CHEM2OA3 Fall 2010 Midterm V1 ans

CHEM2OA3 Fall 2010 Midterm V1 ans - Fail 2010 Chg-m ZOAS...

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Unformatted text preview: Fail 2010 Chg-m ZOAS Mad-harml Venspnl - MULTIPLE CHOICE SECTION: Questions 1-10; 2 marks each. 1. _Which of the fofltjfiring compounds is (Ej—S—propyI-non-tLen-S—yn a}? H . Am . B) B .‘/ D) D E)E 2. Which of tbs following pairs Qf compounds are geometric. (31‘s,. trans, ME, Z} isomcrs? .E)v Continued on next page I 3. Which of the follou'ring are resouance structures of compound‘l? [,0 — o I \N+-" \N'L" H>N+ l - l / ,, __ Q,_ 0* / toe- \N -.—.H ..N+ , * v iii . x iv_,_, A) i only B) i and iii ' C) i and ii E) iii, iv and V 4. The most iinportaiit (most thennodynamically stable) resonance structure for compound 2'13: i A) 1 because it correctly predicts that nitrogen is an atom that will be attacked by a X nuclet)” e V 6?; because all atoms have a completed octet ii because it correctly predicts that nitrogen 18 an atom that will be attacked by u‘ a nucleophile - D)‘ 1i because it correctly predicts that carbon 18 an atom that will be attacked by a 9t nucleophile E) these are two different compounds _ (X I /i[\ A a + Compouhd 2 Continued on next page Questions 5—6 relate to ethynylestradiol (compound 3). an anfit‘ertiiity hormone (used for I birth control; that also affects zebrafish). fOH .Compomd 3 5. What functional group is marked g in compound 3‘? (A) ketone (B) phenol (C) primary- alcohol secondary alcohol @tertiary alcohollm/ 6. ' Which of the following statements are TRUE? i) , He and l-ld have a mic relationship 9‘- ii) The double bond b has an E geometry ‘- iii) The relationship between 015g and alkyne h is trans K iv) The relationship between CH3: and {)I-ig is as \f . (A) ionly' (B) i,ii,iii (C) iii and iv (E) none are true 7. The following sentence has the fonnat “Statement 1 ‘B AUSE Statement 2”. Decide whether statement 1 is true, whether statement 2 is true, and whether the REASOWG (the ‘liecause’ relationship) hetWeen them is taint. Statement 1: 7 “l -butanol has a higher boiling point than ethanol” BECAUSE ' Statement 2: . “alcohol molecules are heir} together by hydrogen bonds”. Statement 1 and Statement 2 are both correct, and the reasoning is valid. :4. Statement 1 and Statement 2 are both correct, but the reasoning is NOT valid. Statement 1 is correct, but Statement 2 is NOT correct. a; Statement 1 is NOT correct, but Statement 2 is correct. a Statement 1. anti Statement 2 are both NOT correct at Continued on next page II Grade. ' 6 (My; flattij 8. Which of the following equilibria have 3 Km; e: I? i) O E?) “Kim - ./ :11) A0,“ + “xii“ —-.-—-—-——"'——m"" AD,“ . + \T/ K 0 . t; . 0 0 / iii) ”‘67 “ A» ____ AM + A- e V. A)i,0111y, B)iand ii C) ii only @ E) iii only 9. Which of the following best describes the dipole in a carbosylate anion (RC02‘)? ' ‘ Ft - R-i—Wib R ‘ (A) O\ (B) >20 (0) «0 (E) no dipole O_ o“ 0“ 10. _ Which of the statements is (are) true about the following equilibrium? COOH COOH H ‘1‘ tie + , + I “'5 H IN‘H m H a. H COOH coo" i) The addition of extra NH; will shift the equilibrium to the left K ii) The pKa of I-LiN” is smaller than the pKa of M63HN+ v’ iii) Km > 1 for the equilibrium shown / iv) The likelihood of deprotonating (removing H‘] from BOTH carboxylic acids increases as the Concentration of NHg increases. f A) all are true B) iand ii only-V 7C) ii, iii, and iv filD) iii and iv E) iv only Continued on next page WRITTEN SECTION: ill‘he following questions tequila written answers. 1. [4] This compound flissolves in pH 12 water much more easily than in pH 2. Suggest a reason why. Yeti may choose to complete the structurefs) below to illustrate yam-point, Reasonzfi'taé éaagoxtgmc‘ 1am: a; {EgfieaTuua—TI‘Efi A”? - . m» .5, :1 lMiZfi-t é‘r“: {3‘13 ts; 'he—E- tillagmlge‘), “H: ”:3“; TEAM AEG— Wafié} SOLvfiLE ml MATSQ ”fies . NEQZ‘RA L. (:4; Maoqojo 2. ' [6] Dtaw 2 additioiial resonance structures for each of the following molecules in - the boxes provided. Circle the more important (most thermodynamically stable) structure for each of the molecules FROM the stmcmre-s you drew. _ Continued on next page _ 3. [4] This is the infrar'cd spectrum of which of the following compounds (circle your mmwer)? m _ arm mm ”mm mm mm: sun 0 0*” - Briefly (1 —2 bullets) cxpléifi your reasopjng: _ CHKQONWL @ {#50 mm" W? mmfle gay-wag» XiEWQnJE- M, c%9}“L“fl‘c‘§ gm" No ‘03:: STRETCH mam; Continucd on ncxt page 4 [6] There are three parts to this question i) CIRCLE the moSt electrophjlic atom (most positively polarized) 1n molecule Q. H30 ,l—le Meo— 01 o _. Q Hi) ii) Which H will be preferentially removed by the base methoxide, circle the answer: Hag HI) or ® ? Draw the structure of the product below: TEE om] Ammo ls; Motle— sT‘qug "TEECIEEEEMQNS QEWEfl/E-EC-D ISL) Lafifi :29: 322%,. su- 3E3 lass—moss GEWAE-«E‘ is MOKé Eg‘ia? gflfijgéfl :‘EI’IE: "Ta‘qf'fi‘t‘ié {#EESQI‘Q t: Continued on next page 10 5'. {1:9} “16.16 are 3 parts [.6 LhiS unSfiGfl. Dapgfiuiug" uu we Launctlfl'fli' to ampefatlfi'fi, either reaction pathwayr (3— —butyn—2— one n), A or 3—butyn—2— one —-+ B ——> C) pathway could be followed— both reaction pathways are viable. - In the experiment done when methyl lithium was added to 3Jsut3m—24ene, and the reaction was stopped by adding water (quenched), a pure product was isolated using silica column chromatography The infrared spectrum of the product IS shown below. 0 1 9 UN MeLi 1 equiv MeLi R \q / 3—bUlyn—2—one \ Li “0 /J[\\ l EXCESS water ITFRARED Spectrum of the product: ..._........__H ...t._—-.-....-—...r«-4m Continued on next page 11 Question 5 cont. A) Does the infrared spectrum confirm that the. product is product A @l N ? B) Describc how yoil chose ycur answer to part A (2 bullets). -I LARQE (3H S?ce:cm C5: 2:300 CM ._,1 Amflq NE @- "‘ gmo cm C) In the reaction leading to A, did MeLi act as a base or nucleophile- (circle the anSWCI') /"— Basc uclcophile D) Draw the structures of product B and C (a reaction took place to give B and a second reaction attuned to give C) in thc boxes 0:: the reaction scheme. E) Which is more baéi‘c, an alkoxide Gran alkynyi anion (circle the answcr) V 0 If,»"“\ R" 4/7 Confinuicd on next page ...
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