{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

CHEM_140A_WINTER_2002_NEFZI_MIDTERM KEY

CHEM_140A_WINTER_2002_NEFZI_MIDTERM KEY - aim HOP Wide/0061...

Info iconThis preview shows pages 1–12. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 8
Background image of page 9

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 10
Background image of page 11

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 12
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: / aim HOP: Wide/0061 DMA‘WM It My StudentName: q?" l‘ble’g’hr Nd MEX—Ll 1) What is the expected major product A for the following reaction. Show the mechanism. Problem 1 \fl—fi—I-Héd A \: C16 ( genial“ _C+> 2) The treatment of A in a solution (H20, CH30H) yields compound B. Show the mechanism of the reaction and explain the stereochemistry of the transformation. 0L4 “\ 5% ”‘ me C /J‘ o- “L A O < .. \ 1/”— \ a '_"2’ / / (R) H o \ z . l E) l\:l Q "—601 \/\ 0M __ 6 L/ / \ / Q , l K h 1 (j :_ \ z , H ,__;. {law/ ____; (s) a: 0 ” l W C l \ \ H / a Er) OJ Oil'- vfl‘) Li.» Km ~ H ,. i) "‘ tau 3) What is the optical activity of the final product? l—Cth'mniC, min-ure, -' Of>lxtal ac’lwilj 2 Printed with FinePrint 2000 - purchase at http://www.fineprint.com—» ~ 777477 / aim HOP: Wide/0061 DMA‘WM It My StudentName: q?" l‘ble’g’hr Nd MEX—Ll 1) What is the expected major product A for the following reaction. Show the mechanism. Problem 1 \fl—fi—I-Héd A \: C16 ( genial“ _C+> 2) The treatment of A in a solution (H20, CH30H) yields compound B. Show the mechanism of the reaction and explain the stereochemistry of the transformation. 0L4 “\ 5% ”‘ me C /J‘ o- “L A O < .. \ 1/”— \ a '_"2’ / / (R) H o \ z . l E) l\:l Q "—601 \/\ 0M __ 6 L/ / \ / Q , l K h 1 (j :_ \ z , H ,__;. {law/ ____; (s) a: 0 ” l W C l \ \ H / a Er) OJ Oil'- vfl‘) Li.» Km ~ H ,. i) "‘ tau 3) What is the optical activity of the final product? l—Cth'mniC, min-ure, -' Of>lxtal ac’lwilj 2 Printed with FinePrint 2000 - purchase at http://www.fineprint.com—» ~ 777477 Student Name: Problem 2 Name each ofthe following compounds, including an assignment of the configuration. ,OH 1 <i9> -— \— Fran \Looi'an— [L- o' 6!) H3C\ /Br I b) CH—C""u/IH ' (27$) - '5" ‘bVW-‘J — gone/+631» Pedant“ (5) H30 \CH20H3 (S) . (g) ‘ C) PEG/ma ({6} 26/25) ‘-’ \,2' &—L‘L.>Fsvm_o -q- mai'gjkflcjeOLQKa ‘ 2 (S) H Br - 333(1er EUi—CLF '1’ G. V m -1 \\\\\ 3, § I A «K9 4» 0.: 7n v l {\o 0’ HaC CH3 u H g (S) _ .1 _ or _ _ l—afl e 6) Br+CH3 : 6Q: ‘7‘; Q: (2 5) 2 .. grow a LN arbor:3 03%“; (Fisher projection) ‘ 04> CH3 ' E E.) (11 Err-’éfl H 2 .5 l’afl! 0| H (,8 ”*3 (“L03 r2fib— Aickeoro ~3~me ‘ f) 2';- \ KP}; Cl CHQCHa Ou K 2 g) 3 R.) 5 CH3 ‘ (Fisher projection) Printed With FinePrint 2000 - purchase at http://wwwfineprint-comi_fiwai , 77 Mi 77 7 Student Name: Problem 3 g / Draw possible conformations of the following compound as perspectives formulas and Newman 1 projections. Draw an energy diagram showing the relative energies of the different conformers. R g ‘5 H Br ‘J 9:" J Br / ’4, SK It I { LJ >- I... ’1' \ ‘\x {5/ \ H ‘ " \H . '1, L”— : / ‘ ' WWI/[H j> %)\\ / k H‘ “U a // I Lu H30 CH3 Du ‘ r: 31x b H V‘n Lu J /T ‘ g l, Er d) b er k; H U!) ‘ Br J , _ ,_.,.-.___.__._V_.,...., .4- H mg 1 an (Ms / Gr 0’2: / 8-7 /8 _,_.,,_ l [.1 Fl 2 I H k gr , r>__._\ I " A H’// > 3’0. / “>2, J : x90; {x‘ H 5 .4 OJ) Br j Br LA C Printed with FinePrint 2000 - purchase at http://wwwfineprint,comw7m .mm , , ,, ,,._ Student Name: Problem 4 Draw and name, including the configuration, all the stereoisomers that are possible for each of the i following compounds. Identify the enantiomers, diastereomers and meso forms. 8) CH3CH26HCHZC‘IHCH3 (LH3 Br enamfiémers m {2 l (a) ‘12“, / /(\)// ( > v \ "'7/ \ b i 61’ ‘\ ‘l‘pf elmswmw (4w r61“ 3 Atoslermte r 3 ,/, \4 K i 3- [W ‘ xii; \2/ Z ill 1 -L 3 v V J -nq Wm P” 3 b) A? A "u: 4 H H i H3C-—-C———C——-CH3 ; Cl Cl (Jug, (“a g DJ; (M2 t ‘ /’1 JVCtSFE'W—cw 979- A {QSLQF etc“ 4 F 5‘ _,/ K\‘ («~9- /, 0J3 ‘V Lt H fl\H C0. LU Printed with FinePrint 2000 - purchase at http://www.fineprint.comWWWWW WWWWWW W W W WW Student Name: Problem 5 a) Predict the following reaction pathway (SN'l or 8N2). Indicate the configurations for the substrate and the product. Cl M A t ie-H‘ Aflé + NaCN ——c-e—?2:——_> (8% CN LIA" \EMJNQ . ' I? b) Explain your chorce. 6 N Z , Qec‘i‘m Ami—me ': ail-0*”: "sd‘lfa'r‘ groom} (5000 *or Sm) ONO “”6. 4,, Nut. emf!» i1. S€Cmciari fitmvn‘ar P“ “Si \NQKMAI.) I" 'E reaction (1 c) Draw an energy diagram Student Name: Problem 6 How could each of the following transfor mations be carried out? Explain your reasoning by supplyin the reagents for all transformations. i H3C 7 a) >2 ‘ H _ CH2 M H3c-——c—-CH3 Br H H2N+ ! 0— Br \CHa \‘x e " Bra fl/‘J \ :3 04 OJ 5 / , ;;-—~ .3 ; > gf/CU5 H H Er "a. “a ' h) /\f/ , ’13—» /\'/ 0H «5 "h e... CN Na C NL// 1 //// (gut). /W/ // 0 T3 7 1 C) AK fl/ OH 0 / AQA,’ #0., 8 +‘/LHL Printed with FinePrint 2000 - purchase at http://www.fineprint.comfy MR ‘ Problem 7 Explain how and why solvolysis of 2-bromo—3-meth l ' ' )1- butane] as the major pmduct? y butane m aqueous methanol yxelds 2-methyl-2- Br r41 Printed with FinePrint 2000 - purchase at http://www.fineprint.comv7 Student Name: Problem 8 What is the expected major product for each of the following transformations? Indicate stereochemistry when appropriate and assrgn (R) and (S) to each stereogenic center. If no reaction occurs, write NR. a) (5) \' ‘ '~ g.” NaCN DMF 5'“ LMoMs ’ (a) ‘ H L A : <W of WWW) Br \ “kdi WM 2 (5) z 1)TsCl,pyridine W i C) ——————-—-—-———-> ’ 2) LiSCH3, DMSO A3 TSLQ ,fa/Haiflér Q (TOB\AL-fi~ ) (“ohm“) .L) Li 501:) {’3 0-1:) W Ts/OQHM /~‘ We) Printed with FinePrint 2000 - purchase at http://www.fineprint.comir~e 7m, W —- H20 Student Name: ._________, ”COQQ’gH + (35%éé i 03 (2) (“J 9“ (E) 3 W Foam}: mod-w (183 43619 /\ +1.9 q /\ ‘\ Z!” 6:6 _.V\ /\ Cu w u/ 0,, % + CH _—\4 Ga 2 Q53”; ‘ I». 4. "fig-fir . CH3 _. b e) l ‘ £32, at: h? Hac—C———C——CH2 4,. ' ——‘———"> H La ._ C H (at 0’3 Printed with FinePrint 2000 - purchase at http://www.fineprint.com— , ,, wrong finaid 11 Problem 9 S‘Udent Name: \ 12 Printed with FinePrint 2000 - purchase at http://www.fineprint.com " * "’ Student Name: 5; 0 _ ? {Tinséegelfollowing compounds. How many stereocenters are to each compound. 0 n.“ | 3 ’ Conro _u_ FfOFj\C3C\oPe "a ‘ 3) '5 ska-e OCen‘Lfi“ S b) Q,mc}e:>l -l-Jlg- CLPLenf -k‘xqfl‘c‘p — Z -— 0{ 3 §€r€OC€nL€F€D HO * 4‘ Q0 c) + 51- Q ~Con€OePefl\ >33? ‘ kexcm .. ‘ 4* *- Cl 5‘ fi‘rermtenltet‘fi. Printed With Fineprint 2000 - purchase at httpy/wwwfineprintcom 7 , if? 7 7 7 ...
View Full Document

{[ snackBarMessage ]}