322bs05_e1_key

322bs05_e1_key - Professor T.E. Hogen-Esch Feb. 2, Spring...

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Unformatted text preview: Professor T.E. Hogen-Esch Feb. 2, Spring 2005 Chem 322D First Progress Test Initial of'Family Name - kg; TA: Lab Time: 1. (10) 2. (10) 3. (10) 4. (30) 5. (20) 6. (20) Total (1 00) Mal/i‘p/e L'S ov M‘s avian! n + + + - Ow CM (3% CM 0% ( ) 1. (10) In each of the following give the most (M) and least (L) stable intermediate: 4» —-»o A (if )1 a. ( > (L) a (M) ( ) fl? (4611 moot 1 % (1M We!" 5% b- 6H2CH=CHCH3 (SHz-t?$4,.—CI-i2 CH36=CHCH3 (CH3)3C5 6H20H=C(CH3)2 CH3 ( ) ( ) ((L) ( ) (M) 2. (10) Indicate which of the following is aromatic (A), anti- omatic (B) or non-aromatic (C): From (0, ~L £4; {vi/4r or elm/mfzo - W /\ - O— Q Q O u :7 (A) (A) (B) (C) (R) (5) 3. (10) Write all reasonable resonance structures of: 61- c'2H2—o=CHCHZCH=CH2 <—-> QHZ=I CH CH3 3 ’3 54% 604K, 4. (30) Write the predominant reaction products. If no reaction occurs write “no rxn": l g z [L a ' . V / C>=O M1 Ho (lez)50** Lfl Q04] ‘ O 2) Hao+ H b. CHaOi CH=O inf—BE; Cflfiaac #0 (IIon . 2)H + O 3 1 tyw imam m7?» . c. 1)NaBH4 GCW 0,4 0 41/ H- ————-> Z. <_:>'C _O 2) neutralize ‘ 4" all 2) H30+ O O O\/\ I OH 0 90:11 Ow (W O f. 9 . - (x to (CH3)ZCuLi 1- H3 _» N0 Br 1 A GM 0 1%, (-c/te‘fi give stereochemistry 5. (20) Write the mechanisms (curved arrows, all intermediates. formal charges): _6. (20) a) Starting with E) and {$7 suggestasynthesis of / (fl NB 5 @ r»- gt a” b) Starting with (CH3)2CHCH20H give a synthesis of (Ci-13);? HZCHZCHQ Hs)2 HO using any other neede reagent(s). ...
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322bs05_e1_key - Professor T.E. Hogen-Esch Feb. 2, Spring...

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