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F07 final key - Student 1D u Circle your TA’s name Danny...

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Unformatted text preview: Student 1D# u , Circle your TA’s name: Danny José CHEM 30A Winter 2006 Final Exam March 21, 2006 REAQ Tflls FIRSTlll!!! The exam consists of 13 questions on 14 pages. For all questions, show your work and give the answers to the correct number of significant figures and units. Chemical names must be spelled correctly for full credit. Be sure to state any assumptions! You must show your work, and it must be legible for you to receive credit. Indicate clearly if your work continues onto the back of a page! You must have your answers written in blue or black ink it you want a regrade. Please sign the honor statement below before beginning. The answers in this examination booklet are entirely my own work. I neither gave nor received information or assistance in writing this examination. I understand that sharing information during this examination, or using materials not explicitly allowed by the instructor, will result in a failing grade on this exam, and possibly in additional action that may affect my ability to continue attending UCLA. SIGNATURE R: 8.314J-K-‘moi‘1 R = 0.0821 L-atm - moi—1K3 1 kcal =4.184 kJ k3: 1.381 - IO‘BJ-K’l 1 erg =10’7J 1L'atm: 101.325 1 Noggin = 142.1 cm3 Firkin (US) = 0.833 Firkin (Brit) G =H — TS AG“; AH — TAS AG = AG" + RTln Q AG”: —RTln K AG“ = 2 nog— 2 AG? rxn products reactants Question Score 15 20 00 p—i U1 US 06 p—i O 0 oo ' N N O \1 1—1 9 O z 1 -ll 8 200 “U 9 :3 H m e-r E‘. m "U 93 Q ('9 E )8 N O ”v.-- NAME KE 8 Page 2 of 14 1. (8 pts) cocaine a. On the above structure of cocaine, mark all chiral centers with * . (there are "0» b. The largest ring has how many atoms? c. What type of amine is it? 3 0 d. Do you predict this is a strong or base? (circle answer) e. What type(s) of atom (what element) is/are at the bridgehead position(s)? C Points this page NAME K E i Page 3 of 14 2. (15 pts) On the axes below, sketch an energy diagram for an 5N2 reaction, labeling the axes, and any activation energies, transition states, and reactive intermediates. Wm i g "9 a; “1 3ft?" *" 1.4”?! «Q. [’0 a. Afiafi x 73‘ I \ .7» (5‘ 7"" 157:“ 3 V. } \ mo‘ E __ 1 - , . w \ . \ PWPY qfi X .1. V0! WQ’hG‘Y :‘flwfl reactants \\ \x g (g ( l4 0 For parts (b) through (d), write the product(s) of each of the 5N2 reactions, and label any stereocenters on the products with their R/S designations. H OWN To é 91w /\ <’ WOW 53?} (gr/xi? , (Z s’lrvclI/‘AI , :L («(mé‘flmvm‘lw‘) CH2CH3 y>’ir=fize;""§l?!-1’~"— CI 0 + 3 C 60 OH 3; d- Br + Hs—___,DMF Points this page NAME K E [ _ Page 4 of 14 3. (20 pts) Write the major product(s) of each of the following reactions in the large box, and indicate in the small box whether the product(s) is/are: A. a single achiral compound B. a single chiral compound C. a pair of enantiomers D. two or more diastereomers E. insufficient information to say what they are 3 cowln 3. ea Ci"\ or 114‘ b Bl'z _—__.—>. cc:4 Brz 0- CCI4 NAME KE I _ Page 5 of 14 4. (8 pts) For each statement, fill in the letter corresponding to the most appropriate matching item from the list below. Use only one letter for each answer. You may use a letter more than once. A. hetgrolytic F. endothermic B. hemolytic G. polar C. exergonic H. nonpolar D. endergonic I. vinylic E. exothermic J. allylic if: Gack A. Type of radical that is very difficult to form B. Reaction with a positive AH C. Regioselective bromination of alkanes Tl D. Benzene E. The way the 0-H bond in alcohols breaks in solvolysis F. Acetone G. 0—0 bond cleavage in hydrogen peroxide H. Characteristic of a spontaneous reaction EEHEEEIH Points this page NAME fig E _ Page 6 of 14 5' (15 pts) 2% a. The IUPAC name for compound-tar A 132"“ “mm 54¢??va 1w: (Hz, sm— aim «1.th 4-6%,. “fig. (“3’30 0" WA“? , «BC 1b The absolute configuration of the carbon marked >ki RJLW 5;“ 1 hi ,._ M Cl L . . A c. In the box, fill in the reagents of iiy/P‘E (6" conditions for converting compound A “WWW" {’ ”W 1‘3 to compound B. 2d In the box at right, draw the most (CH-930 stable conformation of B. Cl B (cu; 1—1 e. When B is treated with CH3O'Na+ in methanol, it undergoes {—2) Ar I) an E2 elimination reaction. Show the mechanism in the large ‘ _ box below, and redraw your product in the shadow box below right. 1. f. The reaction described in part (e) above gives a small amount of the 8N2 product. i. Draw the product in its most stable conformation in the box below left. ii. In the spaces below, indicate two modifications of this reaction that would enhance the yield of the E2 product. ICON Ed: Points this page NAM}; 146:6 _ Page 7 of 14 6. (28 pts) For each question, write the missing information in the boxes. The information may include reagent(s) and condition(s), or structure(s). If there is more than one product. indicate which is the major one. 2474443 (fr FOX 0H1 1 W W cis-1,2c:yclohexanediol (1113091 __.__.> CH30H2C ——'CH2 0 CHsCHzT CH3 9 CHgCHz. 0 __CH3 C' OCH3 The mechamsm for the second reaction 15 3M L (11:!) C_ /\/\ 1—181- ' 11320.an Ai w Hz/Pt —_> {12'} d./\)Br\- .‘BKOK‘4' /\/Kb ~1 ,1 117.1111: Immhrr (.4 \rs< 9 ”9444444 444444‘ :"174’, \\-‘U r153:- ‘ 4 4M“ 243744494: (4“ {“11 )4 446,4” '7 41am {7,1414144’ 4414414 4 44444 \4 + l/\//\‘) g 7 “1 3 4 Points this page Z NAME éE I Page 8 of 14 7. (10 pts) In the boxes, give the correct structure for the following compounds. 1,: a. (Z)—3—fluoro—3—hexene ‘/ b. sodium acetylide ‘2 c. 1—chlorobicyclo[2.2. 1] heptane ’x d. (2R,3S)—3—bromo—2—hexanol v‘ (draw as a Fischer projection) 1 1 i Points this page * O NAME___ éE i ____ Page 9 of 14 8. (10 pts) Consider the following carbocation ('9 a. What type of carbocation is it? CH2 2— #:86021qu (i 0 hatjl :; 31:3) 2_ b. Circle the correct order for carbocation stabilities: 1. l°<3°<this type i 2. 1° < this type < 3° 3. this type< 1°<3° 4. not enough information to say (/9 c. The carbocation is redrawn below. Use arrow notation to draw in the box the resonance structure(s) for this cation, including all major contributing structures. Points this page NAME KE i Page 10 of 14 9. (20 pts) For each pair of structures, indicate in the box at right whether they are: A. a meso compound B. a single compound that is n_ot a meso compound C. a pair of enantiomers D. diastereomers E. unrelated but real molecules F. impossible molecules Note that you may use a letter more than once, or not at all. 1 . H Cl 1. H7; 'H H3O —<CH3 Me H Me ii. H H OH COOH % H -—OH 111. i H —OH COOH HOH , \ HO HO iV. D HO fi/H H OH OH C H CI - 2 H3O ’ V1. NH5 + // \\ H: (QCHS HO OH Me H Me vii. E PR3 DMSO HO H H COOH HO H Cl viii. C Lb HO H CI COOH HOH HO , I HO H H 1X. C Br/k-UIH Me H H OH Me ET OH = CH3 Q x. mm W. Cl OH Points this page NAME iéE SA .— Page 11 of 14 10. (25 pts) For each question below, write the word tru_e or false in the box at right. .0. » .2 (up i 2‘ A. A stereoselective reaction may be enantioselective or diastereoselective. B. All stereocenters are chiral centers. C. In a stereospecific reaction, the stereochemistry of the product is independent of the stereochemistry of the starting material. D. Tautomers are special types of resonance structures. E. Steric strain is also called nonbonded interaction strain. F. Angle strain is one kind of torsional strain. G. Autooxidation is what happens to cars when they are left outside. H. Optical purity is numerically equal to enantiomeric excess. A little algebra interlude: a 'v 'I‘\ m; ( <2; "i J I. You run a reaction in which the product is a 90: 10 mixture of enantiomers. What is the ee? J. How many rings and/or double bonds are present in a molecule that has the molecular formula C6H902C1? K. The fluorination of alkanes is highly exothermic. Rounding to the nearest integer, predict the ratio of 2—fluorobutane to l—fluorobutane that would form upon mono-fluorination of butane. {gig-:1 Big BE NAME_ SE a Page 12 of 14 11- (11 pts) a. Compound X at left has what functional group? O ’7 A.‘ X \(E‘TO m? b. Compound X can be made by hydroboration/oxidation of an alkyne. Draw that alkyne in the big box at left, below. c. In the small box next to the arrow, fill in the / conditions for carrying out the reaction. M. .7 . Mm”- ,fls /.__——” M” /o‘r” 2 N92‘\l MD — L d 0“’\1\I“~€ dam/W" be??? d. Draw the product(s) of the ozonolysis of compound Y in the box below. L.” e. Name compound Y and specify its configuration using the El system. -M 3 «aw-Z—Wml—wagha Points this page NAME KE l _ Page 13 of 14 12. (6 pts) Polypropylene is made by radical polymerization of propene. Shown below are possible depictions of a portion of the polymer chain. The squiggles at the ends indicate the chain is much longer than what is shown. Structure A shows all of the methyl groups on the same side of the chain (“isotactic”). Structure B shows the methyl groups randomly on one side or the other (“atactic”). Based on your understanding of the polymerization mechanism, which structure, A or 13, more accurately represents the polymer that forms? In the box below: briefly explain your reasoning. Cbam (WOPQCWWVV‘; irwdwoi 04M WV? “fflfifir‘ r1”::3"-‘“' ‘s. U Lire, ( loam T0 43 (CA )3 Ef’m 3- 39 i/ “l 105 ’3‘?” i , j ‘ f 29% 3“ if) {\ka x} ‘3 a 1;“ “Hi” {W 1’“ j X}"’{ ,2???” {a . {£51.85 a?” (i g 4 I; $3,331,» 3:” 5»; ,: of , C '1 be «80 (“Wm ’33; (10* (3+6); (0 (tulffi tu‘f’ ,. \ Points this page NAME_ KE I Page 14 of 14 13 (24 pts) . 2.7 llt’ a. Circle the compou/djhatmlLshow a greater rate of SN 2 reaction with KN3 in acetone. C93 CC V b. Circle the compound that will undergo SNl solvolysis 1n aqueous ethanol more rapidly. m \ \ \ \ACI Cl/ \\, // \\___ MW“ 0. Circle the compound that will undergo more rapid solvolysis in aqueous acetic acid. / (CH3)3CBr \) it A ‘\ Br \ \ w..."— d. Circle the species that is likely to be the better phase transfer catalyst for a reaction to be carried out in dichloromethane. e. Put a circle around the species that is the strongest base, and a square around the weakest base. . , _ ”fin-j ! <\""Hc=_0'\ cr CH3OH “hwvhwafl .,,, ... v" f. Put a circle around the best leaving group in protic solvents, and a square around the worst. ‘\ OH' \_ RSOZO' or g. In each row, put a circle around the species that is the strongest nucleophile in water, and a square around the weakest. Mm F l Points this page C" if) ***TIVW SSV'IC) LSHIJ*** ‘01 69SI-S6006 VD ‘59193‘1V 801 699196 X08 'O‘d afimsod V’ID f1 Ansgwaqooyg 7g finsywaqg Jo mewuedeq 1191199 “ICIOH 101d ...
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