30B_S05_midterm1_ak - Organic Chemistry 30B Winter 2005...

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Unformatted text preview: Organic Chemistry 30B Winter 2005 # EXAM I, Page 1 , Name 1. IR SPECTROSCOPY ‘ 1. (15 points) A compound with molecular formula C4H4O2 has the following IR spectrum. Its structure contains two identical functional groups. Provide its structure and assign tw_o IR- absorption bands of the IR spectrum: (Assign here _0_r on the spectrum) 2760'3900'. $gfi—fl S47. (7&0: C30 815' ( (PM. a?! (gr/32 Compound C4H402 (use as many lines as necessary) Degree of unsaturation: ; IR spectrum (neat liquid): Ion (3W5) 7’ “WIFE“! Organic Chemistry 30B Winter 2005 k EXAM I, Page 2 Name II. REACTIONS 2. (15 points) Draw the major product for the following reactions (if there are several enantiomers or diastereomers formed, show only one, but pay attention to stereochemistry where needed!): +4 a) ‘9 CS; 1) RC03H { ‘ 2) NaSEt "(I SET-6 \ a"; [M/ 4m yet/ca O» W) Eé Meo c“ C H; 1) MeOH, H+ J; 5” 2) NaH, Etl O 66 Eé $ Mao ~‘ ch; /7 s O H 56 - H D ) c H \ xs. Cr03, H2304 Coo H Q, [>—CH2OH ——-————————-—> \ o r + 3’ '0" k0"; r7 (-3 _, ' Organic Chemistry 30B Winter 2005 EXAM I, Page 3 (I 3%769 Name 3. (20 points) Draw the major product for the following reactions (if there are several enantiomers or diastereomers formed, show only one, but pay attention to stereochemistry where needed!): a) 1) BI'2, H20 —-———'> 2) NaOH 3) MeMgBr C1» 1) RC03H ——-———> 2) LiA|H4 3) NaH, Mel \5 \ (969 Y 1)HBr 2) Et0H(heat) \/ ‘9 s, X“ «DD/M Er m (l27\ b) /7 e) / OH 1)TsC|, Pyridine 5-— S 1‘ 3 ————> \Ll 1.} $02 SH ,7 0L (mmL CW) Organic Chemistry 30B Winter 2005 EXAM I, Page 4 Name III. MECHANISMS 4. (25 points) Provide a complete, degiled mechanism with curved arrow formalism for the following reactions. Each step must me explicitly written down, i.e. every attack of reagent, bond breaking and bond forming steps must be shown! g? -— O - —e a) (15 points) u; S h . . dil. H2304 OH __> M” QCH b) (10 points) +3 H306, O has AeONa 2) CH3| ----- "OH Organic Chemistry 30B Winter 2005 EXAM I, Page 5 Name IV. TRANSFORM 5. (25 points) Devise a reasonable synthesis for each of the following compounds from reagents you are familiar with and the starting materials provided: Note: do no “invent” new reagents or reactions. Use only those specifically taught in class or previous quarter’s reactions. There should not be more than 10 steps necessary in these syntheses, although longer ones may also be correct. a) (10 points) x M M/ j EcosHm 0” at H9 b) (15 points) u" IIII I —_-* -.,, HO‘“ :: ’CH 20H NC "’CH2 SMe é-D He SiCé 1" z I WE 5‘3” 1"" Ho “WOW Orson; [ 75d panda“, L I...
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