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practice-9-key - Chemistry 3223 325a-2— Practice Exam 1...

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Unformatted text preview: Chemistry 3223 / 325a -2— Practice Exam 1. In each pair of compounds, circle the strongest acid (3 pt each). 2. For the indicated hydrogen atom, estimate the water-referenced pKa (3 pt each). Rf“ C “‘0" “f 0LL§L€ {4.11% {'14 “3"}..— TOMA R R / L : - ‘ ‘t’('* (is-2‘s two—co iii-19 ' o dew as. .HsCQD arr-3 u~é {sf—fil— 3. For each pair of structures, circle the compound that will react fastest in an 5N1 reaction (3 pt each). \LV, 4. Complete the energy v. reaction coordinate diagrams for the 5N1 and 5N2 reactions. Label them as 5N1 and 5N2. Draw structures for the intermediates and transition states indicated by the boxes. (10 pt each) ,f qurt 3 7: . _ Ir reaction coordinate Chemistry 322a I 3253 -3- Name: Practice Exam #9 1 {3.4: 5W! .. ptnma‘ tat 47;” reaction coordinate 5. Compounds 1 and 2 interconvert when treated with sodium methoxide in methanol according to the equation below. M0 NaOMe M0 H bHa MeOH H CH3 1 2 a. Name compound 1 (3 pt). E) —.. Z-r” Lt-urftrj E but arr-xCof b. Describe the relationship between compounds 1 and 2 using one word (3 pt). E .z. m t- r! fen-=6 .- g. c. What is the M3"m1 for this reaction (3 pt)? C) {WV ...,.,.c { e. The interconversion of 1 and 2 proceeds through an achiral, charged intermediate. Draw it here. Draw all of its important resonance structures. (8 pt) cl. What is the Keq for this reaction (3 pt)? Chemistry 322a / 3253 -4— Name: Practice Exam #9 6. How many signals (types of protons) do you expect in the 1H NMR Spectra of these molecules (3 pt each)? “fie CF3 H 0 N 0 0% N N HOWO <, | Y N / 0+ Ni indole caffeine 7. What integration and coupling pattern do you expect for the indicated proton (3 pt each)? Answer nH, (s)ing1et, (d)oublet, (t)rip1et, (q)uartet, (o)ther/ complicated. Assume that the integrations are normalized accurately to count all of the hydrogens in the molecule. The first is done for you. CI Cl Chemistry 3223 / 325a -5- Name: Practice Exam #9 8. Circle the structure that best fits the illustrated 1H NMR spectrum. (10 pt) 2H 11 10 9 8 7 6 5 4 3 2 1 0 HSP-OO-3SB ppm 10 9 8 7 6 5 4 3 2 1 O HPH-IJIJ-IJBB ppm Chemistry 3223 f 3253 —(r Name: Practice Exam #9 10. A compound of the formula C7H7Cl has the 1H NMR spectrum below. Propose its structure (20 pt). 10 9 8 ? 6 5 4 3 2 1 O HPfl-Dt-GZZ ppm ...
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