118BWin08FinKey

118BWin08FinKey - 1 Reactions(24 pts Draw the structure of...

Info iconThis preview shows pages 1–9. 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
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: 1. Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. Br A/ (CH3)3CO'K+ o \ Um: A) (CH3)3COH' L1 pls ' H 80 / 2 4 H B) W H20 fi/V \ ———» “V / ‘63 C) l / 7 § ~ 0 .. 29‘s entitl- Heb N02 “(02 N01 HN03 (we \ l D) ‘ ‘ \ H2804 ’ ’ ll‘9" madn- Zpl‘ oa E O 1) CH3CH2Li o” /ofi \ ’0’“ (Yb H + <1 2) H3o+ \ "2C 3 z W5 PB 0 1) NaOH 0‘ 0“ 0L" F \ ) H 2) CH3CHZCHZCHO H >\ 2913 (add slowly) ‘1 Ph 3) Heat 2. Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. G) Vv Br2 % \b—A CH30H I OCH-5 «4:313 1&3013 N NH areu‘l-fl [email protected] a, 7'3 g H) >__: L153 H ~/ NC ~ a h t at 0 +1 L wrow§UC&€[email protected] /5\ Hots NO wk 2 1)Zn(Hg), HCI, heat q q J) ’ \ i \ 29‘6er omw'thm 2) 012m: 3 C“ W5 O 2’ 3 0 rmull‘ I; K) \/U\/ I CH COOH 1PM" “a b I «1? o o 9143 L) fij 1) (CH3CH2)ZCuLi L “twink-:3 itflpk 2) Ll P33 3 3. (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. 0H 1 H 0A ,H O,HO+ M) Y\ ) C)2 ZS 4 3 Wk > 2)NaBH4 N) /\ 1) NaNH2 /\\ H t\ 2) [3. Chem?“ 3) Hso+ OCH OCH3 1) CH CH COCI AICI OCH) \ 5 3 2 , 30(3) A 0 © 0) ‘ \ 2) H30+ ‘ /Aé OCH; 3) Pd/C H2 m5 % *5 OH ‘ o @ 1) P00 P) /\[)\ O / I 2) CF3COsH Wl ‘Ipts 0 kc>c <1?“ 1) PPh3 Q) A/Br 2) CH3CHZCHZCH2L1 \/C 3) L' Pig 6’ o O \ H \ O / (.3l"|3(.-;H2()—l\la+ \ R) <5 Jr/fik/ °r \3 “I? %fl5 0 4 £3323: \ 4. Mechanisms: (30 pts). Show the detailed reaction mechanism for each of the following reactions. Include the structure of the expected products and all relevant resonance structures. CH3OH ® A) /U\ ' (D 14-60 H q!” G) H2304 C q [email protected]/H H50" o/H ‘@ .‘ H :2 )‘Lzzifiifig\ “We (Lu-50H {49%DCH3 OCH?» " 093 K’HSOQ' 653°“ w“ ‘ use? HGO’CH’ 4R 1 ® ® 0' A4 :3 ©0‘CHB OCH3 CHz’Oi/ OCH C2) »1\ / 3 cm3 0 90“ Q) +HzO ® of“® y’NHl NHz—NHZ mam 4i NHeNHz ‘ ® .. \h r, “O 2 9»: Egg“ New WNH (fig {4.75.9 H 5 - s (D H10 mg, 6) O“ 0* “2° W 0 9 "o 5 +0H 2’ 5. Synthesis: (20 pts). Show how you would carry out the following synthesis. Include the reagents you would need for each step and the intermediate products formed in each step. Br?H \ 0A —-—-——-—» fl OH ImCPBA- i3rz® Br /13H3°* @ Ere/Ye; r Br 2 TNBshy G M @Né) b3 Coo on. lzwaotz© Lag?“ WJ' TN‘INHag) 244 n-qutz // o 0/ “a r Lthqu + 14 Fer 0509 /H;o (0 Any Correctsynfiesis getsfil‘ Credit. 3 6. Vocabulary: (26 pts.) Fill in the blanks with the appropriate vocabulary word. If two words are given circle the correct one. A) mCPBA will react faster with a or / less substituted alkene. B) In the electrocyclic opening of cyclobutene with heat, the reaction proceeds in a Con Faker)! direction. C) In an anti-Markovnikov addition the nucleophile adds to the lCSE $03 side. D) Meta directors have a partial or full Eoéflive. charge next to the ring. tvfi «it Give two examples of meta directing functional groups N0! g E C30 SogH I (TF3 Q'lt . E) In general a ketone is more stable as a carbonyl geminal diol. F) In general a herniacetai can / cannot e 1so ated. An exception is C Cllc (I Olfhemiacetals. 7 G) The pka of the hydrogen alpha to an aldehyde is about 10 18 25 l 35 / 44. H) The pka ofan alkynyl hydrogen is about 10 / 18 ® 35 / 44. I) In anti addition both groups add to the same side of an alkene. J) An aldol reaction always / sometimes / never works with ketones. K) An activating group a electrons into a benzene by either regengn cg or induction L) A reaction under thermodynamic control tends to give the 55 graducl while a reaction under kinetic control uses the WM: . U a M) A P ml: (15)) gr # m i can be added then removed in a synthesis to prevent reaction at a particular functional group. N) Friedel-Crafts reactions work poorly in the presence of m gfi directin cups. 0) Altrisubstituted )trans / cis alkene is most stable, while a trisubstituted / trans ene is least stable. P) An aromatic ring must be fliangr’ , QICI g. g , gen SUQQJM and have HQ +2. electrons. \Pf- perqnsuwr 7. Coupling: (4 pts). In each indicate which proton is described A, B, C, D or none of the above. R'Hd A) A proton has a chemical shift of 6 2.69 ppm. It forms a doubled doubled doublet with the couplings J= 8 Hz (d), 2 Hz (d), and 1 Hz (d). Which is it? fl fl B) A proton has a chemical shift of 6 5.02 ppm. It forms a doubled doubled triplet with the couplings J= 8 Hz, (d), 3 Hz (d), and 1 Hz (t). Which is it? 'l‘l B 9. Nomenclature: (18 pts.). Give the proper (IUPAC) chemical name or draw the structure of each of the following compounds. Br Br £11965)- 2 , ‘i- AkhromovS-ehMmoleca-z,b-J:e..- A) \ \ § CIA/hf- - / m— mml PMle , 3-emnylp'hmfi B) 3—- (l-emnyn’ "herme 196mm, OH OH 0 C) G’hvclroxv 5mm hep+~3en-,2-ong c: D) / / (liHH'Qfi‘d{%M’3-ohloro—7—e1k1‘Hana-2,943, Br Br OH W 35"4- mth~1\oc.‘\’-3*M-7—~m-’l-¢\ E) i O 3- i septa pxfl - 2~mehv7i - 5 ~ph<n~1\ ' F) H {’2th .1 following proton and carbon NMR spectra. Significant IR peaks were also observed. Compound B forms afier reacting compound A with an excess of LiA1H4 followed by H3o+. What are compounds A and B? 3“ 2* 3H :11 m 2% 8 7 (yak as 5 HD 4 3 HC 2 1 2‘1; \ \ \ \ I 200 150 100 50 0 IR: v 3300 (sharp), 3100, 3058, 2950, 2200 1730, 1600, 1210, 830 6111'}. HA=1HJ=8Hz(d),6Hz(q)2Hz(t) HB=1HJ=8Hz(d),5Hz(t),1Hz(q) Hc=3HJ=6Hz(d),1Hz(d) HD=2HJ=5Hz(d),2Hz(d) Compowkk '2 Comma“ B /‘ A) /\/ O \ 10 ...
View Full Document

{[ snackBarMessage ]}

Page1 / 9

118BWin08FinKey - 1 Reactions(24 pts Draw the structure of...

This preview shows document pages 1 - 9. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online