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WI04 MT1 Key - 9 NAME la(6 pts In the boxes provided draw a...

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Unformatted text preview: 9'-.. NAME: la. (6 pts) In the boxes provided, draw a valid Lewis structure for compounds I and II shown below: CH3OCH2CHCH2 [NH3CH2CH3]Br 1b. 1c. 1d. 1e. 1f. I II (2 pts) What is the hybridization for the oxygen atom in I? 5'0 3 (2 pt) What is the hybridization for the nitrogen atom in II? 5P3 (1 pt) Which of the two compounds has a higher degree of unsaturation? J: (2 pt) Which compound would you expect to be a stronger Bronsted/Lowry acid? It. (6 pts) Now provide a clear three-dimensional (3—D) structure for I and II in the boxes provided: NAME: 1g. (6 pts) In the boxes below draw both a constitutional (or itructural) isomer of I as a Lewis structure (you need not show it in 3-D), and draw a confo mational isomer of II (obviously it must be shown in 3—D; do not use a Newman projection . 1h. (5 pts) In the box below draw a Newman projection for the most stable conformational isomer of 11, viewed down the nitrogen to carbon bond. The Mflw $you/ W06 2a. 2b. 2c. 2d. NAME: (4 pts) Draw a single Lewis structure for each of the following molecules. Be sure that the structures you draw correspond to the major resonance structures. Use lines for covalent bonds and show all nonbonding valence shell electrons and formal charges. You need not show a 3—D structure. (a) CH3 NO2 ,H %/0' H i \,o'- H “e: (4 pts) Draw a 3—D structure for each of the molecules in HLM/o: l7 r? @\o ~Q I! (b) HCONH2 I t D: H—AL 53’” I‘l’£\ IV/ ”H \ H (6 pts) Protonation of acetic acid gives a structure with the formula CH3CO2 H2 + .Draw a Lewis structure for each of the two possible protonation products of formula CH3 CO2 H2+ (i. e. protonation may occur at two different sites in aceti¢ isomers is more stable and why? N ' N "rH H-lc—'C"‘O\ h 1‘ :9 H U .6 H :69' H1: ~dn9’e/7H Qua-Mina) acid). Wh1ch g the two Hiflig/‘l I H‘f" §@ (6 pts) fiive the Lewis structures for all possible constitutional (structural) 1somers of C3H80 (you need not show the structures in 3- -:D) Ho'(9':H” ,H 3“ fl .. H~<;—"*Cl1~‘-:"H ”“ffi.~f~ooflfl H H H H {T H ("“1 :1H H~§~9 are g H H H flint, 3a. 3b. NAME: (12 pts) For each of the following one—step transformations, use curved-arrow notation (electron pushing) to show the movement of electrons. Show all formal charges. b) CI HEW? —-> ‘ \AI/CI : AI ‘ / H/ CI/ \Cl Hg?) (90' v H C) H 14 fl q H E' ”W” + -"r: —-—> HAW + HBr H ’H Hi—I H H H d) E.) $H3 9H3 :NEC: + /C\@ _. ‘C/C\CH3 H CH3 .Né/ H (2 pts) Which of the transfromations in part 3a are involved in Bronsted/Lowry acid/base reactions? 6L (2 pts) Which of the transformations in part 3a would belclassified as Lewis acid/base reactions? 62 , 14, c2 W0“? ITLWI up c NAME:_______________.__.___ 3c. (6 pts) Predict the major product(s) for each of the following reactions. Write “N0 REACTION" where appropriate. H’C\C/ \H hV H H/ \H b) H H \ / excess 02 H30\C/C\C/CH3 ,. H/ \H H/ \H heat ‘7 CD; +’ ((3 H070 0) H\ / I H30 C CH3 2 \/C\/ \/c\/ h {[90 RXM H H H H V 3d. ( 6 pts ) For each of the following molecules indicate the shape (geometry) of the molecule (consider only the positions of atoms) as one of the following: tetrahedral, trigonal planar, trigonal pyramidal, bent, or linear. st BE “7' b) BH3 Mia. #4004? b) ° CH3 (a methyl radical) . d) NH: Tqfi TMflf/flrgd w 1(9- {’L/MM e) HZCO 0 C52 L-I ’V 54/ 4a. 4b. NAME: (4 pts) Circle the functional groups found in the molec le shown beloyv and name each of them. ‘ J:— ql The reaction coordinate diagram shown below corresponds to one of the propagation steps in the free radical bromination of propane. The energy level for propane and a bromine atom is indicated in the diagram. Two other energy levels, indicated by A and B, are also shown to indicate the species formed from two competing reactions that occur in this propagation step. i) (6 pts) In the boxes labelled and A and B, draw the structures of the species which are formed. Progress of Reaction 4c. 4d. NAME: ii) (1 pts) Is this step in the mechanism endothermic or exothermic? Qwoflfiml( iii) (1 pts) Is the formation of A or B faster? 8 iv) (6 pts) Indicate on the reaction coordinate diagram the activation energy for formation of A and B by using the designations AE and BEa, respectively. Why is BEa smaller than AEa? (2 pts) Briefly explain why is acetic acid a much stronger acid than a typical alcohol, such as ethanol. You will need to draw structures to make your arguments clearly and concisely. fle}d E $4.45 2%0’ DIM 07F (C3149 1? base >50; aciHc, «eta 144% Ap‘l fly Mei/co 49 (2143 «go <"> CH3“ ((5 :5. CH3 ~06) (2 pts) Draw a Molecular Orbital Energy Diagram to show the relative energies of the .717- system in ethene (CHZCHZ). Label the orbitals as bonding and antibonding and draw a picture that depicts the shape of each molecular orbital (include the sign of the wave function). You need not show the sigma energy levels. I5 ~——— rm" % ”WWW”? ...
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