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
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1 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 5 V Total 10 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. ndividual point values are given in the corner of each answer space. The exam has 6 pages in addition to this cover page. A pka table is on the last page.
2 ame. ( points) Page 1 Each of the reactions yields a PAR of main organic products, but you should only draw one. Then answer the other questions about the starting material and the products formed. A. starting material l / (i) (ii) heated P (iii) (iv) (v) Provide the complete name (including stereochemical labels as needed) for this starting material (vi) Fill in the predicted number of MR signals expected for the starting material: 1 -MR starting material KMn (i) (ii) Pd (iii) (iv) (v) Provide the complete name (including stereochemical labels as needed) for this starting material (vi) Fill in the predicted number of MR signals expected for the starting material: 1 -MR
3 . (7 points) ame Page election is everywhere. Each of the following transformations exhibits some kind of selection. Provide the required missing materials, either starting materials, products, or complete transformations. A. (i) Draw the alkene starting material s one product (i) Draw one product (ii) This product forms: with with alone (ii) This product forms:. a Despite containing two potential leaving groups, the reaction shown below yields one organic elimination product. Explain this regioselection by showing the conformation (chair) of the starting material that undergoes this E reaction; draw the product, too. with with alone (i) chair conformation favored for E reaction (ii) kinetically favored product Br Br a E D. The following transformation occur in three steps, starting with the formation of an iodonium ion intermediate and ending with deprotonation, yielding a neutral organic product. gnoring stereochemistry, draw a complete curved arrow mechanism for the formation of this product. (i) how the curved arrow mechanism for the first step (ii) Draw all products and show the curved arrow mechanism for the second step (iii) Draw all products and show the curved arrow mechanism for the third step B 10
4 ame. ( points) Page ne starting material undergoes two different transformations in each of these problems. Please draw all main organic products, clearly showing in your drawing all structural and/or stereochemical information as needed; restrict your answers to major regioisomers when regioselection is predicted, assume no rearrangement occurs, and ignore all reaction byproducts unless instructed otherwise. A. (a) Draw product(s) (b) Draw product(s) (+) α-phellandrene a flavoring Pd/ excess 1) ) Zn excess (a) Balance your reactions 1) a ) l 1) l (b) Balance your reactions l ). (a) Draw product(s) (b) Draw 8 1 product(s) Br Br heat (a) Draw product(s) 1) B (b) Draw product(s) ) /a l carene the pungent odor of turpentine
5 V. (5 points) ame Page A. upply the missing information. f any reaction yields more than one product, draw one and write "+ enantiomer" or "+ diastereomer" in the box. f you are supplying reagents and a multistep transformation is required, be sure to number your steps appropriately. equivalents of this product form 1 -MR shows signals Pd/Ba Pb Zn draw each product in the appropriate box 1 -MR shows signals. 5 l only this product is formed draw all products l 1 equivalent 1) a 1 equivalent ) D. Br + / /Pt
6 V. ( points) A. Analyze the compounds shown below. ame Page 5 ompound 1 ompound This drawing represents (fill in a number for each box) This drawing represents (fill in a number for each box) distinct molecule(s) distinct molecule(s) chiral molecule(s) When ompound 1 is treated with mildly acidic conditions, a single molecular rearrangement step results in the dehydration product, ompound. how the complete multi-step mechanism for the formation of. You should show and use the best resonance contributor for any intermediate in your mechanism. hoose your acid/conjugate base wisely. gnore stereochemistry. chiral molecule(s) ompound 1 ompound. Under these same conditions, another dehydration product is also formed, again explained by a single rearrangement step. Predict the structure of ompound 18 ompound, a structural isomer of ompound ompound 1
7 AD (trongest Acid) l l F pk a JUGATE BAE (Weakest Base) -1 l -7. l -.6 F AD l l l pk a JUGATE BAE l l l (Weakest Acid) 9 (trongest Base)
I. (32 points) Name. Page 1. (ii) its diastereomer its structural isomer its enantiomer. The product you have drawn will. H 3 CO Cl form with H 3 CO
ame. ( points) Page Each of the reactions yields a PAR of main organic products, but you should only draw one. Then answer the other questions about the starting and the products formed. Check boxes are
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
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
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
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
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:
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
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
HO HO. 1) BH 3 HCl. + enantiomer either one may be drawn 4. + enantiomer either one may be drawn 4 1) O 3
. (0 points) Page 1 A. Reaction analysis: provide the requested information in each of the following chemical transformations. how all missing starting materials and products unless otherwise indicated,
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
If Compound 2 (below) was used in the above reaction, how might things change? Name Page 1. I. (23 points)
I. (2 points) ame Page itrogen atoms in amines can undergo substitution reactions repeatedly under mildly basic conditions. Provide the structure of the starting amine and supply the missing reagent(s).
O N N. electrons in ring
ame I. ( points) Page 1 A. The compound shown below is a commonly prescribed antifungal drug. It belongs to a category of compounds known as triazoles. Analyze the geometry and other properties for various
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
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
C sp2 trigonal planar trigonal planar 3
I. ( points) ame Page A. Rocuronium bromide (Zemuron) is a muscle relaxant that is used in the application of anesthesia. It is used most often to facilitate endotracheal intubation because of its powerful
I. (42 points) (a) Label the indicated sites (circles and oval box) with the appropriate stereochemical designation.
I. ( points) ame Page A. etamethasone is a powerful anti-inflammatory drug that comes with unfortunate immunosupressive properties. It is often prescribed as a topical cream that can be used to alleviate
diene. If stereoisomeric mixtures form, indicate by drawing one and writing "+ enantiomer" and/or "+ diastereomer" in the box.
I. (9 points) Page A. Consider how varying the conditions of a reaction can vastly influence the rate of a reaction as well as the product(s) formed. First draw the product(s) that form in the reference
stereoselection view Product 1 with its enantiomer
. ( points) A. Complete the following reactions as directed. (a) Cl C1 C i) major product DBU C C C C C Page 1 ii) Draw a ewman Projection for the conformation of the C1-C bond indicated that specifically
180 C 2 -C 3 bond rotation
I. ( points) Valnoctamides have been used as sedatives and inducers for hypnosis for decades. The most biologically active molecule from this class of compounds is shown. Using ewman projections, analyze
"Pip tazo" is a nickname given to a popular combination of antibiotics prescribed for a variety of infections. A.
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HO 1:1 1:1. Amines, like cathine, are often excellent nucleophiles Provide the requested information for the following one-step reaction scheme.
I. (4 points) A. athine (shown at right) is a psychoactive amphetamine drug obtained from the plant atha edulis (also known as khat). View down the 1 - bond indicated ( 1 being the front atom), and answer
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NAME (Print): SIGNATURE: hemistry 310M/318M Dr. ent Iverson 2nd Midterm November 1, 2007 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,
"Pip tazo" is a nickname given to a popular combination of antibiotics prescribed for a variety of infections. A.
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You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
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