HE2Key - CHEMISTRY 152.002 Spring 2005 HOUR EXAMINATIQE II...

Info icon This preview shows pages 1–7. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
Image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
Image of page 7
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: CHEMISTRY 152.002 Spring, 2005 March 10, 2005 HOUR EXAMINATIQE II ue i P ' r I 40 II 45 III 15 IV 10 V 15 VI 10 VII 15 TOTAL 150 Exam Begins Here I. (40 points). In the answer area below, darken the space of the most appropriate response to each of the following multiple choice questions. ANSWERS TO QUESTION I a b c d e a b c d e 1. H l H H H 5 H H I H H 2. I H H H H 6. H H H H a 3. H H H H l 7. H I H H H 4. H H H H I 8. H H H H 1 Initials k i; I 1. To which side would the following equilibrium lie? CI CI M0” + MC” —— M0 + W0“ Cl 0 0 Cl 0 O a. to the right. ® t0 the left. 0. neither, Keq z 1. d. need to know the pKa values of the individual acids before estimating. e. the equilibrium depends on the temperature of the measurement, and thus can’t be known. 2. Which of the following statements is E91 true of acetals‘? .Acetals are stable to acid. b. Acetals are stable to base. 0. Acetals are stable to reducing agents such as NaBH4. d. Acetals are stable to Grignard reagents. e. Acetals will not react with NaCN and pH = 10. 3. Which of the following carboxylic acids would NOT decarboxylate (lose 002) on warming? 0 o 0 $00” M0“ M0” 35 O o 0 H020 A B C D a. A b. B c. C d. D neither B nor D would decarboxylate on warming. 4. Which of the following would react slowest with MeMgBr (1 equivalent)? 0 o o o o doom, OAH dew dd drum/leg A B C D E Initials—KL 5. The reaction between and amide and water is slowest at which pH? a. 2 b. 5 ©7 d. 10 e. 12 6. Which of the following compounds would be the m acidic? +,H O + + + O’H O’H +,H 0’H l | | CI‘N | OCH3 H CH3 0/ NMee A B C D E 7. In the reaction of HCN at pH 10 of the following carbonyl compounds, the equilibrium would least favor the cyanohydrin product for which starting material? Um or (jam :clloi A B C D as» COWL‘D c. d. e. can’t tell without knowing the trend for the hydration reaction. 8. Which of the following statements about the Witti g reaction is/are n_0t true? a. The position of the double bond in unambiguous. b. All alkene substitution patterns (mono—, di-, tri-, tetra—) are readily available. (3. Only 2 alkenes are formed. d. a, b, and c. .bandc Initials k E: II. (45 points). Draw the structures of the major organic products of each of the following reactions. If no reaction would occur write NR Unless otherwise stated assume there IS enough of any reagent to do all possible reactions. Reaction mechanisms are not necessary. 0 1. (Di: Zn/Hg, EtOH m HCL24h o MegNH, PhH $5 2‘ pH ~ 4-5 0 o H 1. CH3CH2MgBr/ether 3 co 2- Vt \Q/LH PhCH: PPh _.._:_.3_._ 2- @135 @5 212222 0020113 #K“ /ut,_u._11 CH OH NH 5. g 3 2 2 + MjoH o warm 0020113 0 151 NaBH4/Et0H COzH1. 30012 7 i5 2. LiMezcu f3 R 0.41.13 'Arfo 7% (CH30H213N NR. CO2CH3 1. LiAIH [ether 4 U1 2 2 Ct“ 2— W21 NCH3 '--C_J-\ Initials k E I III. (15 points). Shown below are the structures of three acetals. In the corresponding box, draw the structures of the carbonyl and alcohol component pieces for each acetal. H300 OCH3 /Y<CH3 CH3 Q 0 O 0*): H30 I::> H CH? OCH20 3 IV. (10 points). When ester A was treated with excess ammonia the corresponding amide B was formed in high yield. On the other hand, when amide B was exposed to excess methanol under similar conditions the yield of ester A was very low. Explain this observation. Both reactions were conducted in sealed reaction vessels to prevent the loss of volatile materials. COZCH3 CONH2 NR3 -\— Um Ar— 1.650% “M is M Qfiuxlxbfiw S L MW 3 *\-\~L OS ilk—tum 0-9 panda. and lea ovexhgé m? 'o—L A. \A—ies sen/Q- v IA m a P> Aim/tides SJWAO swipe g stokewwms wittpméamimfi \ tLszx. & JL M J0“ note Méegp Cue. mnes‘a'io-Qfie. Mew/LL. (9:6qu e-g‘gifi‘i (5:; MQO‘COQ" C? [4.11:9 M iresWotMC-Q. {S {fibre Impom‘iw ts Oxyaxwxs. Initials E‘ E: V. (15 points). Show how you would carry out the following transformation using the indicated starting material and any other organic reagent containing two carbons or less. You may also use any inorganic reagents and solvents you might need. Show the structures of all intermediate compounds. Reaction mechanisms are not necessary. "PUMA HMCHQ —-——?——- HWCONHCHs 0 CH3 0 CH3 44/ fl L: \-\ Nam} “‘2. W5 0 Wm; u 3+ H ”33"” 6’ M5 Q“ m <-= m ’ we, CM} . MEL“; Ts? Initials k E 1 VI. (10 points). The following two alkenes were prepared by Wittig reactions. In the corresponding box Show one set of the carbonyl and ylid reaction pairs that would make each alkene. VII. (15 points). Draw a detailed reaction mechanism for the following reaction. Be sure to indicate the structure of the byproduct. lama—tn. O 3 1°” 63 miofiHSCHzMgBr (excess), ea ' OH £5? E x ether + byproduct 2. H30" H30 CH3 /&> 6&9 f 55"“3‘r {T Sgwagr E3 N33“ E 1/ ET 11;; ‘5 /\, Q =9 P 0 WEEK ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern