C201HF07T1 - C10 l H i=0?Tl 1. Simvastatin, (Zocor®),...

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Unformatted text preview: C10 l H i=0?Tl 1. Simvastatin, (Zocor®), C25H3505, shown below, is an example of a “statin”, a class of compounds that lowers serum cholesterol. Indicate the number of spa carbons, sp2 carbons, sp3 oxygens, and sp1 oxygens in simvastatin. None of the above 2. Carteolol, a B-blocker used to treat glaucoma, has which amongst its functional groups? For purposes of this question, focus only on the portion of the molecule inside the dashed box. )( carboxylic acid, 2° amine, ether . 3° alcohol, ether, 2" amine c. 2" alcohol, ether, 3° amine )1? 3° alcohol, ether, 3" amine (c) 2° alcohol, ether, 2° amine C I ‘/ 3. Which of the following would be expected to have a net (ie, a non-zero) dipole moment? I c, ,p: or £3ng 6r H I. —-‘-—3” a. '\ U 4|- “ 1. CHCI3 11. BF; 5? gr cugocu, Means—1,2-dibmmoethene a = a; H ‘F ’ 8|, @1, II b. 11, III c. 11, IV d. 1, III e. III, IV 4. There are four constitutional isomers of C3H9N. Of these, how may are 1°, 2°, and 3° amines, respectively? 1" o my (a I 2° A - 1” \/ pN, @ A LN”; 1° ' ' _ ...‘ _. 3 Q 5. What kind of molecular orbital results when the two atomic orbitals shown below interact in the planner indicated? as @o“ 0.1: d.1t* O w H EC‘C/ RWe H 6. Which atomic orbitals overlap to create the bond between the I indicated carbons? What is the expected C-C-H bond angle that CHBCHZCECC=CH2 includes the indicated carbons? T T . t a is a yspaspz , 109.5“ @sp-spz, 120° c. Sp-sz, 180° ,di'sp-spz, 180° ,e.’sp3-sp2 , 90° 7. Provide the IUPAC name for the compound in the box. 2-ethenyl-4—methy1pentane cis—3,S-dimethylhexene 3 -isobutyl-1 -butene d. 2,4-dimethyl-5—hexene @ 3,5-dimethy1-lnhexene PET!” 8. How many of the following structures are n_ot the same compound as that shown in the previous question? In other words, how many of the following structures would have a different IUPAC name than the compound shown in the prior question? ( ac,— diml’hll- rum; 'g’s .diwfiql 3.9- awflmfl‘ I-hcuw, - - @0 b. l c. 2 d. 3 e. 5 ‘ "-“"-Mr-t 4;) d-‘mr'fi'r'r i- 9. Rank the following in order of decreasing basicity (from strongest to weakest base). b. H > IV > III > I u c. III > IV > I > 11 CH3CO' CH3OH 'NHZ CH3(CH2)5O' d. 11 > 1> IV > [[1 ,1 I Li Z \ @wne of the above ' 10. Which one of the following is a correct IUPAC name? i X .. . I /"~ x“, I" l x A. Q 3,3-dnodooctane / -- AV, K (a, _, f b. S-ethyl-Z-methylhexane I - I c. l-bromo-4-pentanol 1 {fir K 1’ l" ‘9 d. 3-isopropyloctane V"'\/ e. 2-methy1-MN-dimethyl—4—hexanamine 11. Rank the following from highest to lowest expected boiling point. I 1 H n m S I;—\L_< v Tm; \/0/‘\)\/ on a.111>V>11>IV>l b.IV>I>V>II>I]I c.I>IV>II:>V>III Qy>v>wbfl>fll eV>I>W>H>fiL 12. In the reaction of AlCl; with (CH3);0, which is a Lewis acid, which is a Lewis base? 0 0an In the reaction of CH3C0H with H3O+, which is a Bronsted-Lowry (B-L) acid and which is a B-L base? ‘9‘“ - Ira-mm- “mm 61mm 51mm 13. How many of the following structures should bear a positive charge? '5-(C1ND: »1 twink -1 H H\é/H H\ /H H‘\'é/H , /H \6/ q-[usk— o l B -C\ H / \ l H l 4r(2+33=*i H H ab @1 c.2 d.3 e.4 H q- (2+1\=o 14. Which of the following represents the least stable conformation of 3,3-dimethylhefine with respect to rotation about the C3-C4 bond? (ie, C3 in front). Me = methyl; Et = ethyl; Pr = propyl . . c. . 1' 3 HR 2‘ Et MaH ‘1’ a @ e H Pr H PT Q EJ‘ q Pr Me Me t 6 Me Me Pr Me Pr H H Me 13: H H Me H MR 9' 15. What's the molecular formula of a hydrocarbon that contains 9 carbon atoms, a ring, a double bond and atnple bond? Capt“) - g : Car}le a. CgHs Cngo @3911]: CQHH e. Cngfi 16. Consider the conformational energy diagram of butane with respect to rotation about the CrC; bond. Which of the following bond rotations would produce a similar looking conformational energy diagram in terms of its general contour (and not necessarily the specific energy values)? ‘ f f { t J I .15 x butane (CFC?) ea: - L“ a C" "r ‘C T H % ethane (C1-C2) *7 I \ " i h m‘l M pf propane (C1-C1) ‘ « . g I; ( 1-bromopropane (C1-C1) - C" (1"(7' pl! l ‘ If 8? h t la c . I; _ chloroethane (C1-C1) {1} -(g E54: . P \Q ' I Li I i H 04.354 17. How many carbon atoms lie in the same plane at all times in the following molecule? a. 6 b. 7 6 8 d. 9 e. 10 or more GHQ: _ ; C: flag CH3 2 For each of the following pairs of structures, indicate if they are: a. the same compound (which includes different conformations of the same compound) b. constitutional isomers c. sis-tram or BIZ isomers d. difierent compounds that are not isomers Note that each question has a single answer, however answer choices may be repeated between questions. Cong/l5 - (:1 (:1 CU? 8' r is ('2 ('3 °‘ ' \\“‘ ® W \ F a (i "l FBI! leI Fell Br F12 ,C .C 4: “K CH3 9" 19. W __ HSC CH3 lrfins " .. Tn” ' 20. C(CH CH3)4 \Sg/ 23. The most stable conformation of cis—1-isopropyl-Z-methylcyclohexane is a chair with: a. both substituents equatorial b. the methyl equatorial and the isopropyl axial @the methyl axial and the isopropyl equatorial d. both substituents axial 24. Which is the best Lewis structure for N03“? /a’, :..:e b. :..:e _...e D _.._e _/o H /o 9% ./0. /d/.0. //0 §=N g—N :ii—NG) :(j—N: §=N .39 o .2 , _ y i I - V: 2‘4 9/»? so [Ml #l in}; ,— , fn+q\:-H 25. For which of the following structures does the concept of cis/trans or BIZ n_ot apply? CH3 2:” / ® CH I CH % 3 WV 1‘\]/l\/\/‘\/ 2‘ a CF3 . I B. I, III C. II D. 11, IV hile the question can be answered correctly, none of the answer choices provided (in other words, none of the choices A, B, C, or D) are correct. 26. Which will have a higher percentage of the diequatorial-substituted chair conformer as compared with its own diaxial-substituted chair conformer: cis-l-isopropyl-3 -rnethylcyclohexane or trans-1,4- dimethylcyclohexane? @cis-1-isopropyl-3-methylcyclohexane m m b. trams-l ,4-dimethylcyclohexane c. not enough information is provided to answer the question Provide the IUPAC name for the following compounds. 2?. fly] - flith-oro ‘ Z ‘ bowl/‘0‘ 4,4-dichloro—2-butanol b. 3,3-dichloro-2-methyl-l-propanol C1 or 0H c. 1 ,1-dichloro-3 -butanol d. 1,1-dichloro-3 ~methyl-3 -propanol C] I e. none of the above ,6 (Eyfi-bromo-1,4-difluoro-2,4-dimethyl-3-isopropyl-2-hexene ® (E}-6-bromo- 1 ,4-difluoro-3 -isopr0pyl-2,4-dimethyl-2—hexene (Z)-6-bromo- l ,4-difluoro-3-isopropyl-2,4-dimethyl-2-hexene ' d’ (Z)-6-bromo-1,4—difluoro-2,4-dimethyl-3~isopropyl-2-hexene ‘ e none of the above E - C bans—1,4.d,guam _ v 29. a. N-methyl-S-sec-butylcycloheptenylamine b. N—methyl-N—cyclohexane-4-isobutylarnine c. 4-sec-butyl-N-methylcycloheptanamine d. 44isopropyl-N—methylcycloheptanamine @ 4-isobutyl-N—methylcycloheptanamine Lf—{obmfil - N’ "Mull aim-WWWM Your Answer( 1- 50): BEADBBEAEA DCBECDCAAA ADCCEAABE Correct Answer : ..D.....C. . . . . . . . . . . . . . . . . . H ...
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This note was uploaded on 11/05/2011 for the course CHM 201 taught by Professor Colonna during the Fall '08 term at University of Miami.

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C201HF07T1 - C10 l H i=0?Tl 1. Simvastatin, (Zocor®),...

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