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322bs06_e2_key - Organic Chemistry 322 bL Spring Semester...

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Unformatted text preview: Organic Chemistry 322 bL Spring Semester 2006 Exam 2 Wednesday, March 1, 2006 Name (6% Initial of Last Name 1- (40 pts) 2_ (12 pts) 3/ (1Zpts) (12 pts) Write the products of the following reactions. Be ce appropriate. Assume normal workup. Do twen rtain to specify stereochemistry if the twent -thr equestions. If you answer more than twenty questions only the first twenty will be graded. (40 pts.) 0 0 a. \6) (CH3)ZCuLi a O L O‘l/ O o e 1 4/% H + (mall .05.. 9 O H CHz—PD—{OEUZ Eli» k. 0/” + 0 (+60” O L + HCN, cat bdé’e. EtOH wivent D p14 cg mgr/0k 3%:wa l . C-CI ' O 0”” ‘ ’ OZN ~78°C CHZCH3 Li — t. NH3(|iq) / EtOH -’ % (52’0“ GHQ-CH3 ado H than HC+3 (OOH V E HNO3 / l H so4 \ 2 N0 'V 2. Write the product(s) of this reaction. Be certain to W Write the mechanism for this reaction. Be certain to show t e s ruc ure of any interme iate(s) involved. Write the kinetic rate expression for this reaction. (12 pts.) ( \ M O racflMCl CH3 3,3 (5t—-&—- 340 CH3-CH2—ijC-CQ Egg—21» év© "f .99 ‘09 /:_ E? 9 (Sting-64“ .4 {CE-CM HOQJH ~34 J” (Wow @/w ”2% Br- ide: «4 EWBFWXQ) 3. Write the mechanism for this overall reaction. Name the reaction. Name the intermediates. (11»pts.) (a e . / Ph3P-(,3;l—CH3 2% A). d + A _.___> d + PhsP—O C-H 4. Given/G/ , acetone, ethylene glycol, ethanol and any inorganic reagents B NH2 (i H 5- Given aniline O , acetic anhydride [(CHs-C—‘EOI, acetyl chloride,(CH3'C'C|) ‘ 1- As—ILL“ wf‘cf ”fig-(— {fl [op—er NIMCL‘ 9A)“ Vbzoz ’0 [ i I 2 (11pm) and any inorganic reagents you need, prepare pure /“:«'lL flc‘fl iN'Ac WC y” We 1 “’4' ‘ U Ac 6/ \ ( $03) O 6 Given benzene succinc anhydride Q0 , methyl bromide and any inorganic reagents / | lfOCA ”"l (V C a! ”6/1 Ccm/ m0 ...
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