. b.
5. Determine whether each compound is achiral, chiral, or meso. Label each stereocenter as R or S. State the relationship between the two compounds.
9. For the given molecule, draw all resonance structures, include formal charge, and determine which one is the most favorable. 10. a.) Convert the following molecule into three variations of the staggered Newman Projection at C3 and C4. Determine the most stable conformation. b.) Convert the following chair molecule into a Newman Projection. Assume that there are only C-H bonds present.
11. Convert the following Newman Projection into both chair conformations. Determine which one is favored at equilibrium. 12. Determine the type of acid-base reaction being conducted. Show arrow pushing and determine the final product. Label formal charges, if any. Specify the nucleophile and electrophile. 13. Determine the type of acid-base reaction being conducted. Show arrow pushing and determine the final product. Label formal charges, if any. Specify the nucleophile and electrophile, along with the acid and base. Determine which side equilibrium will favor.
14. Using the following H NMR spectra, match the compounds to the correct H NMR spectrum. a. b. c. d.