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test3key09 - Chem 345 Final Examination Name Wednesday...

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Unformatted text preview: Chem. 345 Final Examination Name Wednesday, December 16th, 2009 WSU ID # 1) Consider the reaction AH + H20 S A” + H30”) For the following named acids: 1) draw the structure of the acid, 2) give the approximate pKa of the acid in units of 5, and 3) draw the structure of the conjugate base (24 points). ' Diisopropyl ammonium Hydrocyanic acid 3—Chlorobenzoic acid Propyne cation pKa It: pKa é pKa 25 pKa (p ' u i “ /\ 33A . a? C. ‘ nu , ‘ Hen-en L?" Hrc'EC-‘CHJ 6 g i C. E C. " CM, :2 1:: .. En \ ° J O Benzyl oxonium cation m-Bromophenol Pyridinium cation 3-Pentanone “I ' pKa Lb pKa [Q pKa j pKa 2 to 0 HI (concentrated) O l)? dried has hi ?'°P°“3‘~k em CVCH;£ me.—1—ga’t M“? (£‘1W-V'5549M Gas- albyma— )(u o. (-6 va3k-‘m Edi" 219+ 3) Ibogaine is a naturally occurring psychoactive alkaloid isolated from plants. Ibogaine is a psychoactive compound that has been used to treat addiction. Answer the following questions (10 points). H7300 a. How many chiral carbons are in ibogaine? g t . 13. Use the numbers shown in the structures to indicate all of the chiral carbon atoms. 11 I z 53 \q c. What is the absolute configuration (R, S) for C12. 22 L' (1. Circle the most basic nitrogen e. What is the approximate pKa of the monohydrochloride salt of ibogaine? [Q -. GMM $04 + 4) You attempted to synthesize 5-bromo—pentane—l,4—diol from 4—pentene-l -ol using bromine in water. Instead, you isolated a product with the molecular formula C5H9Br0. Draw this product and draw a reasonable mechanism that accounts for its formation (10 points) QJ+L9MPL€¢ [email protected]/fl3 behw 0,4 Q) \ ’vil \ Br (\A was: - l we. [3‘ cu Hat.) 5“ “Er m4 '\ .‘o'. 4 —P¢nl.¢m_| .. cl bWMflJM I ‘14 iM} I‘m/r C‘qu’BrO Tab/mmoleaqbr 43+“: Quanta Sin“, Limo-r}, uh's’rraMVci find" W—nu—u...‘ :0 .‘CM'P Q P CaibUCa‘l‘fMfi 5) Complete the following by drawing the missing starting materials reagent and/or products sand labeling reaction type ewhere required. Stereochemistry and regiochemistry may be important (38 points). ‘ a)/\/k ———:- M A 9) Br NaOEb’EtOH )\ ether X/ \/ type WW type L I gr 0 or! a NaBH {CH CH b) 0 M4,. I\/ W‘ O H h) m ) - 4 3 @K b) H 0+ 4’ Br 3 6/ type M type #Mrw— bi a) NaOEt/EtOH c? S: N 1130+ )1 . “Hz. —_—" ‘ Ph \ + C) OEt b) Neutralize . 1 late ') \é Ph 1% M 63’ type type imine hydrolysis )bfl /€+ou a ' bW 3" _ Pcc c (*ONKQQ C)N&M/H3°Q\A ’ CHZCIQ \/ . type m type * OCH O\il/ NaOH/HZO 0‘1( k) OZNQ/OCHS HN03 Z t 5 a I u Hgso4 a: h L WWW type 4 HM MgBr, ether in 03 0 0H 3)} H H V\n H ‘- I a mufilb OH type mixed aldol condensation type sad: 5 ”flank gt 2-: “1‘91“; 6) The following enone,,3—rnethylcyclopent—2—en0ne, was prepared through an intramolecular aldol condensation followed by a dehydration. Draw the starting diketone and the intermediate cyclic B—hydroxy ketone (8 points). 3—methylcyclopent-2—enone starting acyclic diketone cyclic B—hydroxyketone ...
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test3key09 - Chem 345 Final Examination Name Wednesday...

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