Exam1_AnswerKey

Exam1_AnswerKey - Exam 1 (Ye-1M ) March 1 t 2007 , e/ ,t

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Unformatted text preview: Exam 1 (Ye-1M ) March 1 t 2007 , e/ ,t <7henfisflo“2262.Secfi0n l Nfinufi féi}lgkojcwfii Z:‘%§£r,MMHWhWNWMUWUWnW”Ni no (first) The exam has 7 printcd pagcss ol‘qucstiom and 1 page of tables. (ffhock now to makc sun: you have all l, 1 questions; and 8 total pages. Metkc :41,er to write your name on the first page: and on the page 7 in the provided spacc. Put all onswcro on thoac ShCGtS. The exam is worth a total ol‘ 125 pcuints. Multiple Choice (4 points each, 28 points total). Circle the one BEST answer for each problem. 1. Which ofthc following compounds aromatic? ll 8 ~ //3 b' (fi\‘ 0‘ (/\ ‘Ifl’ “ ‘ Hh (m kmj () W W l) t fl 1 fiw/ winmwo (fie 2. Which is the correct lUPAC name olithc compound shown? A \ a roamino-n*z~mcth ’ltoluch—mUtrbox "lic acid, l) > k l COOH (bi) draminoflltfidimothylhcnzcnccm‘boxylic acid HgC\/L\\/CH3 . l 3 (CH—amino—Zfi-dtmcthylbcnzoic acid Kg”? V, f) learboxyfi,5~dimcthylanilinc NHZ (c) nonc oi‘thc abovc is correct 3. Which compound would producc on electrophilic aromatic substitution product upon reaction with MC l3 and acctyl chloride? cg NHQ j): l /\\ “‘33 /\\ //\ V <a> {5 MG @U m Pl <e> w // / ’/ // J 4. Circle the compound which would he the most reactive towards alkaline hydrolysis. Cfl Cl (a) E) (b) Q to) f/ N02 N02 5. Which nitrogen atom in the hctcrocyclic compound adenine is the east basic? 10 NH27 1 \ *N NH \> adenine / \N/ N 9 3 H (a) atom 1 (h) atom 3 (c) atom 7 (id) atom 9 ‘ (c) atom l0 (1‘) all have the same basicin 1 6. Which phenol has the [awest pkg? O H O H O H O H O H O H 1/ ’1: R ,JIQ?‘ ///lfj::\ O 2 f/r/J:i;\<\f/ N 7' \x‘ a j {5 ll 3 l l \\ \\7/\x N O 2 v9 03 N , K N O P \ N 02 N O 2 N O 2 N O 2 F 7. Which ofthc l‘bllcmfing resxmanw structures lsfare particularly responsible for the il'lcrcased facility {(TIWle‘ClS alkaline hydrolysié'; of"o—Chlomnitrobcnzcnc relalivc to chlomhenzene‘? a) f) a: G (n: \u 0;: ,O f”, 0&1 /O CNN/O N ONN O W Cl CI l l Cl é‘xwk/ %‘ C E\OH OH g \OH } A‘ B: C all fOur (731.“ w W G /, ~\ / structures OH . V f A B c (EN E F U/ 8. Draw a Structure for the ma'or 0r mduct 5 0f each of the fbllowing reactiuns, or write NR. for no reaction, if applicable. Place 0an one appmprlmc structure in each of the l4 boxes and assume Only monoadditions 0r monosubstlmtions (4 paints each, 56 points total}: \_..\ NBS / \Cl peroxides AICIB l ,/ ; terf~C4H90K I 65/ 3 ~ »» W W» " I * 1 LN r I y W mmtmmwlql_ (Div/CH3 HNO3 W646?» , a 32:39:, gw, f Nag“ 0 CH3 0 £ wor gm; ......... ,_ O m A’ 2* 5 N O t 53:2, 6/ l J 2 i x” L ‘ 8 r2 ,. SO 5 (wig? ax Hi, MMMMMM A4,. I ._ t \Vflk“ F881} ‘w/ H2504 MWWMN M\ m o CHgCHZCHZCX <\ / \ //"*</ M OCH3 A103 i Q ‘ NH2 1) HBF4 NaNOZ / HC! ‘ , . » AV C 2) pyrolySIs « o °o “ " I w i \I 1~ «i *) "Pyrolysis" means heating of dry compound 9. (11 points) Draw a stepwise detaiied armw—pushing mechanism for the i'blhjmirlg reactiun: «a mag /-:::KYJ~V/ E \J 1+ \Nk/«xk/Ci W.WWWMMMWWM,” "J + HCI ‘~\% Ray (23) meation ofthe electmphilc (3 paints) @1063 X § w y , w ‘WW” “W”? \/ V ' fAméqeieé ,M » M W71 WWW IL/éw “mg/V “W”, (d) Aromatization to form the product (2 points) A? ‘ .,,, “w” m: Pg My u + , My, ‘ 4. w: v M \V W ; (:5 «w M 61% (33} 0M x v H (W ,Qg, (C) Regeneration Ofthe catalyst and formation ()l‘I—ICI (.2 points) 6: E H 06;“ 1“ (gag WW”? M (:6; “4”” M U3 1,0. (20 points) D0 two of the {011(3ng f/Ir‘zm synthetsas sim‘tm {mm [gagging or (91%;ng any other 1mmcafunciion2,1} mgzmic compcmndlflgggwgggbggggggj«ng and any tame-r mac:de inorganic magenta, ONLY TWO OF VINE SYNTPI‘ESES W ILL BE (fHQADEiD so CLEARID‘I’ LAB EL WI~IIC§H ONES YOU WANT (3 R A D RD . C} \K {flit F , I}. (18 points total} The IR, and 1161 NMR for Compound X oi’moleculm fibrmula (776H1202 if; Shawn below (whim (3? IR and NMR dam an: attached, an the back m’thc exam), (3) {Rimming} the ( . r) for this; compogmL Slmw your W'mjk. (2 points). (AV-+1“ “31:” V2) .2 )6 C; “(32 m“ l mM / (ii) Clearly label on the, R spectrum Sli‘G/(‘lllfig f‘rcqumxcicra with the: funcm‘ma! group they represent (3 paints). (iii) Draw the Structure 0f this compound in the box at the bottom of the page (3 points). (iv) Clearly label each type: ofpmtons a, and b ( ‘1 point each) an yam progosed ytt‘ucmre. R 7 (y 5 4 3 2 i (J 5 (ppm) Compound X: b a y CH5 MW “"NQCQfl CW3 6 ...
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This note was uploaded on 04/21/2008 for the course CHEM 2262 taught by Professor Smith during the Spring '08 term at LSU.

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Exam1_AnswerKey - Exam 1 (Ye-1M ) March 1 t 2007 , e/ ,t

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