practice_final_key_from01

practice_final_key_from01 - CHM 2210/0767 NAME (Last,...

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Unformatted text preview: CHM 2210/0767 NAME (Last, First) Final Exam SS# MayZ, 2001 . a L~ 1. opts.) l pawl ear—L |—ar Elva + L» IR 3) Circle the most stable carbocation. GD b) Circle the most stable alkene. W vs_ 0) Circle the compound which contains the most acidic proton. M vs. d) Circle the compound that will react faster by an SNI mechanism. 0 n as. e) Circle the compound that will react faster in an SNZ reaction. .Jv r). Paid; c ch (4 pts.) Name the following compounds. OH #1 WW“) r3)” lSOEWEIlELmd' SJ, 54,-;uud“ Mme 3—(I—mll,aa+t7i) (Flat) H1 5‘; M (\maJ “‘5 "‘ 9Ltn0‘ b1! "I no :2- _ .—-\ Pcr OVhL‘r/"D M—‘Oi‘z‘c ‘ 2,.» -~t MM) new M on W V l ' 3 ‘ q, '3) —— _ 32 "QT-“lb "(3" re l“ 7~Unclaqaal¢4e 432,1) 3. (6 pts.) Draw the three most stable resonance structures for the radical given below. Q. Pubs-3'5 final-s S-J—ruclurc (all 0" ndL’is F6! full? box) 4. (3 pts.) Consider the following pairs of structures. Identify the relationship between them by describing them as enantiomers (E), diastereomers (D), constitutional isomers (CI), or the same compound (S). CH20H CHon l par}; | H H Cl t ‘3‘ ‘ L 3. VS. = S c: H _ H l “"— CHZOH CHZOH (In T“: “cc C-.:m”B E b. H\\\\ l r .3! \CH3 VS Cl/ \H d\ '3‘ CH3 CH3 \ Q o: H H or D C. H Cl H CI 5.0 pts.) Convert the dash and wedge structure beiow into a Fischer projection and label each chiral carbon as (R) or (S). L‘ P911545 rid-«l 6% [Br "—“—-'—"'—'_'_——" '1 __ Ll Jed-J1 HOHZC\C/Ca\C/C¢HO | up 5: r. \\“"- x". . F\ \ H\\\ \CuH=CH2 H. ‘ Per sec L 9t j (I Cam: 5'“ now-ltd '2 or S “'4. F9!" 8 (-9 ll . ' I Identify the hybridization of each labeled carbon in the above structure. to C 4'” CJ' 3 5&0: arcus W c 2 “i “it '1- La w I c. Ch 5 _SP__ O 5 0‘ 0 ‘1 Cc =_S_P_ 6. (7 pts.) Draw Newman Projections for the two chair conformations of cis-1,3- dimethylcyclohexanc using the C1-C6 bond and the C3-C4 bond. Circle the most stable conformation. Cu“; CH3 ow W29 51 ’3 Pair}; p‘er (9ch fit: Sire/aim: l paint Far crrolmj +La owned— one. 7. W? 19*) b. Ar Na] Br 5 psi/:45 :2ch Mac emf/‘1 (10 pts.) Write a proper mechanism for each of the following reactions, indicating the major product or products for each. For Co m M lac {MEL Nady-Ls (‘3 er"! 9 I” H (earsst Salty); gn— fit)” 0H + H 0 . . Q a. 3 4,!- wr‘m «may; A 9 ._-y (Jul 5 U! \ Bee 8. (40 pts.) Predict the major product(s) of each of the following reactions. Show stereochemistry where appropriate and include all stereoisomers where necessary. If there is no reaction, write NR. AA 0: *5 / a. I e°~° ((313)3(363149 A— u H 230% r O\\\ D 2PM“? (\u \9'9 M2» 5" °' ><\[/ Brz _ W “U PW"! hv "5 I ‘ HBr g “7—!” "I r} ‘3' M ROOR 8 r n P ' 0‘53 afar: J (1 o ' aQKSe- <>_CH3 1) Hg(OAc)z, EtOI-I 0(6) Ea IfJ 2) NaBH4, onO \ 4‘ >6.) 1) THF:BH3 5;” H / EL ’1’? E 2) H202,GOH ‘ on, 4- , a; o“ Wflkfig- M mm A6? 0:» par-mp A )6 % H so 'l a" PW”! (L? h. —-—g—4——> N H2304 ' ‘ ' runs 'VQwi. A\ mid/3:804 “‘1 ’F a} \ . \V\ N/ M CH3CN _ Cars) 0 Ag). (1/? j- /\)J\ l) 2 CH3MgBr/ether 09 c: 2) HBOJ, /\)< \ JET“ {\0 Q (L‘QKS O vchJC} .1 k A NaBI-L, {aim o N R o 5 GA A 1 LAH N by \Por‘r Eb O o no {A q/Q m) HUM l) 1 eq. CH3Man’ether A» Qef 2) H30+ H7(3\\ ,, A 955 5 «2' q"? n) | (er3 t $33"; of"! OH H2304 N Q C \M . a" Vt. 95¢ a, 1 x5 x O S p» " “a; ox Q )1)” H Lo 0) C1—-S—<:—->—CH3 a /Y Q) N \Dfi OH - u 0" J9; S4U€orj~1m [Vb-J]- L,‘ can {2” c :4- Earl. .4? Q, For Bfrmhofl‘fi Prue/{9°}- Of" ‘9 (Magi chi-mi}: QFOIV‘J’fle-Jlfi wit—Jun;- “‘6’. CWTde Cm”) m7 “PL {POL in scch bane HQ l Chum-‘10! 1‘11 C'NQJ'L) 9. (18 pts.) Complete the following synthetic “roadmap” by supplying the structures of the major products of each reaction in the boxes provided. Fill in any indicated reagents. If you need, use the extra space outside the boxes to work out the reactions. ’59 H26=CH2 _Ph‘223_H_._ /0: l \. smas- sot!” “1+ H3 0* ' 5 7m" 0 M C10 M 0H H2804 OH _ N-H Cl'OgCl‘ Q,» \ / '5 CH2C12 O“ 1) NaCECCH; a M 2) H30+ Mk zvb as H “‘ \ + 1)Na 2) CH3CH21 w\ EXTRA CREDIT (10 pts.) Propose a mechanism, showing the initiation, 1,4-propagation, and tennination steps, far ,‘A the free radical polymerization of butadiene. Use a peroxide (RO—OR) as an initiator. J H‘ POT {field (firms/6+5.) OJLIW}SL core-at?- ‘oT Sccfic’n 3PM [‘nflrcrifi. ...
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practice_final_key_from01 - CHM 2210/0767 NAME (Last,...

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