1 of 9 Third Midterm Exam [Chapters 8-10 (Carey textbook)] CHE201A-C Professor Diver and Dr. Clizbe Nov. 21, 2014 Fall 2014 Version B (Exam duration: 1 h 30 min) NAME:______________________________________________ circle one: Dr. Clizbe or Dr. Diver and: Section ( A, B, C ) TA Name:____________________________ or CHE203 Page Total Possible Points (Possible Points per page) Points 2 25 3 20 4 15 5 30 6 30 7 20 8 15 9 Periodic Table TOTAL POSSIBLE: 150 YOUR TOTAL:_________ Molecular models are ALLOWED; calculators are NOT ALLOWED. No cell phones or extra paper will be provided. Fill out the exam in pen, use the back of the page if more room is needed. CHECK THAT ALL YOUR EXAM INCLUDES ALL 9 PAGES.2 of 9 1. (30 pts) Circle the correct structure for each question. (5 points each). (a) Which of the following dienes will not react the in the Diels-Alder reaction? (b) Which of the following nucleophiles is the strongest? (c) Which is the most reactive dienophile? (d) Which of the following molecules cannot be made by acid-catalyzed hydration of an alkyne? (e) Which of the following will have the fastest rate in an SN2 reaction? OONCBrSOOOOOOO OOBrBrBrBr3 of 9 (f) Which of the following molecules represent an allylic halide? (circle all that apply) 2. In the following hydration of butyne, compound A is initially formed, but was not isolated. Draw the final isolated product (compound B) and use the arrow formalism to show electron movement to provide a detailed mechanism showing each individual step going from compound A to compound B (15 points). BrBrCH2ClCH2Cl4 of 9 Molecular Orbital Theory 3. (15 points) Answer the following questions based on 1,3-butadiene. (5 points each) (a) Draw the HOMO. (b) Draw the LUMO. (c) Draw the transition of the reaction between 1,3-butadiene and ethylene.5 of 9 4. (30 points) For the following reactions indicate if the mechanism goes by SN2, SN1, E2 and/or E1. Give only the product(s) for the major pathway. If more than one product is formed from the same pathway, state which product is major. Show stereochemistry where applicable. (6 points each). (a) (b) (c) (d) (e) OTsNaN3Mechanism type: __________BrCH3KCNDMFMechanism type: __________6 of 9 5. (30 points) Write the major organic product for each of the following reactions. Provide stereochemistry where applicable. (6 points each) (a) (b) (c) (d) (e) CNNC+1. NaNH2, NH32. CH3Br3. H2, Pd, CaCO3 lead acetate, quinoline1.2.SOOCl, pyridineCH3CH2CH2COHCH3CNa7 of 9 6. Reaction Mechanism (20 points) * Using the arrow formalism to show electron movement, provide a detailed mechanism showing each individual step of the reaction mechanism. Be sure each step is charge balanced and mass balanced. For full credit you must account for the use of all reagents and explain the formation of both products in the reaction. * Circle the major product. 1 equiv. HBrheatBr+Br8 of 9 7. Synthetic Pathway Show how the following conversion can be accomplished in good yield. More than one step will be needed. Provide the reagent(s) needed for each step. Also, include the product of each step. (Mechanism, transition states, mechanistic intermediates are not needed) (15 points) HO9 of 9 Fr87francium223.01973 45678 9 101112Cs55cesium132.9054Rb37rubidium85.4678K19potassium39.0983Na11sodium22.9897Li3lithium6.941H1hydrogen1.00794226.0254Ba56barium137.327Sr38strontium87.67Ca20calcium40.078Mg12magnesium24.3056Be4berylium9.01218Ac59227.0278La57138.9055Y3985.4678Sc2144.9559Raradium58104724022TiV Cr Mn Fe Co Ni Cu Zn23 24 25 26 27 28 29 30scandiumtitanium vanadium chromiummanganeseiron cobalt nickelcopperzinc47.88 50.9415 51.9961 54.9381 55.847 58.933254.6963.546 65.39ZrNb Mo Tc Ru Rh Pd Ag Cd41 42 43 44 45 46 47 48zirconiummolybdenumtechnetium ruthenium rhodiumpalladiumsilver cadmium91.244 92.9064 95.94 98.9063 101.07 102.9055 106.42 107.8682 112.411HfTa W ReOsIr Pt AuHg73 74 75 76 77 78 79 80hafnium tantalum tungstenrheniumosmium iridium platinumgoldmercury178.49 180.9479 183.85 186.207 190.2 192.22 195.08 196.96654 200.59niobiumyttriumlanthanumB C N O F Ne5 6 7 8910boron carbon nitrogenoxygen fluorineneon10.811 12.011 14.00674 15.9994 18.9984032 20.1797Al Si P S Cl Ar13 14 15 161718aluminumsiliconphosphorussulfur chlorineargon26.981539 28.0855 30.97376 32.066 35.4527 39.948Ga Ge As Se Br Kr31 32 33 343536galiumgermanium arsenicselenium brominekrypton69.723 72.61 74.92159 78.96 79.904 83.80InSn Sb Te I Xe49 50 51 525354indiumtinantimonytellurium iodinexenon114.82 118.71 121.75 127.6 126.904 131.29Tl Pb Bi Po At Rn81 82 83 848586thallium lead bismuthpolonium astatineradon204.3833 207.6 208.9804 208.98 209.987 222.0176He2helium4.002602actiniumTh90thorium232.0381Ce58cerium140.115Pa91231.0359Pr59140.907659260Nd PmSmEuGdTbDyHo Er61 62 63 64 65 66 67 6 8praseodymiumneodymiumpromethiumsamariumeuropiumgadoliniumterbiumdysprosiumerbium144.24 146.9151 150.36 151.965 157.25 158.925 162.50 164.930 167.26UNpPu AmCmBkCfEs Fm93 94 95 96 97 98 99 100uraniumplutoniumamericium curium berkelium californium einsteinium fermium238.0289 237.0482 244.0642 243.0614 247.0703 247.0743 251.0796 252.0829 257.0951neptuniumprotactiniumTm Yb69 70thuliumytterbium168.9342 173.04Md No101 102mendelevium nobelium258.0986 259.1009Lu71lutecium174.967Lr103lawrencium260.1053Ac89227.0278La57137.9055lanthanumactiniumholoniumThe Periodic Table of the ElementsIIIA IVA VA VIA