118CSpr11MT1Key

118CSpr11MT1Key - racemic Assume all reagents listed are...

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Unformatted text preview: racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reacfion’. 0 0 . H H, 20° C N o 0 0 1) P (trace), 3:2 I a Lo 2) NaOH Br on 3) H30" Lass) WP“) D) NH2 Bra, NaOH, heat M N NHL 0 o QM 1) (CH3)2CHCH2MgBr, ether OCH CH I x I E) W 2 3 2) H3O+ \\ /\ ZPTB 9a» kelewa ° 0 /\/U\ DIBAL, -60°C, toluene 3k F) OH EN H 2. Reactions: (12 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct relative stereochemistry, if the reaction is racemic indicate this by either drawing both enantiomers or drawing one and writing racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. ' o 0 1) PBr3 , /\ A) OH 2) NH(CH2CH3)2 K C) B) o o NH3, Heat 4/] HoWOH _—_" \O H 0113:, ch03 _, - 3. Vocabulary: (13 pts) Fill in the blanks with the appropriate vocabulary word. If multiple boldfaced words are given circle the correct word. A) An amide / ester / @s more reactive with nucleophiles due to increased / @esonance of the leaving group with the carbonyl. B) The pKa of a typical carboxylic acid is about ‘{ "5 while a typical amine is about 35" 70 . C) Ketones are most easily distinguished fiom esters by comparing their 1H NMR/ m D) Waxes, triglycerides and phospholipids are examples of what organic fimctional group? Ester B) What functional group gets priority in naming / aldehyde / alkene. F) Conversion of an ester to a carboxylic acid is called H 31:! ml in g and occurs by an [him ' El {m i MEQM mechanism. It is best catalyzed with acid / base / no catalyst. G) The common name for HCOO- is a E armai'éz Farm 1' i group. H) The molecular mass of a molecule with a single nitrogen is usually even /@ I) @/ False Mass spectrometry allows us to identify the presence of an acid by a molecule’s fragmentation pattern. 4. Mechanism: (17 pts.). Show a detailed reaction mechanism for the following reaction. Include the structure of the expected products and appropriate stereochemistry for all steps. Assume all reagents are in excess. 0 H2804,CH30H ML 12?? ocuzcn3 heat fl we} so; H~HSO¢1 @figw ® 0/” /\/\Ko/\ 23 7 0CH2CH3 22 /\j\f0;Q§H2C}/; @ (warm CH3 GfH 7- , 120 A u AQ’ [email protected] ‘1]! :1/ a/Ue erg; @ 09 0/6 1 5 ‘CH H2507 C’éCHZOH CH3CH10H/ 3 @ Z (Wyo CHQC‘UVfi’) U than 4;, lm‘nahov‘ H A) The name of the mechanism used in this reaction is . a) B) This kind of reaction is generally called a Tm MKSlfnRCefi c7\ reaction. CU 5. Synthesis: (16 pts) Show how you would carry out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. You may use any inorganic reagents you need and organic reagents of five or less carbons. 6. Acids and Bases: (8 pts). Circle the compound in each of the given pairs of molecules that is more L’ ' e boldface H. 7. Nomenclature: (8 pts.) Provide the systematic names or structure of each of the following compounds include E/Z or R/S Where relevant. O i>t~oP~1l S'mell‘vl-‘I‘fonoalt A) S‘m{-\.thN3(J+“€YlOarit Q q I O C! 3 — e‘n’wl— ’7’ -melhylcyclo Pen‘l‘anecqunnv/ B) Q chlana'fi B NH r 2 CN 5" (Amino ~7-‘loromov Li'Pf‘OWiOCi’Qh y'irii't C) r... 04AM Gm; D) N,N-diethyl-Z-methyl-3—aminocycloheptanecarboxamide 8. Spectroscopy: (20 pts.) The unknown compound A (ClongNzoz) gives the following proton and carbon NMR spectra. Significant IR peaks were also observed. What is compound A? 6" 200 150 100 ' 50 0 .. CHZ-CH2-— «PM a) 5;!" CHLfcflsz 3 «RH 99% 62cm 7. I Ig’ mRU§Wc§WL (stack, wkod‘Piec 15; no SMc’HN grade. («baled “Pfiecanfi’ gnu/“Mew 7 a; 3" Conhahs Lxgmfi‘ Comfl\ ...
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This note was uploaded on 02/05/2012 for the course CHEM CHEM 118C taught by Professor Nambia during the Spring '09 term at UC Davis.

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118CSpr11MT1Key - racemic Assume all reagents listed are...

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