2005 PracMD2 Key - I Chem 118C SSI 2005 Sample Test-II...

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Unformatted text preview: I. Chem 118C / SSI / 2005 / Sample Test-II / Nambiar Draw the structure of the expected organic product (s) formed in the following reactions. Unless mentioned otherwise, you can assume that all reagents are present in excess. If no reaction occurs. write "No Reaction". 1. B I h :6 H 1. C6H5-CH2-CH3 {2 v Cg H56 H a? 2. NaOH .N CN; 2. L'A .. 2) R—CHzBr l a I 1H4 A ~— 6 H3 6‘3"” H; 3. H20 1. CH I =Ol- ‘4? IV :3”; 3) CH3-CH2-CH2—NH—CH3 3 0+3 ‘6“ L" ( 23 2. AggO / H20 / A OH H (CH3CO)2O (1 eq) IH20 I A ' p .' 4) . H w 6 NH2. .. 5) © 1. NaNH2/NH3 1:0] 1. Lg CH3 . “3 3. 1. NaOCH3 / CH30H - .96 H 6) CH3COOCH3 e” «— J~C H 3 i 2. H+IH20 J 5% S-CH f I SfW 7) / 3 l. n-Butyl Lithium / CH2 \S-CH3 2. R-CHz-Br ll. . Show detailed reaction mechanisms for the following reactions. showing the structure of the expected major product. OH 1. NaOH 1. ___ £3) 2. CH2=CH-CH2Br . 3. A o my a /)_ sz/Hht —————?— 1:07 -r H30 1 a H H / _ H 35%: H 2 C) H \ (—— at / I III. ‘ f. Show how you would carry out the following transformations 'showing the gagents' you would use in each step and the structure of the intermediate products formed. 1. ME»; 4 filial—6’3 @Hrfifif 3/ MW DAWHH __ _, . Amer—W fl CH3 GM W (9 5‘ D‘ H R-CHz-CHz-NH-CO-C6H5 / 1/11, 2. CH30~CO—(CH2)5-CO-OCH3 J/ (“3(5on 0 W3 , ‘9 IV. _ , Provide a systematic name or draw the structure as appropriate for the following compounds. 1- O—NH—CH3 IV" Z/éfw‘wfi 2. N-Mcthyl cthanamide (3' H} ' a? N H 3 . .‘ W/mw‘ 3. C6H5-CH2-CH2-N(CH3)2 N, 4/, OK‘ 0? M M g ,_. fl 4. m—Nitrophcnyl ethanoate 0 A V. n Rank the following compounds in decreasing order of basicity; . NH2 NH2 NHCOCH3 OH OH ' N 02 C O O H A B C D E F JDHéCEF‘ High Basicity Scale Low NMR spectrum shown bands at 3450, 1725 and 1640 cm'l. Upon heating with 6M ave one mole of compound B (C7H3NBr) and one f compound C (C3H502). Deduce the structures of compounds A, B & C. a?“ x 'I ~ 73/%} . >5 ‘ TMS VI. An unknown compound A (C10H120NBr) gave the proton below. IR spectrum showed aqueous HCl a mole of compound A g mole o Cmm‘cal shins (ppm) x I o I (fl " ' 1 1 “f‘” t : “9“5 4;...“ m E E .——c-H : : : ’ 2 . 1 X-O.N.ha|oqon :- C ...
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2005 PracMD2 Key - I Chem 118C SSI 2005 Sample Test-II...

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