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Chem 2211 Exam 2

Chem 2211 Exam 2 - NAME GHEMI'STRY 221-1 Em 2 3 July a 2mm...

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Unformatted text preview: NAME GHEMI'STRY 221-1 Em 2. 3 July a, 2mm - Be awe to read eaeh queatiea carefully. This teat must be eating in gen Teata. takea‘ m m pencil will not be graded Partial credit Will be. assigned where appxepriate Te rewitte full eaedit yea muet attawer the= queafien (temp-lately. Relax and gaad luck“ I E 1. (191 pa) Provide the prdper FUPAC names for the fallaw'mg'eempuunda imam 1 apaeea'prnfifled helm: 3+ 4. E" :5. Tutal: _ e-JLI—mglaaal) ma. hit”, W, or (31, 5‘53- art-Earl- b- Milan-I9?! —L—- mats?!— gfq.‘ pnhiFe-‘tg. 1 the following: M Draw on three staggered conformations, circle the least stable conformer and calculate its total strain energy: 2. {It} points} Looking down the Carbon 2 — Carbon 3 bond of 3-methylpentane, provide | | | l . least- Total strain energy for he mount-stable eorifonner. Draw all three eelinsed conformations, circie the most stable conformer and calculate its total strain energy: (NH on No.0 . Ina 4L one o a”: Host- Tetal strain energyr fer the tenet-”emcee conformer: 1 | :35 K‘s/m 1I 3. (It! pits} Draw a reaetien'en'ergy flagrant that eerrespendste the-fMlhwing criteria: i. The first step' ts the fastest fifthe- the-fee amt! has a pesifive 5H“ ii. The seeend step 15 slow and exethern'lie iii. The third mp} is fast and has a negative at}? if. The reeetten’s overall K3,} 1 Clear! “label each individual ste 's-aeflvaflen en ' and trensi 'en state-as We“ as the at?“ ef the ever-all reaeflen. Make Sure that year'laheltng is neat and clear: 4. [6 pts) Drew structures for the major productts) of the following reactions. [Hint- think regiochemistry]: Bf V Ether. 25°C HG Ether. 25°C Br- HBr ——h‘- Ether. zstc W Jr 5. {4 pts} Draw the structure-(s) of the appropriate-starting materiafls} that will produce 01313 the indicated product under the provided reaction conditions: 6. {it} pte) Add curved arrows to the mechanism profided below to indicate the appropriate electron movement'in each step: fl 03% 033? 0H H .r’ E) ”e. fifl w + H25; 1'. {6 pts} Assign the appropriate EIZ stereoehemlstry to' thealkeaes provided below: H??? _C>:(c: a a E H H2GN JHseo EN / ll. {4 pts} Calculate the degrees of maturation in the following molecular formulas: CmHflBTNzfl Curflzaflcfls ‘53 _3_ (anl‘flz, = H2, H1: l' l l" {'23 = GIL;- He-Lee to: = E (Hz) (1711M? 31...- Hm 1*? = 3:: lip-30"»: BRL‘S 9. [ll] puts} Idenfify the following reaetiens as additien, elimination, substitution? or rearrangement in the hex provided to right of each .eqnatinn: Er '.e: own—*0 :5 DH .d_— U WC“) SLAB Bh'hfi Han 16. (It! pix) Indicate whether the fallowing pairs of compuuuds are mnsfimfiunfil isomers, stereuisnmers, mnfnrmatinual isamers', or identical in one anomer: 1 aims}: TCLEA +‘ L “A EH3 1:95 I .3. ’5- CH EH3}: L '5 é ; :H3 3 I CH- H Ha'; H H I C] CH;- _ NH2 . fl 3 T. H £4: ‘7: H 3 CHO _ 11'. ('3' lite) Draw the two possible chair conformations of the following compound. Your ‘ structures must adhere to e indicated numberin Scheme. Calculate the total strain energyI of each conformation and circle the most stable conformer. TotalStrein Energy: I O [L‘s/rm” TotelSirain Energy: '7 :2 Kjfiuull ali'rO‘Ze integrate £12.91} 3% |xi~'-1=1.l1 {3 pie} Draw the moststahle conformation of trolled¢thyL3—ie'opropylcycloheme in the box provided below: 5:4ng H he’d—u- wan); —__——,_.___.—-—-I—-—-I—-'—'—— 12. [11] pt} Calculate the heat of farmafian (511°) for the fallawing reaefian using the appropriate hand disaaeiafiaa energies found in the tahiesprefided with your test. In arder to receive full credit, yau must show all ef year work: '13”: _ .Ti'la /fi"‘a~. 1- Egg ——IEEt_p.. .?\ + HEr Ha ' at 533KB.- CH: Radiee! Erminatian of leahu ta'rre (599% “1'1 5‘10 meal (CHaB3fl-Er" 2e} Kym Eaf- Ear HB Rifle-.1 H—fir Blah: lawn...“ SEE-3 klflmt (0:23} 1&1qu M“ = 383"W = 41L; Kym / Calculate the at}? far this rea'etian iffl1e change in entrapy is‘ as" = 0.1125 1(3th at'a temperature of 311132. Shaw yam“ wark: a It At: s AH °- .- ‘r as A195 = C” Ht, m/ml) - (‘srela x 0.0;? KI/(Kflflb £3. ...
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