CHEMISTRY.237.DARUWALA.FALL.2003.MIDTERM1

CHEMISTRY.237.DARUWALA.FALL.2003.MIDTERM1 - Department of...

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Unformatted text preview: Department of Chemistry, UniVersity of Washingon,‘ F all Quarter 2003 Page I of 4 Chem 237 (Organic Cherhisny —I); Section U (Version 2) Instructor: K. P. Damwala First Exam: Monday, October 27, 2003 Name: Id. No.: FIRST EXAM Check the quiz section you belong to by placing an “X” mark in the blank on the left corresponding to it: - Section Assistant m 3.30 .m.4.20 .m. 3.30 31:04.20 .m uc 4.30 m 105.20 .m. 4.30 .m. to 5.20 .m. 7.30 .m. to 8.20 m - Tuesda s 3.30 .m. to 4.20 .m. m 4.30....0510... 5.30 .mwo .m. Kan-Am... 6.30 .m. to 7.20 .m. Kati Arthur U. 3.30 .mmm .m ‘ Wednesda s 3.30 .m. to 4.20 .m 4.30 .m. to 5.20 .m. GUG 410 Jeff Wellhausen 4.30 .m. to 5.20 .m. BAG 331 A Kati Anhur 7.30 .m. to 8.20 .m BAG 106 Kali Arthur Time Iiflfilfilfl Iifi HEW 0"; Depanment of Chemistry, University of Washington; Fat! Quarter 2003 Page 2 of 4 'k Chem 237 (Organic Chemistry —I): Section U (Version 2) Instructor: [C P. Damwala First Exam: Monday, October 27, 2003 I) (3 points each). Fill in the blanks provided on the left of each of the following questions, m . corresponding to the correct answer that best describes that question. Do NOT CIRCLE THE LETTER: i 1) For which one of the following structures does the central atom have a negative charge? .. ' H H ' A) 3 1'7: x. B) | I c) I? .3"? D) 1L E) ‘6 _. c a at - , - _ __ .E/Bxig. lei/,-\ H H/ H H \H l-l/ \H ' .. ' ' H [-l H 2) Th: number of atoms that are sp hybridized in the molecule a shown on the ri ghtare 2' K 5 AM 3“ A) o B) 1 ' ) D) 3 E) 4 gem-,- cg 3) The felts/est number of pi (7!) bonds are present in which one of the following compounds? _ =C— E : "l— _"-_ _ u— _- "u H = -.. A) “30 g H C N B) HZN gig—N CH, C) HJC-C:C-N_Cl11 D) rile—fi—fi_n~—cn, E) Hc=c—C___c N112 3 l 3 2 0'7’ 4) The value of the C—~C—C bond angle in acetone (structure shown on the right) will be H acetone (3 (P2 15 a]. HaC—CuCI-la I, d )0” 180“ B) 120° C) 109.5° yf 90° ,B)’ 60° C \ \ / 5) Which one amongst the following species is least liker to function as a Brensted-Lowry a_c:i_d? / C C / accl- 340 Q5 if; / \ / \ a. I n _ pmf'a..$ A) H3C—Q-H B) H2804 C) :NH3 D) H3091 _ E) H30: + 6) What is the relationship between the two structures 1-! and 1 w d shown 0 the 'ght? Th yare H an . A . glut/l“ 7; , - 1 ' A) structural isomers _B)/resonance forms @c same compound ’19) different compounds E) oils—trans isomers 7) Which one of the following compounds will display the highest solubilin in H3C-CH2—CHz-CHz-CH3? 5 Q” E n v / A) H3C-CH2—OH B) H,c-CH2—Q:'+Na c) inc-oar, D) (H3C)2Nl-l 5) (11393011 9 7. Z Z ,1 I \Q’ ‘ \ I 8) Which one of the following functional groups is not present tic. absent) ,N/Cfis Q, 6* \ . 1-1 in atrcgine whose structure is showu on the right? ' , c: r/‘ Atropine A) aldehyde B) aromatic ring )Zf alcohol 01 CHz-Qll l" r o ‘ Pflster ’Bv)’ amine ; a, ' \ )\ 9) What is the correct IUPAC name for the bicycloalkane M shown on the right? a '0 ’ \ k ‘2 lo KL’ ' . A) bicyclo[5.2.0]heptane B) bicyclo[5.1 .01heptane 3 <:[:l M C) bicyclo[3.2.l]heptane D) bicyclo[3.2.0]hcptane E) bicyclo[3. l .l]heptane ‘1. ‘ 1 10) Which <_$eof the following is a correct and tin; statement regarding the (Bronsted—Lowry) acid-base theory? A The stronger the acid, the smaller or less the extent it will dissociate The conjugate of a strong acid is a strong base . C) The equilibrium for an acid-base reaction is always towards the formation of the weaker acid-base pair ,8) The more strong an acid, the less negative will be its pK. value y Hydrogen can never be present in the molecular formula of a Brensted-lowry acid +2 -_¢= .I Inc!) '- \. Department of Chemistry, Universio) of Washington; Fall Quarter 2003 Page 3 of 4 I Chem 237 (Organic Chemistry —I); Section U (Version 2) Instructor: K. P. Damwala i First Exam: Monday, October 27, 2003 II) Answer each one of the following questions as requested: A) (5 points each). Give the correct IUPAC name for each one of the following compounds: b) I CsHs ; 1H t. ?~ g'gflimauaq I ’ J ' .2 9 o ?—-+e+ra moth ’Inonane 3*d4'me ~5' hm. octane B) (4 points each). Draw a correct structure for each one of the following compounds: 3) 4-sec-butyl-6-ethyl-3vmethyloctane b) trans-1-mcthy]-3-cyclopropylcyclohcxane C) i) (6 points). Draw all the correct resonance structures for the compound shown below on the left. ® .. o. L p - H3C_9'_fi:C—C:9‘; “acflo :2: __ g)... H-I-l. ii) (1 point). Clearly mint out the resonance form that will be the (least stable or) minor contributor to the resonance hybrid. D) i) (4 points each): Consider the two trisubstituted cyclohexanc rings _1g and L shown below. Draw their most stable onf rmation showin the correct cis-trans relationshi of its substituents: CH, “*5 ,0 Bacon 113cc}!z .\‘CH3 H I L CH, W CH 3L“ '2 CH 3 H 0 ii) (2 points). Which compound E or L has a more stable conformation? L- (Insert the letter corresponding to that conformation in the blank on the left). tutu E) (1 point per blank). Arrange the following compounds in the correct order of the property that is being requested by placing the appropriate numeral in the respective blank below each compound: Order of basicity or ability to firnction as a base. (1 = highest; 4 = lowest). HJC.CH2-6: Hac-CH2.1's-1H- H3C£H2-S :' HSC-CHZ-IC-JHZ- 7Z3 #9. (Kw 31/1 g +' ' —__ I c o— “ML 33.33% “3C” 9*‘09 CM" C w 61 uLCJ 4 “Gen Department of Chemistry, University of Washington: Fall Quarter 2003 Chem 237 ( Organic Chemistry —I),' Section U (Version 2) Instructor: K. P. Domain First Exam: Monday, October 27. 2003 Page 4 of 4 F) (3 points each). Drawonly one correct structure of a conqaound of molecular formula C5H11Cl that has 1) at least one methine carbon atom present in its slructur / 2) a quaternary carbon atom present in its structure G) (2 points each). In the blank provided to the lefl of each pair of species, place the letter corre compoundispecies that best displays the property that is being requested. 1 l/ 1) & anonpolar molecule 2) E ‘gvtlgstronger acid F3C-CH2—COOH 8%? higher oxidation state 4) £2 has a higher boiling point 5) CHZClz A_ 0R ccn g l ..--"' g OR :fi: 0 E C _ Hi '51.] 3-methylhexanc Q ‘l will consume greater moles of 02 (g) during complete combustion F3CrCH2-CH2—OH n : 0: II -| HC‘C‘ E 3 Cc,“ ‘1 JV? lo 00H“; 'i' O?’ "@601 git-£0 0R H or 2,4-dimethylpentane g _|, CGHIZ 1 0R CGHIO J I) H) (2 points each). Identify whether each of the following reactions is either an oxidation or a reduction or neither by H20 correctly filling in the blank wn on the lefi. N lift Ms“ _ + __ — Q 0H H 0 H 3‘ " 2) - :03 :0: ll PCC ll —-—.—-—’ _ V3 \H CHIC]; \/C \6H : J(1“ +3 ._ 3) fiduch 1'13ch EN: “M144 ! HsC-CHl-fiflz ‘ “’t '1; 0 (3 points each). Write the correct structure of the product for each of the following Lewis Acid-Base reactions. A_11 structures should be com lete with the re er number of atoms unshared electron at and an cha es: or” ii ML \NQ/cfii'cg 1) 1, . 3) Total Score: 5 3 I 100 points. ...
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This note was uploaded on 03/03/2010 for the course CHEM 237 taught by Professor Andersen during the Spring '08 term at University of Washington.

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CHEMISTRY.237.DARUWALA.FALL.2003.MIDTERM1 - Department of...

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