Exam 3 - F2005

Exam 3 - F2005 - WU; 417‘" lg’ J“ '\ CHEM...

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Unformatted text preview: WU; 417‘" lg’ J“ '\ CHEM 2380 Exam 3 B “1 .N 7' Name Dr. S. A. Dandekar (100 points) 3 "L ‘ .9 Nevember I“. 2005 . '3 I; a _‘ “K 3 x) ' 1— I O r ' Section A: 88 oints 1. What feature is common to g meta-directing groups? A) The group is attached to the ring through a carbon atom. ,B) One or more halogen atoms are present in the group. ‘atem‘drimlyxaaachedzto thezringhasa"mall.orrwellgdeyelopedypmialpositive "' eharge. J D) The atom directly attached to th e is doubly bonded to oxygen. E) One or more oxy gen atoms are present in the group. 3. What would be the produot, K, of the following sequence of reactions? CH3 ', l CH3CHCDC1 CHJCHzflgEr Hgo“ Ben:ene N I J N K AlClj ether ’7'“ i‘ filo“) “ r I. .. I. voor ctr '- 1 I ‘31:: r ‘ W /\g/\ m “ g l J\I/ m (DA/ill . .‘r/ 11 v ) IV \/ V! CHEM 2380 Exam 3B Nov 1“. 2005 4. Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight.) A) CHJCHzCl-I3Cl B) i CH3CH2CH2CH C) cnacnzcnzcnzcn3 D) cngcngocngcn3 a) E) CH3CH2CH2CHZOH 54 Which would be the product, X, of the following reaction sequence? SOCL m m Ha -' ©4332“ . z ) zn(Hg). ) x inc), Ignul i, ;_- ~—‘ 7. ~., V: - _/ a \ ,— ©c7:© ©fir© ’ o ' U \ \ "f i. - V W. , ‘ "J N v. - " " A) W E) III ‘C) V D) II E) I 6. o Eng—EH—CHz—g-éH—cna I. 1, ‘ t. l a I r r'.'—"’ I H ‘ ' ' . What is the IUPAC name for 0 CW 7 I ;: A)\_2—Hydroxypropyl- l -phenylethyl ketone B) 5-Hydroxy-3-keto—2-phenylhexane g)"4-Oxo—5-phenyl—2-hexanol DY 5-Hydroxy-2-phenyl-3-hexanone ’m-Hydroxy—S—phenyl—4-hexanone CHEM 2380 Exam SB Nov 1", 2005' _' I 7. Which of these compeundstwmgd in'afi cnél-f'on‘fi tattle'lgvrcateétrextenvt‘f " " . » m-CHinHzQ-IziCI-‘Ig O 0' . O . El Al? V » Tamas; ‘ ‘ — = ...I 7- 0 I “"5” " j 1‘11: : . , zepczfiskul 9' -3 70:10' 533cm; CH3; . i r ; CHEM 2380 Exam BB Nov 1“. 2005 ‘ 9. Which of the following compounds would be most reactive toward electrophilic substitution? Mug NRA “Ra OH CH3 El D ‘ © © ,N‘HQD w} MHCOR F n ll Jll" V ‘ CHO no: "9043, OR 1 © © CH2, cans Q am; it! ,.v' S A) V 7 Q hfl\u¥)(\5 E) III 1 l,‘ .- C) {V (N 7 JOEJH] Loan, cola ' uto‘ LDK ’E),II . t 10. Which of the following reactions would yield benzaldehyde? f/"-\ , ~ V_ I, A) OH' ' g ‘ CgHSCI-izcl ——-6 '\_ "1., x ,. _ H20 , ' 7A ? i i ’ . heat ,- a ’ ’ 0 r3 ‘ - Qflf o \ H30+ // V ‘ 'j C5H5CH(0CH3) 2 ———6 g» /u\ _ ‘ - 1’16) (1) Liam, ether ‘ 87) /Q/)\ m C5H5COOH ———————~—>3 >3 / D - ,. (2) H20 I.-.“ D) Answers A) and B) Answers A), B), and C) 11. Simple enols are less stable than the [automatic keto forms because: A) Actually. simple enols are the M stable. ’9 B): the CC 7: bond is weaker than the C-0 1t bond. E C) fewer atoms are coplanar in the keto form. D) severe angle strain exists in the enol forms. E) the enol cannot be chiral. €er {filo V, CHEM 33 80 Exam 3B NOV 1“, 2005 12. What w0uld be a good synthesis of the following substance? 0 (allgc—©—ga+3 .A) A) (If ' (Cl-I3) 3cc1 CH3CCl f Benzene —-—fl —‘—) _ ,N AlC13 AlCl3 " O B.) I : dd a COR grow CHBCCl (C53) 2C=CH2 v90” 0‘ Benzene H —————> -' gt got} mwlw M Alc13 HF ‘ l \ A m um (20% More than one of these mum I \ ma, 3) 3|) m \O CH3CCl (CH3) 3CCl Benzene ———5 “a Al.le A1C13 None of these 13. Toluene is subjected to the action of the following reagents in the order given: (1) KMn04,OH', heat; then H30'" (2) HNOs, H2804 (3) En, FeBr3 What is the final product of this sequence? H an x ’1 " ’6 cm CO "02 i 3 av J‘Noz 8r > ‘1 no: Er \/ l u m -, Cstr 5,, ‘f/ B’ J “Dz I .7 U «x ‘_ NC: ~comm I ' lV ‘v .5 A) lII ’ "’ B) v ‘2 C) IV a! ‘ ’2‘) i1 in)" ;_ " -‘ .J)’. \r/ ‘KVV' ‘ LL". , / CHEM 2380 Exam 38 Nov 15‘, 2005 x 14. Thie following compound will: CF: 'T C) (7‘1 v ’fail to nitrate under any conditions. '8 nitrate rapidly in the ortho—para positions. C) nitrate slowly in the ortho-para positions. ,Bf nitrate rapidly in the meta position. nitrate slowly in the meta position. 15. What is the product oil—the following reaction sequence? A/“w'i Kath War 9." \ PCC : C5H5CH30H 59 ‘ CHzClz \ XL 0 ll C5H5COCH2C02E1; ‘BKC6H5CH2CH2COZEt ‘Q\ OH I ' C5H5CHOCH2C02Et “CGHSCH20CH2C02EI "7 5) OH I CSHSCHCHZ C02 Et .\ ~ 7 £- \+\:<‘>’§’OEJC' "‘9 . znér CHEM 2380 16. Which of the following would undergo racemization in base? CHSCHyI-m 5) [V .5.“ C) BothlIIandIV 111 II Exam 33 NOV 15" 2005 t)“ CHw o fifeqo l ‘ u R W ' CH,CH=I~~---i—CC.H, Q) ca . DHCHC“: cf; 0 O\ u "will 00 Qf‘ g} CH: 0 G} ‘9 CH:IH-..C| -— LIE-‘75,"; lo t ‘ x0 5 W W !\l 17. The relationship of propanone and propen-Z-ol is designated by the term: A) Resonance structures ‘ ‘ V R n '_.- B) Diastereomers L) ‘f C) Stereoisomers ;! D; Conformational isomers / '- / H. E), ' Tautomers u/ 18. Which compound would be most acidic? RA) CH3CH=CH3 A z. B.) Benzene . M, I ~ .Ci; 0 (fl; ‘ Li‘qu ._ I q Lamont) CHaCCHa ’ (z - D) CH3CH2CH3 /" 1/ ’ E) Cyclohexane Page7 CHEM 2380 Exam BB Nov 1“. 2005 19, Which reagent would best serve as the basis for a simple chemical test to distinguish between: i ii c-CH, Ic-CH, ? G W 0 Al AE(NH3)2+ /B.l. NaOI (12 in NaOH) CV), Brz/CCL: ‘6) CrO3/H2804 E) NaHC03/H20 20. Which reagent(s)’ would you use to carry out the following transformation? isopropylbenzene —-——> 2— and 4-chloro-l-isopropylbenzene A) CszCl, AlCl; B) C12, light. and heat f/\\ I la” (3) HCl, peroxides } ,3. __.; 7-; - ‘17: hm sock “fl in :l C12, FeCl3 .’ r 3 ’5 21. Which of these is the best model for the transition state of the rate-determining step in the nitration of benzene? H No, 52.5.6"... 0,»: in“ /I’ ll ', A" I ozws‘Hs‘ vx’fl H N02 .@ EVE fr~-\‘ V'JV/ /,V Aw Bi [V C) v D) m Page 8 ‘\\< CHEM 3380 Exam 3B 22. LiAlI—h (LAH) cannot be used [0 convert carboxylic acids to the cone A aldehydes because: c A}; RCOOH is reduced to RCHZOH. -. B) RCOOH is reduced to RCH}. ~ ‘ — “ " C) RCR c. H " RCOOH is converted into 0 . D1 LAH is not sufficiently reactive. ‘ E)_IRCOOH is convened into RCOOLi. v” .r L 23. Which of {he following compounds is an acetai? O D o I! II II \ cmccwcocu, 0+,on mo” k II In cfiocécrgocm /- Iv /. N V A) IV E.) I C) V II III None of these 24. Predict the major organic product of the following reaction: H20 Page 9 NOV 15‘. 2005 spending CHEM 2380 Exam 38 Nov 1", 2005 25. Only one of these reactions will produce a product which. at least in principle, can be resolved into the separate enantiomers. Which reaction is it? A) O \ e g IIL new .+7MCH3§CH3 1 ' _I ' a w '2 1|{ (“3 O ‘V OCa'ug CH3CH2C=O + BanCHzCOCzl—l5_ , :H two; embr C) T c315 t; , x CH3C=O + xs CH30H + HCO~—C’ 0W3 D) (n) H o .. _ i, \ ' ‘ CH3CHCH2COCH3 + (i_-EU)2AlH cafe—(1743:.“ “t 950% x l we, CH3 E) H _ C I A? ,» 'i ‘3" 7“ 4H L. CHM Br + c HC=O c I ,‘c ‘A . —. a 5 g s 5 q; whip) a, g; x “a” V_ x H/ . V.‘ . 26. What would you expect to be the major product obtained from the following reaction? No: Q .L» —, . nor, ‘ 3‘ so," "02 No: "02 gm 50;“ so,H Sr 573" I l H "II; no, 4" a. 30,” N A) II B) Equal amounts of II and IV C) W ‘ I E) 1* III _/ Page 10 CHEM 2380 Exam 3B Nov 1“. 3005 Section B: (12 points) I Complete ANY SIX of the following statements. filling in appropriate terms. phrases or 7‘ - short explanations. as relevant: \ and 55‘“; 535% in electrophilic \ /{‘-. A. Substituent groups affect both {'64 film; aromatic substitution reactions. ‘ ‘ afivfign,’ B. When two different groups are present on a benzene ring, the 53‘s / generally determines the outcome of an electrophilic aromatic substitution rEaction. C. A compound with an -OH and -OR group attached to the same carbon is known as a(n) hem, gaining! >// D. A compound wit/hearTOH and CN group attached to the same carbon is known as a(n) gyogobgg If} n; . r.,— E. The driving force for the Wittjg reaction is the formation of the very strong _ ‘ A I Tatte- r r Pr d in tr‘fifv‘rr‘ncd =' V 4'71 hen I mark: he 0M6 \ >1, 7%csfi‘ug‘v‘s - uxng 5”} gkes‘a‘rfififlv C'x'iétér F. 2.4-DNP is a reagent frequently used forifunctiopal group tests; it detegts the presence of gl'cuggdg/ret #:8737119: 2:0 arr-up)“ ' _,/ ;,/”””' ‘ ; / l l G. The Tollens test, used in con'unction with 2,4-DNP. can distinguish between QJCffiwcs'fiS y A; $165 . . H. Hydrogen atoms on carbons 0. to the carbonyl group in aldehydes and ketones are unusually acidic (pKn 19-20) because: i 1’; r,‘ .'}_/'".?..ll_t‘§'.5..;.L€ “1‘3. ';,-v’i.§.'_’.'-"“ 5'5 j 7-i (filf‘immwa Us .SEVIng‘K}! ' .gf' ‘ I“. "I ./ v ' J E inducing-e and (watt-"itier til—km- Page l1 ...
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Exam 3 - F2005 - WU; 417‘&amp;quot; lg’ J“ '\ CHEM...

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