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test2A2004 - CHEMISTRY'65.2263/7(2004 TEST#ZA Name mafia...

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Unformatted text preview: CHEMISTRY '65.2263/7(2004) TEST #ZA Name: . mafia, ye _ (MARKS) . , ‘ ' j y‘ 1. FOR EACH OF THE MOLECULES SHOWN BELOW, indicate which carbons are primary (1 '), secondary (2"). tertiary (3°) or quaternary (4'). ALSO PROVIDE the SYSTEMATIC NAME (or trivial name) FOR EACH MOLECULE. V'tjai/ [ISmmfg'4‘I fly, 1: SM OH 2'. o ’9 o - . Io '/ I ‘- (6.) I . Br if d4 /I V 04., / L/ V :I "’ ‘Megt “L 1‘0 , , 2. Jfi P PAR ‘L 3sfmmo"2;tl ’ ‘L‘me‘bhng’ WW M, / g MM % 0M 5 SW 5 gr 2a. PHYSICAL PROPERTIES: EXPLAIN WHY the boiling pt of n-alcohois are higher than the corresponding primary alkyi fluorides. R F ”mud, gm'L‘j, K‘- 06“ d?- d’— daupc‘i/dyfoec Guaraaodm ‘2’ » + wwwweww- I:- WI Map. b. EXPLAIN WHY t-butanol' Is miscible withg water while n-butanoi' Is only partially [M soluble. 9 -:.~— 7943025134, m,“ CH; 51:43:72» Hi 3%. SHOW THE REAGENTS NECESSARY FOR EACH REACTION: (8) e M —-——I- 'W\/\ k _ 0H Crag] H9 1 ”W" 0 CH3’L CH3 CHSJL CH3 , c H 59 *2 ”LN“ CH3- CH2- Br —a- CH3— 3 ~— CH2CH3 60+ 2 MAM/2 M ——-—I- M 3b. SHOW THE STARTING MATERIAL WHICH WOULD LEAD TO THE PRODUCTS SHOWN: (8) - WW law/~22 . ‘ A .7 or LiAIH W ”om” SWOT: —-—->-4 MN _ UH ‘ .1 M 9” , TsCl M on M ' —"'* NV 3.] QMML A075 or 5r 9—3" —< SH \/\/0H '7 ”“3 ‘2’”ij Br -—)-— 7 M ——_—_ T HIS/— ’5— C "" m CHEMISTRY ;65.2203/7(2004) , , , TEST #ZA cont'd 3c. . sH0w THE EXPECTED PRooucT oF THE FOLLOWING REACTIONS: (8) V ‘ . - . V _ ' <> :09 + <9- EM OOH; ' ' TsCl _ or, 2' W' \/\_I 52:21: \/\._. csw/ 2W ' CH3BI‘ -J-—> CHSMQEK 2 I’M-Lula 4a. ‘ Use the appropriate chemical equations to show why hydroxide‘ Ion (pKa H20 ~ 16) Is not capable of deprotonating methanol (CH3OH, pKa =16) In uantitative fashion. (4 m Mm g _ - H20 + HLo <3 on 4 H306 ® Kaela Mum + H20 :3 Mace. + H3 o€i® K42: M‘Té/MMQ, (a) ' @”’[email protected] meoH+ 681/ ?- meoe+ 11125- K: KoJ’ .-K.. /M lom./6—-IL ; /__ Mani ,- .— Ifleok aw}; W 55% 1?de 4b. MECHANISM: Draw an El mechanism for the reaction of hydroxide ion With 2-bromobutane' to give (6) two products. Show clearly the appropriate ‘ intermediate and the curly arrows for all electon flow. Which rule goV‘ems the product distribu " 3M3 ev: / m M ,m - 1‘me [369%] 1.1%) /—_/ ' + H30 /—( ‘ H 1 intermediate 9r - ImanJZ _ k // 1- H20 7. I MM 5. isomers: Draw all possible censtitutiOnal ISOmers of 1-pentanol (Cl-léCHzCHzCHzCHz-OH) (6) Indicate which' Isomers are chiral and assign the absolute configuration to the enantiomer of your ...
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