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ORGCHEM1FREVF10 - ORG CHEM—1 FINAL REVIEW FALL 2010 ESSAY...

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Unformatted text preview: ORG. CHEM—1; FINAL REVIEW, FALL 2010 ESSAY. Write your answer in the space provided or on a separate sheet of paper. 1) Draw a correct Lewis structure for chloromethane, CH3C1. 2) Draw a correct Lewis structure for boric acid, B(OH)3. 3) Draw a correct Lewis, structure for t—butanol, (CH3)3COH. 4) Draw a correct Lewis structure for acetonitrile, CH3CN. MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 5) Which of the following are correct Lewis structures, including formal charges, for nitric acid, HN03? . O C O 0 C O O O .I U. I. II I. .. ll .. H—N=O H—o~—N—o:- H—0~N=o H o o. + no 0' I. A) A only B) B only C) C only D) both B and C E) all of the above 6) Which of the following choices represent(s) a pair of resonance forms? A) :02 20H II I CH3CHZ— C‘H , CH3CH= CH 3) + I. + CH3CH—OCH3 , CH3CH=0CH3 C) H H \ .0 C=C=N - . -:Cfl: / ~' I H H D) bothAandC E) hothBandC ESSAY. Write your answer in the space provided or on a separate sheet of paper. 7) Consider the set of compounds, NH3, HF, and H20. Rank these compounds in order of increasing acidity and discuss your rationale. 8) Use the curved arrow formalism to indicate the movement of electron pairs in the following reaction. (CH3)3C_C1: + A1C13 "_—-> (CH3)3C* + A1C14- 9) Draw the other important resonance form of: + HZE-N-EN: 10) Draw the important resonance forms of: MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 11) Which of the following statements about n molecular orbitals is/are correct? 11) A) When two atoms are connected by a double bond, both of these bonds are nbonds. B) Most of the electron density in a n molecular orbital is centered above and below the internuclear axis. C) 7: molecular orbitals are cylindrically symmetric. D) Both statements B and C are correct. E) Statements A, B, and C are all correct. ESSAY. Write your answer in the space provided or on a separate sheet of paper. 12) Draw the important resonance forms for the structure shown below. dx/ MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 13) Choose the correct hybridization for the atom indicated in the molecule below. 13) CH; \ /c=c=c;"1111 m3 f A) sp2 B) sp3 C) sp D) none of the above 14) Choose the correct hybridization for the atom indicated in the molecule below. 14) O H C / \ CH3 T H A) sp B) sp3 C) sp2 D) none of the above 15) Choose the correct hybridization for the atom indicated in the molecule below. 15) CH, \ lc=c=c-,"}}II CH3 f A) sp3 B) sp2 C) sp D) none of the above ESSAY. Write your answer in the space provided or on a separate sheet of paper. 16) Provide an acceptable name for the alkane shown below. fawn; )2 CH3CH2CH2CH2CH2CH2CHCH2CH2CH3 17) Draw an acceptable structure for 6-ethyl—2,6,7—trimethyl-S—propyhionane. 18) Draw the most stable conformation of trans-1,2—dimethylcyclohexane. 19) Draw the most stable conformation of cis-1,2-dimethylcyclohexane. 20) Provide an acceptable name for the alkane shown below. 21) Give structures for the three isomers with molecular formula C5H12 and provide the common name of each. 22) Draw the important resonance forms for the structure shown below. 23) Draw an acceptable structure for 4-t—butyloctane. 24) Draw an acceptable structure for 1-ethyl—2-(2,2-dimethylpentyl)cyclopentane. 25) Draw an acceptable structure for 4-isopropyl—2—methylheptane. 26) Use the curved arrow formalism to show the movement of electron pairs in the following reaction. cnacuzoz +CH3—IZ ———-* CH30~CH3+ :12 27) From the perspective of viewing down the C2-C3 bond, draw the Newman projection of the least stable conformation of 2,3-dimethylbutane. 28) When light is shined on a mixture of chlorine and chloromethane, carbon tetrachloride is one of the components of the final reaction mixture. Propose a series of mechanistic steps which explain this observation. MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 29) Which of the following is not a possible termination step in the free radical chlorination of 29) methane? A) Clo + wall —> Cl—wall B) oCH3 + wall —’ CI-13—wall C) oCH3 + C12 —-> CH3C1 + C1- D) -CH3 + C1- —> CH3C1 E) .cr13 + cm -> CH3CH3 ESSAY. Write your answer in the space provided or on a separate sheet of paper. 30) Write a detailed, stepwise mechanism for the following reaction. A Q—cns + (:12 ——> Q—cnzcn HCl 31) Label each assymetric carbon in the compound below as R or S. SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 32) If possible, draw the structure of any diastereomer of the molecule shown below. 32) Elr CH3 H30 CH3 ESSAY. Write your answer in the space provided or on a separate sheet of paper. 33) Label each asymmetric carbon in the compound below as R or S. CHa 34) Provide a detailed, stepwise mechanism for the reaction below. (CH3)2CHCH2CH2CH21 + CN- —> (CH3)2CHCH2CH2CH2CH2CN + I- 35) Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation. I CH3OH __.._’ H" CH CH A 2 3 36) Label each asymmetric carbon in the compound below as R or S. $02“ ..-C CHJ‘i: \ H 37) When 1-bromo—2, 2-dimethylcyclopentane is heated in ethanol, one of the products which results is shown below. Provide a detailed, stepwise mechanism for the production of this compound, and give the name of the mechanism by which it is produced. Q/ CH3 CH3 MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 38) Which of the following alkyl chlorides will undergo 3N2 reaction most readily? 38) A) 3-chloro-2-methylpentane B) 2—chloro—4—methylpentane C) 2—chloro—2—methylpentane D) 2-chloro—3-methy1pentane E) 1—chloro—4—methylpentane 39) Which of the following solvents could be described as polar and protic? 39) A) acetone B) acetonitrile C) ethanol D) dimethylformamide E) 18-crown—6 ESSAY. Write your answer in the space provided or on a separate sheet of paper. 40) Provide the proper IUPAC name for the alkene shown below. CICHZCHK CH3 / C=C / \ H H 41) Draw all likely alkene products in the following reaction and circle the product you expect to predominate. Br NaOH ”0.13 —————> mom MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 42) Which of the following compounds is the most nucleophilic? 42) A) CH3OH B) BF3 C) H20 D) CH3C02H E) CH3SH ESSAY. Write your answer in the space provided or on a separate sheet of paper. 43) Draw all likely alkene products in the following reaction and circle the product you expect to predominate. 44) Propose a detailed, step-by—step mechanism for the reaction pathway shown below. CH3 H2804 ’ CH3 —‘——‘"hw OH . CH3 45) Draw all likely products of the following reaction and circle the product you expect to predominate. H2504 CH3CH(OH)CH2CH2CH3 ——> 46) Draw the alkene product which results when 1-bromopentane is heated in acetone containing NaOH. Give a detailed, step—by-step mechanism for the production of this compound. 47) List the following radicals in order of increasing stability (i.e., from least stable to most stable). (CHa)3C-. CH2=CHCH2-, CHaCH2-, CHs-, (CH3)2CH. 48) Complete the following reaction and provide a detailed, step-by—step mechanism for the process. CH 3 BIZ _—.—.. 49) Complete the following reaction and provide a detailed, step—by—step mechanism for the process. >=F—“L> SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 50) Rank the following dienes in order of increasing stability: trans—1,3-pentadiene, 50) cis—1,3-pentadiene, 1,4-pentad1'ene, and 1,2-pentadiene. MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 51) What descriptive term is applied to the type of diene represented by 2,4hexadiene? 51) A) cumulated diene B) alkynyl diene C) conjugated diene D) isolated diene E) none of the above 52) What descriptive term is applied to the type of diene represented by 1,5—octadiene? 52) A) isolated diene B) alkynyl diene C) cumulated diene D) conjugated diene E) none of the above ESSAY. Write your answer in the space provided or on a separate sheet of paper. 53) Draw the major organic product generated in the reaction below. Pay particular attention to regio— and stereochemical detail. / 1. H10»), H10 2. Nan. ' 54) Provide a detailed, step-by-step mechanism for the reaction shown below. / arm... Q=< ____—_—.. H0 55) Provide a detailed, stepwise mechanism for the reaction shown below. (I «a CE 0“... A I OCH3 SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 56) Provide the structure of the major organic product in the following reaction. 56) 0 CH3 ., A. \< O ESSAY. Write your answer in the space provided or on a separate sheet of paper. 57) Provide the structure of the major organic product in the following reaction. C02CH3 Q + f —" 58) Provide the structure of the major organic product in the following reaction. 0 0 CH3 / A + CH3 —"'—+ \ 59) What are the structures of A, B, and C? NBS A NaOCH;CH_q, B CHO CH2=CHC01H C l- 0: _____—_. ————. 2. S(CH3)2 H020 CHO 60) Provide a detailed, stepwise mechanism for the reaction of benzene with Br2 and FeBr3. Make sure to include the activating reaction between B12 and FeBr3 in your mechanism. 61) When 1—methylcyclohex-2-en-1-ol is treated with HBr, two constitutionally isomeric bromides are produced. Provide a detailed, stepwise mechanism which explains this observation. 62) Provide the major resonance structures of the ion which results when the most acidic hydrogen of cyclopentadiene is lost. MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 63) In electrophilic aromatic substitution reactions the hydroxyl group is an o,p-director because: 63) A) it donates electron density to the ring by induction and stabilizes the ortho, para sigma complex. B) it donates electron density to the ring by resonance and stabilizes the ortho, para sigma complex. C) it withdraws electron density from the ring by induction and destabilizes the meta sigma complex. _ D) it donates electron density to the ring by resonance and destabilizes the meta sigma complex. E) it donates electron density to the ring by induction and destabilizes the meta sigma complex. 64) In electrophilic aromatic substitution reactions the nitro group is: 64) A) an o,p—director since it stabilizes the ortho, para sigma complex less than the meta. B) a m—director since it destabilizes the meta sigma complex less than the ortho, para. C) an o,p-director since it stabilizes the ortho, para sigma complex more than the meta. D) a m—director since it destabilizes the meta sigma complex more than the ortho, para. E) none of the above. 65) The nitration of anisole: ' 65) A) proceeds more rapidly than the nitration of benzene and yields predominantly the ortho, para products. B) proceeds more slowly than the nitration of benzene and yields predominantly the meta product. C) proceeds more rapidly than the nitration of benzene and yields predominantly the meta product. D) proceeds more slowly than the nitration of benzene and yields predominantly the ortho, para products. E) proceeds at the same rate as the nitration of benzene and yields predominantly the meta product. SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 66) Draw the four major resonance structures of the sigma complex intermediate in the 66) reaction of anisole with HNO3/H2504 to yield p-nitroanisole. ESSAY. Write your answer in the space provided or on a separate sheet of paper. 67) Draw the three major resonance structures of the sigma complex intermediate in the reaction of acetophenone with HNO3/HZSO4 to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two. 68) Provide a detailed, stepwise mechanism for the following reactions. (CH3)2CHCH301 —! AlCl3 69) Provide a detailed, stepwise mechanism for the following reaction. C(Cfis)3 F -0CH3 N02 N02 70) Provide a detailed, stepwise mechanism for the following reaction. _ NH, + NaNHz—p Q + NaBr 71) Draw the four major resonance structures of the intermediate which results when o—nitrochlorobenzene is treated with NaOH. Br 10 72) Complete the following reacfion and provide a detailed, step-by—step mechanism for the process. H+, 11,0 11 Answer Key Testname: ORG. CHEW—2323; REVIEW 4A; SUMMER 2009 1) H H H—F—CIZ or HiCZClZ H H 2) n \. 50° 3—3—11 H :0. . :o: I. I......... H or 11.9.3.9.11 3) ‘u‘ H—c—H H l .- H——(|:-—C—o-H H | H—CI-H H 4) ’I‘ H—(lz—CEVZ H 5)B 6)E 7)NH3<H20<HF When determining relative acidity, it is often useful to look at the relau've basicity of the conjugate bases. The stronger the acid, the weaker (more stable, less reactive) the conjugate base. In this case, one would look at the relative basicity of F-, OH-, and NH2-. The relative strengths of these species can be gauged based on the electronegativity of the charged atom in each. Since fluorine is the most electronegative, F- is the most stable, least reactive base in the group. This means that its conjugate acid, HF, is the strongest. (CH,)3C -—® 3) m, ——-—»- (CI-1350* + MCI: 9) + -. H2C=N=N.‘ 12 Answer Key Testname: ORG. CHEM-2323; REVIEW 4A; FALL 10 1) lil H H-IC-ClI or H2CIC12 H H 2) 11 \. 50' 3—3—3 H :0. ' :o: I. C....-.... H or HOROB...IH 3) ‘i H—C—H H I .- H—c—C—o—H n I H—Cl—H H 4) ‘1‘ H—c-CENZ H 5)B 6)E 7)NH3<H20<HF When determining relative acidity, it is often useful to look at the relative basicity of the conjugate bases. The stronger the acid, the weaker (more stable, less reactive) the conjugate base. In this case, one would look at the relative basicity of F-, OH-, and NH2-. The relative strengths of these species can be gauged based on the electronegativity of the charged atom in each. Since fluorine is the most electronegative, F- is the most stable, least reactive base in the group. This means that its conjugate acid, HP, is the strongest. 3) ((13,); —® m3 ——> ((11350 + MCI: 9) + -_ H2C=N=N.' 12 Answer Key Testname: ORG. CHEMI-2323; REVIEW 4A; FALL 10 10) CPI: .‘_ C113 C113 _ U 9 U 9. U 11) B 12) ONHOT" 13) C 14) C 15)B 16) 4—isopropyldecane g 4-(1—methylethyl)decane 17) CH.)- CH’ CH: CHa CH: Cl-Ig CH; 18) W CH: 19) flCHg 20) 5-sec-butyl-2,2-dimethy1nonane g 2,2-dimethyl—S—(1—methylpropyl)nonane 21) AAA/7L pentane or n-pmtane isopentane neopentane 22) :b' :0: CH3 QCHJk 13 Answer Key Testname: ORG. CHEM-2323; REVIEW 4A; FALL 10 24) a CH! CHa CH: 25) . ([33 CH3 OCH; (1%; CH; CH3 CH(C33 )2 26) Me 28) CH3C1 + C1- —> ~ CH2C1 + HCl ~CH2C1 + Cl-Cl —» CH2C12 + Cl- CHzClz + C1. —> .CHClz + HCl ~CHC12 + Cl—Cl —> CHC13 + Cl- CHC13 + C1- —> -CC]3 + HCl ~CC13 + 0-0 —> CC14 + Cl- 29) C 30) (mg. Cl—C1—. 201° 0.0“” + H—CH2 Ph—’ - CH2Ph + HCl propagation (resonance stabilized) steps 0 ml PhCHz- + c1— 1 —> PhCH2 Cl + Cl- 31) elk S 14 Answer Key Tesmame: ORG. CHEMI-2323; REVIEW 4A; FALL 10 32) w -I H I||Hllltm I u 0; O I m o H I on 0; EH3 CH3 33) W3 _' 0H 9CH3 34) A (033) CHCH2CH2CH2T} + CN'—->(Cfls)2CHC32CHch2—CN+ 1' 1- ~ 0 I"I 'I CH20H3 "CH2CH3 1- 02H rearrangement —————> "' 014120113 CHchs CH20Hs am :4 CH2CHs 36) sq?” CH, w" F’C H 35) 15 0 I u Answer Key Testname: ORG. CHEMI-2323; REVIEW 4A; FALL 10 E1 mechanism 38) E 39) C 40) (Z)-5—chloropent—2-ene 41) 0/ + 42) E 43) Answer Key Testname: ORG. CHEMI-2323; REVIEW 4A; FALL 10 M+.+K/\ d H H W +-0H—P/\/\+H10+Br‘ 47) CH3- < CHaCHz- < (CH3)2CH. < (CH3)3Cc < CH2=CHCH2. BI" CH3 Br CH’ 0 - ., '0 @Br Br H “331‘ + —p> "3'13 48) V "Br 49) Wfi-F +Bf——r- B! 50) 1,2-pentadiene < 1,4—pentadiene < cis-1,3-pentadiene < trans-1,3-pentadjene 51) C 52) A 53) 45) 46) 0H Mfr 0 WW 11% 17 Answer Key Testname: ORG. CHEW-2323; REVIEW 4A; FALL 10 55) H + OCH3 m + CH39H —> etc, 56) H 0 CH3 H o 57) H C02CI'13 58) CH3O Urms O 59) Br A G B G C H Answer Key Testname: ORG. CHEMI—2323; REVIEW 4A; FALL 10 60) + - Br—Br:/+\~FeBr3 —- Br—Br— FeBr3 -—— Br '5' _ _ OflBr-Kgr— FeBrs —D OH 4- F834 4. Br Br + CH3 61) 19 Answer Key ‘ Testname: ORG. CHEM-2323; REVIEW 4A; FALL 10 00113 OCH3 ocns ocns H + H N02 H N02 H N02 0 CH3 0 CH3 0 CH3 H H H 02 H N02 H N0; + + ) (\ + _ (CH3)2CHCH2—Cl + A1013 H(CH3)2CHCH2* “(:14 (1113 CH3 + I 033 -cl:- —> CH2. -c -CH3 + H 69) F F 7 OCH3 OCH3 N 02 N02 N02 20 Answer Key Testname: ORG. CHEMI—2323; REVIEW 4A; FALL 10 + RH; . + NH3 + Bf (\ NH: \/2 _ G + NH2 —> NE: NH, 71) _ Cl (:1 Cl Cl H H _ _ - + 0 N02 N0; N0 \N" o' 21 ...
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