Test 1 soln - J. Chem 2536 Spring 2008 Test 1 Name Pledge:...

Info iconThis preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: J. Chem 2536 Spring 2008 Test 1 Name Pledge: l have neither given nor received information on this test. 1) Show the nucleophilic aromatic substitution and product for the reaction below. Use curved arrows to show the electron movement. Show four resonance structures for the anionic intermediate. Label the nucleophilic and electrophiiic atoms. (12 pts) 2) Fill in the blank using the choices that follow each blank. (2 pts ea) The Cut”; stretch of benzene vibrates at a B (A; higher or B. lower} frequency than the C=C stretch of cylcohexene because the benzene bond D (A. has lighter atoms, B. is more polar, f... is more iike a double bond, or D. is iess like a double bond). 3} Propose a mechanism to explain the formation of the foliowing product. Do not add any reagents, use those given. (8 rats) Page 1 (B 0 “W E) \\ \CHZCHZCMZCKU Q \ O Q 11,, flip— / wattan Cuff/“L I \ "AIM-.3 \1 NO: 0 /“‘~ it a" b Chi (M2 UAZL‘ Mummy m Q ,sr. CH 1:: w \ C H 0 j “‘2: o 4) Label each compound beiow as aromatic, antiaromatic or not aromatic. (4 pts) {ANTI Ag (NW N of ,Aflo.\,\ IA ,flo M IANT Air/th 5) a._Give another resonance structure for each compound beiowr (3 pts ea) b.. Circle the compound that you wouEd expect to have a C=O stretch at a higher wavenumber. (2 pts) Pagez 17 0"” W I 4' H O ‘ M’Zowc + W "‘ J }.- a!“ (woNlhfiBoi’Q$ [93$ 9 Do,“ng [or M \ ii: O Skoc’wrfl. 4;“— eé’H’f C v ‘d ‘\Se%ne~i u~ i> ii i“ I'm-u” 1W4 dbk'dct‘xlrQ, LUV“ “\m‘ E: ‘ (- ow # w” bun-tel 6) at Activation/deactivation: Rank the foiiowing compounds from most nucleophiiic (l) to least nucieophiiic (3i (5 pts) be Directing Effects: Use arrows to point to the positionis) on each ring where an electrophiie wouEd add‘ (3 pts ea) Re, i'bo‘kfi (TU; blood «'3 miner 'i Clodbifi C.\v\3 ‘ A \i/ (a CPU?L 3 ’t 043C?" 0 L 3 i 7} a. Circie the compound that is shown in the ER beiow. b‘ tabel which bond stretches iead to absorptions in the functionai group region. (8 pts) Page3 JIM!) FKUO “:0” LN)“ 33”” “XXI 2M“) Zth) 1-H)” 2300 mm O C “:3 ‘ H N CH3C§*\LC“OH \ k ) / NO $7125.? Cu #6 MC, M—a §,TRET(I\_\~ A \ AT 22> C.» $00054“ 1% NOT 0 gm M) n (jg/(Ml -\ E LESS CHE \J\ U 'x. 0‘ :90 n - (Li lac H —-——-—LL> / *C’MOH ‘1 W” Y .m (‘1 f ' ‘3 . ’ r ,Ll 62W: M N (Lch 2 g N (0402 N u. a) 8) Give the major organic produc’ds) of the following reactions. (8 pts) 0 Lng A a ' n [3 ~ “6" 0 CH3 0 Bugs H 0--<: a; $9.;th \3 u E t [E can: K M O ' L...c H CH C W C- /' ‘N R k' n kl “x. , , mod} \ ‘M \\ / ——-——--——=> i / @‘ m c E 3 CM 5 0,61% 34 “‘\ C: E: /’ (6 ptsea) O:C..-(’.\‘\‘$ CD‘SH 1x Hzgoq {/23 flkorQ i MW mg €443 043+“ VQHJ" diredrg E} T95 C . Q f’ra . /“\ Par C L;?;"Q\A CJyxi’ Ki\fl:9 a u 0- v/ A103 SkWAcej~ acy¢m*°F A N . \ 1 —«»——--—~>> Hal}! 6 CHECRZEV Tabie of some reagents: flHHgVHCHC iWnOZ MWHO4 NBS \ ‘/ CH; *C" ’k “,4 &’ PageES 8) Provide methods and reagents necessary to prepare the foilowing products from the given starting materiai, Show products of intermediate reactions“ (5 pts) o Q; (:1 QCMK / l ming (1 SOBP‘ NH 3 flrvmoz i\ a _ ruse \ D “:310 his {32:2 N O L CeYSrE ‘ 3 sea ; “EQLMZQHS \ e We; Er " \\ Extra credit (3pts): What has potential as a "gas aitemative" because it generates “4 times more energy than is required to produce it? - i . Top of Periodic Table “’5‘ (v Q AHLQ‘“ @\ L‘L‘LM‘ 5“” ‘ H‘fi (“S5 ("r wwdpdvi I!!!“ --------------- Page6 ...
View Full Document

Page1 / 6

Test 1 soln - J. Chem 2536 Spring 2008 Test 1 Name Pledge:...

This preview shows document pages 1 - 6. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online