Exam 4 Spring 2005

Exam 4 Spring 2005 - W W W Name Initial of Last Name C...

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Unformatted text preview: W W W Name Initial of Last Name C T.A.’s Name 1. ' (34 pts) 2. (6 pts) 3._________________ (5 pts) 4.______________________ (6 pts) 5. (10 pts) 6._____________________ (10 pts) 7. (10 pts) 8 (10 pts) 9 ________________________ (10 pts) Total__________________. Qfltc/l/ o [MFMC-a 1. Write the products of the following reactions. (34 pts.) 1)KOH . ———> w H a ml“ 2)CHs-tCH2')4—CH2I3V (:fikt‘m *0'4CQTIUw o 3) H2N-NH2 lEtOH A 3’ b. Cows __> (\s / CH:.,/|\I‘CH3 A MN 9.! I 9 OH . __ ‘ 04/M Met” 1 A) W: for” / \' NH 0 2 1)NaN02/HCI K __—._—_> °' 2) Cuo.Cuzo Q ‘0 H3 I “=4: 0 d. E ] NaNOz, HCI o N ———+ C 1 ,I4 rd 0 Nr’CW/ZCWCM: II ' e N—C—CHQ—CH3 ————->"'A'H4 \ l 5‘20 0 CH3 0 9 6' w‘ W( \C \\ ,w 5 6" ‘ f H C D“ My? Aim—t W HO N /Hg “0 0v! O H pH 3'5 0” 0K ) \Cu'j CH W + 0 NO N‘LL N01, 9 O H s ’ OV‘ 6 —2—> /. I NO NH3 ML / g/ NHL OH 1 OH/CO "Cr ( h. (j 1)_N_E__2.> 60 as M II 2 - , O CH3 cw} K k- E: ———>N:Zg'og"0” © #Or mmfl¢ SO39Nae 0% W Br I G CHS-CHz-fiHLie N“ fulfdg . = 1640 2301/04/ngme A 3 equivalents t: "NM NM 2»ka OH 3 20% mos . Q ________.>250 Write the products of the reaction. What property differences would you exploit to separate them? (5 pts.) 0 O 4. CH3 CH3 These quinones are found in human cells in the CHao Wk] ' hegA lad-27w 0 CH3 ( 1V0 \\ n=6to10 ofthe WV 0 m ‘7'. (6pts.) H3 5 Choosing among o-toluidine firm2 ,acetyl chloride, acetic anhydride, chlorosulfonic acid, 2-aminothiazole H2N%\I 1| S ) and any inorganic reagents you need, prepare H3 (10 pts.) NW1, 9‘ NJ,er N g i at orig-col w} 9 so—ZN 43] “z 0 . (Cdfizo 6 JOE. Cl 9 “3 Nil-8% (I? K NH2 _ 6 CHF©_C_NH2 1) Hoard?”2 , D + co, ' 2 CH3 Write the structures of at least two intermediates involved in this transformation. ; Remember an intermediate has a finite lifetime. Write the product(s) found if the read?) 1 carried out in ethanol rather than water. (10 pts.) IQ 0 ll fi/BV / )9 ' veg—mix” “‘9 C ' '1‘“ 05%“ 7, Write the product of this reaction. The analogous reaction with 2,4-dinitrobromobenzene occurs at the same rate. In no more than two sentences, what does this tell you about the mechanism of the reaction? (10 pts.) c. 0% 8. Shell Oil Company has a significant amount of benzene, propene, and butenes available from their refinery streams. To increase the value of these hydrocarbons, they have developed a process to convert these into phenol. What is the other product formed in this process if they used 2-butene and benzene? Outline the mechanism for this transformation. Be certain to clearly indicate the structure of intermediates. Be certain to clearly label the rearrangement step. '(10 pts.) fl . 0/0” 13% ’49 1 ‘ll/\ 0% 1" B-Maltose is a disaccharide. Write the structures of the a and [3 anomers and the neutral intermediate involved in their interconversion (mutorotation). a(+) maltose [oz]:5 = +168° B(+) maltose [on]:5 =+112° The maltose undergoes mutorotation to yield an equilbrium mixture whose rotation is 2 [(1105 = +136°. What is the composition ofthis mixture? (10 pts.) ,(l/f‘eruuflw 64ch ‘- Scwl [-43.6 {*jfi‘“? = 3&9 Him)" “w‘glt 'ub; ELL" 3"" @ «sow ~32 9- 303‘?“ )(3. p :1 572 craft?) 0(5- ...
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This note was uploaded on 05/07/2009 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

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Exam 4 Spring 2005 - W W W Name Initial of Last Name C...

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