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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 —9 Lo 2) NaOH Br on 3) H30" Lees) UP“) D) NH2 Bra, NaOH, heat M N NHL 0 o QM 1) (CH3)2CHCH2MgBr, ether \r OCH CH I x I E) W 2 3 2) H3O+ \\ /\ ZPTB Que kelewa ° 0 /\/U\ DIBAL, -60°C, toluene ik 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 , )fi/‘KN /\ A) OH 2) NH(CH2CH3)2 K C) B) o o NH3, Heat A 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 xsi g and occurs by an 015M [itch ' El {m i MEQM mechanism. It is best catalyzed with acid / base I. 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 22?? ocuzcn3 heat fl W) "O.” H~HSO¢1 621;” ® 0/” /\/\Ko/\ 23 7 0CH2CH3 22 /\j\f0;Q§H2C}/; @ CHaoH 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 (+9090 CHQC‘UVfi’) 0 Mt” than ”El immbm H A) The name of the mechanism used in this reaction is WW . ® B) This kind of reaction is generally called a Tm MKSEHRCJ 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 1n each of the given pairs of 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) WON me‘ S‘m{-\.thN3(J+“€YlOarit Q q z 0 Cl 3- ethyl— ‘1’ Math, cyclopen‘l‘anqurknnv/ B) Q CH Ianaa Br NH 2 CN 5- amino~7‘loromo't'bpr‘opfloci'th-[wyl't C) F“ 04AM SW. 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 IR:v2957,2254,1732,1210andfingerprintcm‘l. bat: 3 ® ' .. CHZ-CH2-— Q‘Pfi «PM 5) 5;!" CHLfcflsz 3- *yor’ 99% 62cm 7. I Ig’ och/“show (brook, wkq+Picc 15; no SMc’HN grade. («baled “Pfiecanfi’ Dem/“kw 7 a; 3" Conhahs Lxgmfi‘ Comfi\ ...
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