Level 2 – TLC Calculations The following is a standard phase TLC chromatogram. Calculate the Rf of the most polar eluting compound using the following chromatogram and ruler. Use the lines provided to the right of each spot in your calculations. Select the closest possible answer.    

Level 1 – H-NMR How many signal envionrments would N,N-diethylamine show in its 1H-NMR spectrum?

Level 1 – Extractions, Stoichiometry, and Solution Chemistry – The Classic Carbonate Example  Balance the following acid/base extraction equation: __a_ Na2CO3 (aq)  + __b___ RCOOH (aq)   ↔ ___c__ RCOO- (aq) + ____d___ Na+ (aq)   +  ___e____ H2CO3 (aq)  ↔  __f____ CO2 (g) +  ____g___ H2O (l)   (Answer Pattern: a:b    c:d:e      f:g)

Level 4 – H-NMR to Spectra Matching   The spectra above contains integration data provided above the peaks (e.g. 2H = integration of 2) What molecule best matches the spectra above?Note: This is a real spectra, so some signals may overlap. Use integration appropriately.

Level 1 – UV Spectroscopy Which of the following compounds does not exhibit fluorescence when exposed to UV light?

Level 1 – Predicting Splitting Patterns of C-NMR When considering 3-hexanone, predict the splitting pattern of the carbonyl.

Level 1 – Mass Spectroscopy – Isotopic Ratios A student is examining a mass spectrum and has observed an m/z peak at 222 and 224 in a ratio of 3:1. What functional group is most likely present?

Level 3 – Sterochemistry of SN1/E1 Reactions After reacting n-butyl alcohol with HCl, the expected major product is expected to be ___________.

Level 3 – Response/Correction Factors and Gas Chromatograpy Data A student performs a gas chromatography experiment similar to the one used in lab. They are attempting to determine the appropriate correction factor for Unknown 2. What is the corrected area for Unknown 1 if Compound A’s correction factor is set to 1.00? Assume that Standards A–D are reference standards (white background), and Unknowns 1–3 represent components of an unknown sample (grey background). Given: Compound Standard A Standard B Standard C Standard D Unknown 1 Unknown 2 Unknown 3 Elution time (s) 75    100 120  160 102 123 163 Area (mV*s) 880 1110 1180 1360 1340 990 1080 Correction Factor A (1) B C D E F G  

Level 2 – SN1, E1, SN2, E2  We’ve covered the essentials for SN1, SN2, and E1 reactions and determining how a set of reaction conditions will proceed involves ranking 3 factors: 1) The nucleophile/base2) The leaving group3) The solvent Focusing on these 3 factors, and recalling what we’ve discussed in the slides, which of the following is true?