1.5 h; 100 points please print clearly Dr. Kathleen Nolta Signature UM ID # Problem Points Score GSI I 20 II 20 III 20 IV 17 V 23 Total 100
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1 hemistry 0 irst ame irst Examination Last ame. h; 00 points please print clearly Dr. athleen olta ignature UM ID # PRIT TE IRT LETTER YUR LAT AME ERE: Problem Points core GI I 0 II 0 III 0 IV 7 V Total 00 omplete Lewis structures are best. Precision in drawing counts. heck all three-dimensional representations to ensure you are implying an unequivocal direction of bonding and appropriate stereochemistry. Do not forget to include important features such as nonbonding electron pairs and formal charges when appropriate. Individual point values are given in the corner of each answer space. The exam has 6 pages in addition to this cover page. A pa table is on the last page.
2 I. (0 points) Page xamic acid is a relatively simple compound (molecular formula ), and its structure is shown below. It is a potent inhibitor of the enzyme lactate dehydrogenase, essential for the efficient metabolism of glucose in muscle tissue. Assess the structure of this molecule. (a) What is the anticipated observable geometry (shape) for this oxygen atom? (c) What is the anticipated electronic (VEPR) geometry for this carbon atom? (b) What is the anticipated hybridization for this oxygen atom? (d) What is the anticipated observable geometry (shape) for this nitrogen atom? (e) Provide an accurate and complete three-dimensional orbital picture for oxamic acid as it is shown above. You should use lines, dashes, wedges, and p orbitals (lone or overlapping) to show the direction of all electrons (or empty orbitals) in your drawing. All bond angles should reflect the appropriate geometry and hybridization chosen for your drawing. (f) Draw complete Lewis structures for two different compounds, structural isomers of oxamic acid ( ), with the criteria given (more than one answer is possible for each). (i) The first isomer - contains only closed shell, uncharged atoms - contains a -atom ring - contains no hydrogen bond donor groups. (ii) The second isomer - contains only closed shell, uncharged atoms - contains an sp hybridized nitrogen atom - contains one hydrogen bond donor group.
3 A. II. (0 points) or each pair of drawings, check all descriptions that apply. Page (i) (ii) (iii) These drawings represent (check all that apply): structural (constitutional) isomers different molecules the same molecule "unequal" resonance contributors "equal" resonance contributors an acid/base (A/A - ) pair These drawings represent (check all that apply): structural (constitutional) isomers different molecules the same molecule "unequal" resonance contributors "equal" resonance contributors an acid/base (A/A - ) pair These drawings represent (check all that apply): structural (constitutional) isomers different molecules the same molecule "unequal" resonance contributors "equal" resonance contributors an acid/base (A/A - ) pair. omplicated ring systems can sometimes be represented by large numbers of resonance contributors. The compound below is a good example of this concept: many contributors could be drawn, including the one provided. Draw only four additional all closed shell contributors in which at most only two atoms carry formal charge (+ or -). (i) ontributor (ii) ontributor (iii) ontributor (iv) ontributor 4 v) f the contributors you have drawn, which is the best and state why?
4 III. (0 points) Page A. Deoxycholic acid is a bile acid generated in the metabolism of cholic acid by intestinal bacteria. It is a natural detergent and emulsifier that dissolves fatty material. The DA approved the use of this compound (tradename ybella) as an injectable treatment for the reduction of fat deposits under the chin. (a) or each of the atoms indicated with an arrow, provide the atom's most reasonable hybridization as well as its electronic geometry (VEPR) and observable geometry (write none if it is not observable). hybridization electronic geometry observable geometry atom atom Deoxycholic acid atom atom. Deoxycholic acid is shown again below with several bonds highlighted. Answer the questions using this structure for your reference. (a) ircle the best hydrogen bond donor site(s). (a) ow many sp carbon atoms are in deoxycholic acid? (b) Rank the following bonds ( being the shortest; if any are the same length, give them the same number). carbon-oxygen bonds (c) Rank the following bonds ( being the shortest; if any are the same length, give them the same number). bonds to hydrogen (e) Is this how the molecule would look in tissue at a p of ~7? Explain your answer. (d) Rank the following bonds ( being the shortest; if any are the same length, give them the same number). carbon-carbon bonds
5 IV. (7 points) Page 4 A. onsider the reactivity of oxamic acid (remember page?). xamic acid contains two acidic protons, one with a p a ~ and the other with a p a ~. You should be able to predict the sites coordinating with these p a s based on the p a table or your familiarity with these functional groups. f the bases supplied, circle the ones that can deprotonate this compound only once with a eq > 0 4 even if an excess of base is provided. oxamic acid a r. Provide the curved arrow mechanism for the most favorable/likely reactions that would be predicted to occur with the given starting materials; then draw all product(s). In all cases, draw the best possible structure when more than one resonance contributor is possible. Draw complete Lewis structures and be sure to clearly indicate atom(s) carrying formal charge(s). (a) Use your understanding of resonance to best predict the basic site for this Lewis complexation reaction. a a (i) curved arrow mechanism (i) provide product(s); balance your reaction (b) Draw the product(s) predicted to form in this : reaction; balance your equation and provide a eq. (i) curved arrow mechanism eq = provide product(s); balance your reaction (c) Draw the two form(s) of oxamic acid that you would expect to exist in the highest concentration in a slighly acidic muscle cell at p. highest concentration lower concentration
6 V. ( points) Page Provide the missing information for each of the reactions - note that these are all simple acid/base reactions, either Lewis or ronsted. Predict the eq for each proton transfer reaction, or write /A if the reaction is not a proton transfer. In all cases, draw the best possible resonance contributor when resonance is present. ALAE YUR REATI!!! (i) l e l + l eq = (ii) + eq = (iii) Draw complete Lewis structures eq = (iv) r eq = (v) Provide the curved arrow mechanism for this transformation, catalyzed by lactate dehydrogenase. R R
7 AID (trongest Acid) l I l p a JUGATE AE (Weakest ase) - l -7. I l -4.6 AID l l l p a JUGATE AE l l l (Weakest Acid) (trongest ase)
1.5 h; 100 points please print clearly Dr. Kathleen Nolta Signature UM ID # Problem Points Score GSI I 24 II 19 III 20 IV 21 V 16 Total 100
hemistry 0 First ame First Examination Last ame.5 h; 00 points please print clearly Dr. Kathleen olta ignature UM ID # PRIT TE FIRT LETTER F YUR LAT AME ERE: Problem Points core GI I 4 II 9 III 0 IV V
1.5 h; 100 points Signature UM ID # Problem Points Score GSI I 17 II 20 III 20 IV 19 V 24 Total
hemistry 10 First ame First Examination Last ame May 0, 01 please print clearly 1.5 h; 100 points ignature UM ID # PRIT TE FIRT LETTER F YUR LAT AME ERE: Problem Points core GI I 17 II 0 III 0 IV 19 V
2.0 h; 240 points please print clearly Dr. Kathleen Nolta Signature. Problem Points Score GSI I 42 II 35 III 36 IV 46 V 42 VI 39 Total 240
hemistry 10 irst ame inal Examination Last ame.0 h; 0 points please print clearly Dr. Kathleen olta ignature UM ID # Problem Points core GI I II 5 III IV V VI 9 Total 0 Precision in drawing counts. heck
1.5 h; 120 points Signature. Problem Points Score GSI I 23 II 30 III 23 IV 24 V 20 Total 120
hemistry 0 econd Examination June, 0 First ame Last ame please print clearly.5 h; 0 points ignature For fastest return, if you are in lab this term. LAB GI: UM ID # PRIT TE FIRT LETTER F YUR LAT AME ERE:
1.5 h; 120 points please print clearly Dr. Kathleen Nolta Dr. Jordan Walk. Problem Points Score GSI I 23 II 27 III 24 IV 22 V 24 Total 120
hemistry 10 econd Examination First ame Last ame 1.5 h; 10 points please print clearly Dr. Kathleen olta Dr. Jordan Walk ignature UM ID # PRIT TE FIRT LETTER F YUR LAT AME ERE: Problem Points core GI I
2 h; 240 points please print clearly Dr. Kathleen Nolta Signature UM ID # Problem Points Score GSI I 42 II 44 III 40 IV 43 V 31 VI 40 Total 240
hemistry 10 First ame Final Examination Last ame h; 0 points please print clearly Dr. Kathleen olta ignature UM ID # PRIT TE FIRT LETTER F YUR LAT AME ERE: Problem Points core GI I II III 0 IV V 1 VI 0
2 h; 240 points Signature UM ID # Problem Points Score GSI I 42 II 45 III 35 IV 46 V 36 VI 36 Total 240
hemistry 10 First ame Final Examination Last ame June 5, 01 please print clearly h; 0 points Signature UM ID # PRIT TE FIRST LETTER F YUR LAST AME ERE: Problem Points Score GSI I II 5 III 5 IV V VI Total
1.5 h; 120 points please print clearly Dr. Kathleen Nolta Signature. Problem Points Score GSI I 20 II 27 III 25 IV 22 V 26 Total 120
hemistry 0 First ame econd Examination Last ame. h; 0 points please print clearly Dr. Kathleen olta ignature UM ID # PRIT TE FIRT LETTER F YUR LAT AME ERE: Problem Points core GI I 0 II 7 III IV V Total
Problem Points Score GSI I 30 II 21 III 28 IV 30 V 31 Total 140
hemistry 0 First ame Third Examination Last ame.5 h; 0 points please print clearly Dr. Kathleen olta ignature UM ID # PRIT TE FIRT LETTER F YUR LAT AME ERE: Problem Points core GI I 0 II III 8 IV 0 V Total
Problem Points Score GSI I 22 II 26 III 28 IV 19 V 25 Total 120
hemistry 0 First ame econd Examination Last ame.5 h; 0 points please print clearly Dr. Kathleen olta ignature UM ID # PRIT TE FIRT LETTER F YUR LAT AME ERE: Problem Points core GI I II 6 III 8 IV 9 V 5
1.5 h; 140 points please print clearly Dr. Ginger Shultz Dr. Kathleen Nolta. Problem Points Score GSI I 32 II 27 III 32 IV 25 V 24 Total 140
hemistry 10 Third Examination First ame Last ame 1.5 h; 10 points please print clearly Dr. Ginger hultz Dr. Kathleen olta ignature UM D # PRT TE FRT LETTER F YUR LAT AME ERE: Problem Points core G 7 V
ATOM O1 ATOM N2 ATOM O2 ATOM N1 ATOM N2 ATOM C
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sp 2 sp 2 trigonal planar bent 2
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O N N. electrons in ring
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