W06 midterm2 key

W06 midterm2 key - Organic Chemistry 30B Winter 2006 EXAM...

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Unformatted text preview: Organic Chemistry 30B Winter 2006 EXAM II, Page 1 Name I. CONCEPTS / NOMENCLATURE 1. a) (4 points) What is the single main physical feature influencing the boiling points of: ’f’ L i) Alcohols: @Mjfl~ W5 ii) Ethers: WW Mg {ll (éé/t 6Q, ”(40/4 {497% ' 45M) flu kmzcvéfiséfz/ b) (6 points) Rank the following compounds by increasing nucleophilicity and explain in 1 short sentence the origin of this difference: MeO' EtS‘ H' 7‘ 3 A B C Trend: _C_<_fl:<_§ + $ Why? [hate/5723 9‘53: 9/ moéa/QZC / no»; ‘94 64%. c) (8 points) Name the following compounds by the IUPAC convention, unambiguously specifying any stereochemistry: OMe Mm +‘/ f V ,I— c) (7 points) Illustrate the following within the context of material seen this quarter: carbocation rearrangement: fife ,7 fi 46/ oxidation: Organic Chemistry 30B Winter 2006 k EXAM 11, Page 2 ,, Name 11. REACTIONS 2. (25 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!): b) 1) MeLi H3C : ——--> H \ 3 2) \7 o 3) NaH, Etl "L 3’— 1) H2804, heat l:>—OH 2) R003H m! N} 3) PhMgBr » + §' 4) TsCl, Pyridine \) 5) NaN3, DMSO ”4;: I Q '7 Q ~7 0" 2/1 0 ’P4 1) Mg, Eth , Br 2) O Y 1" g 3 FCC ’ 0 e) 1 TsCl O HMQ OH 2; Kl H m. N o::‘ —> 3) MeNH2 I (”LU 01) Organic Chemistry 30B Winter 2006 EXAM II, Page 3 Name III. MECHANISMS 3. (20 points) Provide a complete, detailed 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 bondforming steps must be shown! a) (’ points) Ha __ Le i >< k cold HCI (gaS) >:+ : 0_ CI HO <%A11>\@ A W (’1 , 0‘30 ‘4 b) (12 points) K” H \7’ 3 \ OH OH H2804 + 77/ OL< C/ H\ @J’l + 3 H50 _. (a Organic Chemistry 303 Winter 2006 EXAM II, Page 4 IV. TRANSFORM . (10 points) Devise a reasonable synthesis for the following compound from reagents you are familiar ith 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. H—CEC—<OH _._>’ H— OMe H-CEC—<\ p‘QH/hQ—C Organic Chemistry 30B Winter 2006 EXAM II, Page 5 “9/ Name 5. (20 points) Devise a reasonable synthesis for the following compound 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. OH F, ...
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