CHEM 313 Fall 2014 Final Exam Daytime Name \< Ee Y 1. For each series of three compounds in the second column, circle the one that is most reactive in the reaction noted in the far left column, (18 points) Reaction of Interest Choices (circle the most reactive one)_ Pis Benzene HNO3/H2S0, _Nitrobenzene |e Me COOH Derivative Derivative ex Vs Ce « » CL (1e. Electrophilie Aromatic Substitution) ‘OMe F ‘OMe ‘Same reaction as above LO cl HOOC" ax —NSOWe aroMe meh, > cl NC. ‘Ar= aromatic compound CK « “oO,” »( (ie. Nucleophilic Aromatic Substitution) No. NO2 RX + NaCN ——» RGN + Nex 5 B ve OTs (ie. the Sy2 reaction) OTs vs NBS FySO, Alcohol — =» Alkene Heat ‘Same reaction as above ers OF a . akon vs A~vom \ Pay \ (i.e. Acid-cat. Aleohol Dehydration) 2 Asin RIS to each chiral center and F/Z to each alkene group. (8 points) Hi oO vt ' je ame" = ey F ‘CH2CH; ~ 2H CHCHs: ‘ CH S R 2 E 3. For each name below give a structure corresponding to the name. For each structure drawn below give a proper IUPAC name. Answer in the same box as the name/structure, (8 points) "nitrotoluene cH ‘4-chloro-I-pentyne oy lor Z ON- aN Tone ins 1=chlory =3- mre Pyle ot ; i (don't forget cistransy Cy Clohex ane OT Scchlory “5 ~ me Hyle 2-hexand (344, Perform the following tasks/ and or provide the requested information for the compound depicted in the box, which has a net +1 charge. (8 points) a. Place formal charges at every atom that has one, b.There are__3 (how many?) r-bonds in this molecule d. The N. Ip/sp/| 5. Write two resonance structures for the following compound. (4 points) Bu Br H & 4 * CH, Me ex” er’ -—- &@ — CL 4 n 6. Over the word Vs, write “e” if the two compounds are enantiomers, “d” if they are diastereomers, and “I” if they are identical compounds. The last one is a Fischer projection. (8 points) O € O “cy o Cl., Oo cl, GOOH | cl, S0OH A te cel Ho. Vs. Me, OH 0. OH He OH CHCl 7. Draw a circle around ANY ONE of the meso compounds in the previous question. (2 points) 8. Supply each requested piece of information for the following of — acid/base reaction depicted inthe | box. (6 points) a. This reaction will go to thee) right; circle one). », The approximate pKa of the alkyne is (5 / 10/20 () 30/35; circle one). wo) + 0) ¢. Circle the species in the box that is the strongest base. 9. Circle the three compounds below that contain an aromatic ring system. (6 points)10. For each series of 3 compounds circle the one that is most stable (lowest in energy). (30 points) Series of three Sal re ‘Answer to QII (only 2 required) 3 men the other 2 choey D-crch,ch; Vs One Vs Oeenacs have Severe Owusle sto en “i We Lie Vs fee) vs AIAN the other 2 Choices have Stenc Sheu bebvela, Hee ne toe | genes Me GH cnn 3° >2° 7% fer Free racical stability the @clpeck ore bas Jue the otter shegseraph one has weve Gitucke Tats, torial ptryn the other cholces have sp? C's ae rikgs thet Me haga ae Shady The evcled on ay Boe doubiy allylic, Other arc FT stnaly allylic + just 2f the ciclecl one 1s con), and fas & higher Clee ie of alkyl subs ead. ab ts, “oon _PhCOOOH O WR Has © P "CHOW ZX CS cd 4 (show stereochemistry) s _ > Me fi 4 Me—= a uindlar ¢ Nh ph H, { V a tlys T Z Heat ‘Me "=. 2 * ff Me > co S cI = 7 1? 1. $03 7 H,S0q 2. AG IRG Bey14, Write ONE AND ONLY ONE letter for a reaction in Q12 or 13 fitting each description. (10 points) a Areaction that proceeds through a carbocation intermediate. A BCEGH?7 NU b. A reaction that proceeds through a fre radical intermediate, | NV 2 «.Areaction that occurs due to favorable HOMO-LUMO interactions involving x-leetons, © T_ QZ 4. A reaction where the product is optically active. TK e. A reaction sequence where at least one step is an $y reaction. JKL H f 15, Perform ONE OUT OF THREE of the more advanced problems on this page and the next page. If you do ‘two of even all three of them only your best one counts. Each is worth 10 points. Option A: Multistep synthesis. Outline all steps that are necessary to transform benzene into compound A. Be especially careful that your substituents end up in the right places (e.g. o,m,p) and that rearrangements are not occurring. Use any alkyl halide or acid chloride as your source for “igre carbon atoms. oi BA ye ald; Br Oo steps 3 Pulte or MANA, [Kcou// reett CCl [Ree 0 Br, [ Fe Brp «lau cant be Used se ADBC best since pp 7° 8-@® aa By a i" ct ct \ l - ©, @ S-6 SG oN (SoOption B: Mechanism: Write a mechanism for the following reaction. Cl AICI, (catalyst) ° CoH C10 CioHyo O | \ Minus H* eo -Atels ; + Z Co) Has aca? | Se Ca SI : > — e , u ive . 5 0 A = ex's CroH AICO CroH10* (one ring) CoH 0° (two rings) Option C: Mechanism: Write a mechanism for the following reaction, It is OK to show the mechanism with HT instead of HS as you illustrate the mechanism, Hint —the reaction starts atthe alkene, not the aromatic ring.