SampleExamIIAnswers - NAME flaw/“3”/g SSN FLORIDA...

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Unformatted text preview: NAME flaw/“3” /g SSN FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry Dr. Keller EXAM II CHM 22H - Fall 2001 Be clear and neat; a poorly—drawn structure may be misinterpreted. To obtain partial credit, you must show your work. I. NOMENCLATURE AND CONFORMATIONAL ANALYSIS 1. Provide a complete IUPAC name for THREE of the following compounds. Where appropriate. indicate the specific stereoisomer as part of the name. [5 points each] 2. There are 3 different staggered conformations of 2-butanol — looking down the C2-C3 bond. Draw these 3 conformations on the templates below. circle the least stable conformation, and explain briefly (1 sentence) why it is the least stable. [7 points] CHM 2210-01 Fall 2001 EXAM 11 Page 2 3. Using the template below, draw Irans-1-isopropyl-3-Inethylcyclohexane in its most stable chair conformation. [4 points] 0A7 ((39% 2. II. STEREOCHEMISTRY 1. Place an asterisk (’1‘) next to each stereocenter in the antibiotic Tetracycline: [5 points] Tetracycline 2. Using the template below, draw R—1,1,2-trichlorobntane: (For partial credit, you must show your work.) [4 points] CHM 2210-01 Fall 2001 EXAM II Page 3 3. Provide a brief (1-2 sentences) definition for THREE of the following terms: [3 points each] a. optically active: ‘1’“ OLE-(L5 7L° VTM PPQWVE I“? (“MM (Wat. b. confi oration: (rice g «2365' I ' c. conformation: W {A 0‘ Wag/69% LUKWM WM 67 mad-mg, armtl 6k rcgma bmath digexiifmdflwfimmj f/(A-Ld WI 01/4ch U" 174% dim}. _ safcw) N? a 4. Consider the compound HI— ' OH _ _.__‘ ( ) shown at the right: 6‘ k ’4’ c) 0 H-I- 0H ‘1' ) H'" *0 a. Determine the configuration of each stereocenter (show your work): [4 points] C“ K H '1' 49 (9 (4 # "Eye—f 0 3 (:40 1). Draw. a diastereomer of this molecule AND indicate whether or not it is optically active. [3 pOIHtS] gt“) M CHM 2210-01 Fall 2001 EXAM II Page 4 5. Using the following 3 structures, OH OH 0}] 191-1 - Cunt“ .1.“\Cl “N‘Cl Curl-l; O ul‘“Cl A B 'C D OH 0H 9H 9H '3- CU”... . C1 ClCl CMM.C1 C1 sulCl E F G H a. Which of the above stereoisomers are mesa compounds? [1/2 point each] 442s b. Which of the above pairs of stereoisomers are enantiomers’? [1/2 point each] GAE j C-M‘H c. Which of the above structures are identical compounds ( give your answers in pairs)? [1/2 point each] f C +// III. NUCLEOPHILIC SUBSTITUTION A. Draw the structure of the lettered compound in FOUR of the following reactions. Where appropriate, be sure to show the structure as its correct stereoisomer. [4 points each] C“) ' B!" e acetone _ 1. . ' ' + CN ————-——I- CHSOmMCN A . from only 2. +%W/_h @ +Bre \ CH3 IB CH: CHZCH2CH3 CHM 2210-01 Fall 2001 EXAM II Page 5 H . u Ht . CH low 06‘) - at? 3‘ “ izn + H20 ' + >4“ 3 . temperature Br I H— _ _ C D 4- O. wheeler—u + Br I E F 5. - CHZCHZ-O—Ef CH3 +1e O G B. Explain BRIEFLY what is m with the fellewing two reactions as written. What, if anything, will happen instead, and why? [3 points each] 1. Ax + +0615.) —:-- X0 + KCl 30/anch + 3WW M /\)< out“ 5am £lxwvm24l‘k @ OH NH3 6 2. 0‘ ———=~ . @551 Labor!” {CM/ma CHM 2210-01 Fall 2001 EXAM II Page 6 C. Shown below are two different ways to prepare the same ether by nucleophilic substitution: H3 H3 ‘f e e i 1- CH3"'(|3—0 K + CH3CH231’ ----—I- CH3—(IZ—OCH2CH3 + KBr CH3 CH3 (EH3 ' (ISH3 2. CH3CH20H + CHa—f—Br —* CH3-'(|:—ocnch3 + H3:- CH3 CH3 For each reaction predict: a. What happens to the rate of the reaction if the substrate concentration is doubled? [2 points] Reaction #1: M CPI Reaction #2: M Q; b. What happens to the rate of each reaction if the substrate concentration and the nucleophile concentration are doubled: [2 points] Reaction #1: M .. Reaction #2: D. Which of the following compounds is the poorest nucleophile (circle it)? [2 points] e - 0 E. Which 8N2 reaction will occur most rapidly? Circle the correct answer. [2 points] 1. CH3SH + CH3] ——--——-+ e CH38 + CH3I -- 3 . 30H + “'_+ e 4. 30 + CH3 I ————-i- 5. CH3Se + CH3C1 —-—--'—n- CHM 2210-01 Fall 2001 EXAM II Page 7 F. Eliminations are favored over nucleophilic substitution reactions: [2 points] a. at high temperatures. b. when t-butoxide ion is used. c. when 3“ alkyl halides are used as substrates. d. when nucleophiles are used that are strong bases and the susbstrate is 2". in all of these cases. G. Write an equation showing how you might synthesize THREE of the following compounds from an alkyl halide and a nucleophile. [4 points each] 51- <:><:: W; flaw ...
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This test prep was uploaded on 04/20/2008 for the course CHEM 2400 taught by Professor Kellerfiu during the Fall '09 term at Nova Southeastern University.

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SampleExamIIAnswers - NAME flaw/“3”/g SSN FLORIDA...

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