F06 midterm2 key

F06 midterm2 key - Organic Chemistry 30B Fall 2006 EXAM II,...

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Unformatted text preview: Organic Chemistry 30B Fall 2006 EXAM II, Page 1 .1 - Name I. CONCEPTS / NOMENCLATURE 1. a) (4 points) Give an example of an excellent nucleophile and explain what factor gives it its nucleophilicity (no more than one short sentence please!): 69 6/ m I W3 V [0‘41 [Q0 / 49/577533} may “5 fl“ Xijfaue b) (6 points) Rank the following compounds by increasing basicily and give a short explanation for the difference: t-BuO‘ H” M90— 65 A B C Trend: m<fl<i Why: 3% 0&7 M/wké C fl 8 — *fiog Skuwé #‘wcéé/af, 6:55’ W Mam/60’ c) (8 points) Name the following compounds by the IUPAC convention, unambiguously specifying any stereochemistry: 3 i M VAL/\OH OMe ‘3‘ka _ Lac pkg/£039 —3 “WWW (fSolpadLfié c) (7 points) Illustrate by an example the following terms seen in material covered this quarter: Ylide: G; K 69 : P" CH; W 3 ’— CH1 / / rotectlon. ’ H oH’ A A Organic Chemistry 30B Fall 2006 W i EXAM II, Page 2 — Name II. 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!): Q/ 1) PBr3 2) EtONa OH —-—> 3) R003H Q m 0012/ a) 4) MeOH, H+ 5) FCC b) 1) EtLi , 9m 2) H2804, heat 0; O ’ 3) R003H r t i 4) MeSNa 1 0 5) NaH, Mel “ c) 1) 2 e . PCC /l\/\ 2) 1 e2. HOCHZCHZOH PL C HO H+, 'ldh t' HO/\/\/0H —-—-————>ml eamg T1 3) PhMgBr '9an 1) 0804 then NaHSOa 2) Cr03, H2804 __. CH3 6,, 3) 2 eq MeMgBr 4) H+ o d) 1) NaH, TsCI 2 KOt-B V\ ) u ’ ‘ 3) RCOsH 4) PhZCULl OIIIII I Organic Chemistry 303 Fall 2006 % EXAM II, Page 3 . W '- Name 111.} 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) ( oints) @ ‘ 8 O Wit—cal 1‘ + Ph3P=CH2 69 9,. t /’ Pflj 3 0 ' ———~>2 - *7 b) (12 points) 005,03 M OH a. H230; MeO OMe CH2 mild heat @ K I WW a H 0/ /‘ Car W) W?“ I \ H O a) ( Ls at MM) écgm I H wH H V H 9 W9 ( -t l Hem: 1g M291;8\H H55: : ' 1' Organic Chemistry 303 Fall 2006 EXAM II, Page 4 IV. TRANSFORM 4. (15 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. Name Organic Chemistry 30B Fall 2006 W . EXAM 11, Page 5 ~ % 5. (15 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. ...
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This test prep was uploaded on 04/05/2008 for the course CHEM 30B taught by Professor Rubin during the Fall '05 term at UCLA.

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