Summer 2004 test 2

Summer 2004 test 2 - /. Chemistry 227, Summerl 2004, Dr....

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Unformatted text preview: /. Chemistry 227, Summerl 2004, Dr. Wells, Test 2 . ~ we!“ . ‘1 ; 0 were ‘10“ a (LAW Name. flag 5/317 {0 J him by? $91M 1. Chirallily. { i 5 points}. Give R and S designations far each stereucenter 1n the meieeuies below. .I fill ‘ H)“ a? L CHE-CHECH3 *~ C64) (93.” L “/ \"”””(:HECI+J3 H A CH3 2. Chirflllil}-'. 5 pninle}. What is the maximum number of sterenisemere far the compequ hfliflw. Show your wnrk and explain. 3. ohimtlisr. {i910 points}. o: s s o 3:31 Brim-@j'TMH CI compounds Complete The relationship table bflt‘fii: using 111:: following relationships: idontioaJ and moso identical but not moso ouantiomors diastoroomors oonsljlulionol isomers not isomers Nam: compounds 1, 2, 3 and 5. Us: R and S whore necossary. Compound I ) '- 2‘— bf'flmfl '3" 51"“ L“ “3' bu» 1%“:- Compound 2 Compound 3 2.3 323 ~ ‘* 1R M23” H hair Who 4 rotsti onship —! Compound5 LE} 2 r— flfem+ {xx/MU 4. Ionie reactions. E 5 points). 5. 6. Pr How does solvent eheice impact the rate of an Sal reaction? Consider polar aprotic solvents and polar protic solvents. PAH» Saws—ll?) 5le-J SNZ- Matthew lat? mi“; 5r”- W amtwrms ionic reactions. (a) Li 5 peints}.Consider the 2° alkyl halide substrate reacting with F'. In light of que‘stien 4 what type of solvent would most liker cause the reaction to follow an Sal mechanism. Explain. Fla m sauna l: (ls—7L P.“ JG“) we; w M .. slew-l lit “Wlwl‘m‘ll’i’ evil/th “n‘l Wig 5:41 matr— M‘s"?- tB .- .-- .r .- Pr\t C——[ / H let] = + 1?.9" Ll {h} t S 5 points}. If the reaction did llJllCIW an SN] mechanism «only what single measurement would indicate this.- Explain. 5“ l. erh-llé. j) lull-:1 {film It: h Il'jL Cot} 2: 0”. [1r __ 2 points}.SNl reactions ot'a chiral substrate gives a raceniie mixture product because the carbonation intermediate is planar tr" E. the'carheeation intermediate is tetrahedral J": C. the nucleophile attacks the @uhstrate from the back or the front. )1 D. polar solvents are required :1 E. high temperature fill“) is required ,R 7. Ionic reactions. [E10 points). The reaction bciow gives a mixture of products. Write the Sol mechanism and the E2 mechanism for the reaction. Used curved arrows to indicate electron pair ntovcman Show the correct stereoohcmistry ofthc product and transition state for the SHE meChanism'. CH3 \ ,cttg, .——.— 5N2 product + E2 product Cansider the reactian beIew for questians 8 and 9 /\/l\ I DMSU /\/l\ - + K -—'I- i Y 3. s1»: x The. 8. [22 points}% rate bf the reactian below is greatest il" . a a 51L UM, il- ® " i i m. a. Jah- " X=F,Y=I i: be: int-«emit ' ‘ PS B.X=I.Y=F “tripfii them 1min C. The nature (if X anti Y do not affect the rate matter in an 8N2 reaction 9. I: Di 4 pbintsp‘k kinetie stud}.a bf this reaction was performed with X = I and Y = 1h. The missing number in the chart below sbbulii be initial [substrate] initial [in initial rate imnii. '1 5"} — aaeia imam 4.00 x is '- aflflaas C.£}.D{}2fi Dentist: P“)?! : RLSLHLKBC rte-.3 _ _ _ . _ _ . . _ _ . _ _ _ _ _ . _ _ _ . _ _ . _ . . _ . . . . _ . . _ . . . . . . . _ . . . . _ . . . . . . {2-2 paints} liming: wants to make 2-brbmb-2-ineth3i'lpmpane 1" mm 3-itidfl-lfl’lflfl'iflpl‘flpflflfl . Earl affers some adviee. “Jimmy yiiu might tii USE Stilt-eat He; base and run the reactii‘m at , and bi" course use Br" as a nuelebphile. 1 mean it new; db _vbti hear me ‘3‘“ (_I e‘" D a. efl1aaal,DH'.25°C U a. DMF. Dl-I‘. 25“e__ ll {1H3 _ _ ___ _ 11"”..- C‘. ethanal. na base.25”C \i HHC 1 D. emaan at: base 5U” " (“a E. EMF. (CH3}3CU '. 25‘s.: DMF [_dimetbyfiirmamide} Ciinsider the plat an the right far questians 11 and 11 # l3 1 1. The agfitibn energy for the 8N2 reaction is keali’mbl. {write the number] i3 . _ e: l I i [AZPDinLfi] :3 :lefi-wa 9 all 12. The trasitibn state is labeled by . A. it C. 2. D. it is not abelecl in this plat E. there is no transitien state to label! {_ Elpaints} I LII |. J '1...) E Te" u _s: :- Dr I— U I: U reaetiun etibrdinale ...
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Summer 2004 test 2 - /. Chemistry 227, Summerl 2004, Dr....

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