Exam 1-2006 - Test Form D Hour Exam One: ORGANIC CHEMISTRY...

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Unformatted text preview: Test Form D Hour Exam One: ORGANIC CHEMISTRY I Name: Chapters 1,2 & 4 FALL - 2004 September 29, 2004 I. Multiple Choice: (90 Points) 1. Which compound is an ester? 0 o 0 l “‘1‘” é I °1 I II Ill 0 ll C—H C1 DH] OH IV V A)I B)II (3)111 D)IV E)V 2. How many 2p atomic orbitals from boron must be mixed with a 25 atomic orbital to yield the bonding hybrid atornic orbitals in BFs‘? A)1B)2 C)3 D)4 E)S 3. Which structure represents the most stable conformation ofc_is-1,4-di-fl- butylcyclohexane? MCI-1333 ca:th 132:7 “CHM M (CH3J3E: (c H3)3C M (cash: I I? ill cceH333 4‘ th(l:H3)3 (CH3J3C‘W— C(CH313 IV v A)I B)11 (1)111 D)IV E)V 4. Based on VSEPR theory, which of the following would have a trigonal planar shape? A) (CH3)3N B) HCN C) NHI’ D) CH? E) CH3+ Page 1 5. Which compound is not an isomer of the others? CHJCH=CHEH E W M 0H 0 0H 0 I II III N A) I B) 1] C) 111 D) IV E) Aflof the above are isomers of each other. 6. Which of the following is a set of constitutional isomers? CH3 CH Br CH /J\/‘\ l (L 2 Br CH:5 HCHQBr (II-i3 P40142014} 3 GRETCHQBI“ CH5 1 II III N A)Iand]] B)Hanle C) I,11,a.nd]II D) 11,111,de E) I,]]T,andIV 7. Which structure(5) contajn(s) an oxygen that bears a formal charge of +1? ‘? H—C : O=C~—-O: CHawo—H CHrO—‘CHQ K | i : O: H CH3 I II III IV A)landfl B)n1andIv onI mn E)IandV 8. What is the common name for this compound? CH3 | CH3CHCHzBr A) Isobutyl bromide B) m-Butyl bromide C) Butyl bromide D) m—Butyl bromide E) Bromo—fl-butane Page 2 0: i C ../ 1.. :0 O: 9. Which compound is a secondary amine? CHg—N-“CHg A) CH3€H2CH2NHz D) ' CH3 CH3 CHCH3 CHgCHZCI-EJI-Iz B) | E) 1 MHz CH3 CH3 CHzNE-I C) | CH3 10. Cis-trans isomerism is possible only in the case of: A) CH2=CBI2 B) CH2:CHBI' C) BrCH=CHBr D) Br2C=CHBr E) Br2C=CBI 11. Which of the following structures represents bicyclo[3.2.1]octane? I II 131 IV V A)IB)II C)]]ID)FV E)V {2. Which conformation represents the most stable conformation of cis—l-teLt—butyl-tl- methylcyclohexane? I—Bu 1'3" was rill?" 1'3" ‘42:? I CH3 II CH5 III CH3 Hem/tau Amer-Bu IV v A)I B)Il (2)111 D)IV E)V [3. Select the reagents necessary to convert 3—bromohexane into hexane. A) Zn,HaO+ B) CuI C) H20 D) H30+ E) OH’ Page 3 14. Which principle(s) or rule must be used to determine the correct electronic configuration for carbon in its ground state? A) Aufbau Principle D) (A) and (B) only B) Hund's Rule B) All three C) Pauli Exclusion Principle 15. Many organic compounds contain more than one functional group. Which of the following is both an alcohol and a ketone? OCH3 O f 0 H 0 g A) CH3€H B) E C) I D) II E) HCCCI—I3 a men HOCHg c=o H0CH2CCH3 H OH o 16. The most stable conformation of 1,2-diphenylethane is: H H H H 5 5 CEHS C H H C H H C H H 6 5 H b 5 H s o H I II III H H CeHs H C6 5 HQCEHS H “‘3 H H H H 6 S H N V A)I B)]1 C)III D)IV E)V [7. Which compound is a tertiary alcohol? CH‘OH 9H3 CH3 . “ac-w (M 6 CH3 I II I11 OCH; Ho CH3 n: v A)I B)I[ C)HI D)rv E)V Page 4 13. Which of the following is a correct name which corresponds to the common name @- pentyl alcohol? A) 2,2-DimethyI-l-pr0panol D) 3-Methy1—I-butanol B) 2—ELhyl-2-propanol E) Methyl te_rt-buta.nol C) 2-Methy1—2-butanol CH3 | CH3 CH2 CH2CHCHCH3 I 19. An IUPAC name for CHCHa is: 1 CH2 I CH3 A) 5-Methyl-4-(1-methylpropy1)hexane D) 3-Methyl-4-(l-methy1ethyl)heptane B) 2-Methyl-3-(1~methylpropyl)hexane E) S—Methyl—4-(1-methylethyl)heptane C) 2-Methyl-3-(2—methylpropy1)hexane 20. Select the most electronegative element. A)H B)0 C)N D)B E)C 21. The sflongfl of attractive forces is which type? A) van der Waals D) Cation-anion B) Ion-dipole E) Hydrogen bonds C) Dipole-dipole 22. Which cornpound is an aldehyde? 0 O O I II III 0 0!-” Om) IV V A)I B)H C)l[1 D)IV E)V Page 5 23. g's-lfl—Dibromocyclohexane is represented by structure(s): A)! B) H C) DI D) HandIII E) IandH 24. The reaction of the Na salt of 3-methyl-1-pentyne with 1-hromo-3-methylbutane produces which of these? A) 3,3-dimethyl4-nonyne D) 3,7-dimethyI-4-nonyne B) 2,?-dimethyl-4-nonyne E) 3,7-dirnethyl-5-nonyne C) 3,8-dimethyl-S-nonyne 25. Which molecule would you expect to have no dipole moment (i.e., u = 0 D)? F H F E' \ x' ‘t r’ A) CI-IFs B) KHI“ C) :NF3 D) XC=C\ E) CPIng H E‘ H H H | 26. The carbon-carbon bond in CH3 (3:0 results from the overlap of which orbitals (in the 2 1 order C1, C2)? A) sp——sp2 B) srsp3 C) spZ—sp2 D) sz—sp3 E) sp3—sp3 27. Which of these is the weakest of the intermolecular attractive forces? A) Ion-ion D) Covalent bonding B) van der Waals E) Hydrogen bonding C) Dipole-dipole 28. Which of the structures below is not expected to contribute to the C02 resonance hybrid? + — - + — ++ — — + A) o=c—o B) 0—C=0 C) 030:0 13) 0—0—0 E) 0—020 Page 6 H. 29. Identify the atomic orbitals in the GO sigma bond in ethyne. A) (2592:2519) B) (23193325133) C) (ZSPsZSP) D) (213,213) E) (2813,15) 30. What is the approximate hybridization state of the nitrogen atom in trimethylamine? A) sp B) Sp2 C) sp3 D) p3 E) dr"sp3 Short Answer: (10 Points) (3) Draw one complete Lewis Structure of CsHmO (2) (b) Identify the functional group(s) that you created in (a). (2) (c) What is the hybridization of the oxygen atom in (a)? (2) (d) Draw a resonance structure of your compound. (2) (e) What is the VSEPR shape of the carbon atom connected to oxygen? (2) Page 7 Answer Key WFQWPWP? p—an—np—t P??? H.— hm ,_. U5 h—II—i OOH-J ,_. >0 WthNMNNNNNN v—‘ PPWFQWPPPFP a oouwuw»>wacomnwm>wmoo>wm>mmwn Page 8 ...
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This note was uploaded on 04/17/2008 for the course CHEM 3411 taught by Professor Pohlman during the Spring '08 term at Saint Mary's University Texas.

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Exam 1-2006 - Test Form D Hour Exam One: ORGANIC CHEMISTRY...

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