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1 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 Total 0 omplete Lewis structures are required unless you are given other specific instructions. Precision in drawing counts. heck all three-dimensional representations to ensure you are implying an unequivocal direction of bonding. 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 pka table is on the last page.

2 I. ( points) ame Page 1 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 neuromuscular blocking effect. (a) Label the indicated chiral stereocenters with the appropriate stereochemical designation. 1 + Br - 1 (b) For each of the atoms indicated with an arrow, provide the atom's most reasonable hybridization as well as its electronic (VEPR) geometry, and its observable geometry (shape). Atom ybridization 1 Electronic (VEPR) geom. bs. geom (shape) B. Each of the following transformations yields one major organic product (i.e., no mixtures of stereoisomers or regioisomers). Draw this product for each (do not worry about byproducts, focus on the product that is being synthesized). Please pay close attention to the direction of each arrow. 1) Br /FeBr 1) K ) (cat.) ) K Br a Br (cat.)

3 II. ( points) ame Page A. For each of the compounds shown below: (1) Identify any sources of stereochemistry by circling the site(s) and providing appropriate stereolabel(s) for each site. If no stereochemistry is present, write "E." () Then choose the statements (A-F) that can be used to describe that molecule and write the letters in the box under each molecule. If no descriptions apply, write "E" in the smaller box. Identify and label any source(s) of stereochemistry 1 Identify and label any source(s) of stereochemistry A) is a meso compound B) has at least one chiral diastereomer ) has an enantiomer D) has at least one achiral diastereomer E) has a meso stereoisomer F) would show < 1 -MR signals Identify and label any source(s) of stereochemistry Identify and label any source(s) of stereochemistry B. For each of the following pairs, choose all the descriptions (A-G) that apply; write the letters corresponding to those descriptions in the box with the pair of drawings. 1 1 and : A) are enantiomers B) are diastereomers ) are structural isomers D) are conformational isomers (conformers) E) are identical molecules F) contain at least one R stereocenter (in the pair) G) represent at least one achiral compound and : and 8: 9 and 10: 5 and 6:. Translate the molecular structure to a name and the name to a molecular structure (include stereochemistry): (i) Br (ii) ()-1-chloro--methylcyclobut-1-ene

4 III. (0 points) ame Page A. The following rearrangment reaction yields an isocyanate product that is useful in organic syntheses. It begins with a proton transfer, then a rearrangement step completes the transformation. Provide the missing information in each box. (ii)the product of this first step is best shown as a set of two resonance contributors, each containing only one charged atom: draw them. (i) Provide the curved arrow mechanism proton transfer (iii) Using the BET resonance contributor, show the curvedarrow mechanism for the formation of product set shown below. 10 (iv) Draw the other major resonance contributors for the isocyanate product + isocyanate product (v) Assuming the hybridization model for all atoms (considering all resonance contributors) provide an accurate and complete three-dimensional orbital picture for the best overall resonance contributor for the isocyanate product, using 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. 1 B. The following energy diagram reveals the energy changes that occur during a specific reaction when formation of one carbocation leads to two possible rearrangements, eventually leading to structurally isomeric products. Answer the questions about the diagram. Be sure to show the sign of all energy changes. Energy A B (i)what step is the ratedetermining step in the K to A (reverse) transformation? D E Reaction Progress I J F G K kcal/mol (ii) Which product would be favored if the reaction were run reversibly, under thermodynamic conditions? (iii) List the points that represent transition states in this diagram. (iv) Estimate the ΔG for the step with the smallest k r in the A to K (forward) transformation. (v) What is the ΔG for the ratedetermining step for the complete A to G (forward) transformation?

5 IV. ( points) A. Provide the missing information. (i) 1 ame Page (iii) Using a ewman projection, draw the most stable conformation for the 1 - bond; 1 should be in front. l / 1 l 1 (ii) alone 1 forms: with its enantiomer circle one with its diastereomer 5 When Molecule 1 is treated with a bulky base, a bimolecular elimination process yields alkene product(s). Draw all products expected to form. (iv) 1 l B. The following addition reaction yields a variety of structurally isomeric products sharing the formula Draw the other products (,, and 5), given the information provided. onnectivity alone (no stereochemistry) should be considered in your drawings. after a single rearrangement (i) without rearrangement (ii) 1 -MR: 8 signals (iii) 1 -MR: 6 signals stereoisomeric mix stereoisomeric mix single achiral molecule DBU E (cat.) 6 5 (iv) Draw the most straightforward curved arrow mechanism for the formation of 6 from, using and + as needed. This transformation requires two rearrangement steps. Ignore stereochemistry. 6 18

6 V. (1 points) ame Page 5 A. Molecule 1 undergoes bimolecular elimination to yield a single alkene product. Provide a drawing for the conformation of 1 that undergoes this elimination. As always, be sure to show both axial and equatorial positions for all substituted ring atoms. Draw bond angles carefully, and show connectivity and stereochemistry clearly. (i) hair conformation that undergoes E (ii) alkene product 1 l 6 The results of the above reaction might change if Molecule is used as the starting material instead of Molecule 1. Answer the questions to show if (and how) anything might change. l (iii) Molecule 1 and Molecule are: circle one enantiomers diastereomers structural isomers unrelated compounds (iv) Molecule will yield circle one a larger a smaller the same (v) Molecule will react circle one more slowly than faster than at the same rate as number of E products as Molecule 1 Molecule 1 B. Each of the following reactions yields two major products that share the same molecular formula. Draw these products, showing all stereochemistry (if any) clearly, and define their relationship. (i) and are: (circle one) 1) 9-BB ) /a enantiomers diastereomers structural isomers 6 (ii) 5 and 6 are: (circle one) (excess) Pd/ enantiomers diastereomers structural isomers 5 6 6

7 VI. (0 points) A. Draw a circle around the compounds which are aromatic or contain at least one aromatic ring. ame Page 6 5 B. The Pictet-pengler Reaction involves an interesting twist on EA reactions. When the starting material is placed in an acidic environment, a proton transfer generates the strong electrophile required for EA. Provide the most straightforward three-step curved arrow mechanism that leads to the product shown; the acid used to generate the electrophile is regenerated. You may use -B and B - for any proton transfer step. B. omplete the following by providing the missing information. If any product forms as a stereoisomeric mixture, please draw one structure showing stereochemistry clearly and write "+ enantiomer" or "+ diastereomer" in the box. When providing reagents, be sure to number steps and draw all appropriately. (i) equivalents 1) Pd/Ba Pb ) + B 15 KMn 1) ) /a/

8 AID (trongest Acid) l I l F pk a JUGATE BAE (Weakest Base) -1 l -7. I l -.6 F AID l l l pk a JUGATE BAE l l l (Weakest Acid) 9 (trongest Base)

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