ORGANIC CHEMISTRY-2323; REVIEW 4; FALL 2010 1. The interaction of the x bond of an alkene with an electrophile can initially result in the formation of a species termed a x complex. Which of these cannot combine with an alkene to form a x complex? A) HY B) NE ©) Ag D) He E) BF: 2. Markovnikov addition of HI to 2-methyl-2-butene involves: A) initial attack by an iodide ion. B) initial attack by an iodine atom. ©) isomerization of 2-iodo-2-methylbutene. D) formation of a carbocation at C-2. E) formation of carbocation at C-3. 3. What is the major product for the following reaction? Page 14, What would be the major product of the following reaction? a aH db GS & 1 stg Tl Iv v AI B) Cc) Wl D) Iv E) V 5, Treating I-methylcyclohexene with HCI would yield primarily which of these? HC H3Ci HgC, oO oe) ne) I 0 m Hea aN Vv v AI B) I © ml D) IV 5B) Vv 6. How many compounds are possible from the addition of bromine to CHs-CHCH:CHs (counting stereoisomers separately)? A) One B) Two C) Three D) Four E) Five Page 27. (R)-3-Chloro-1-butene reacts with HICI by Markovnikov addition, and the products are separated by gas chromatography. How many total fractions would be obtained and how many would be optically active? ‘A) One optically active fraction only B) One optically active fraction and one optically inactive C)_ Two optically active fractions D) One optically active fraction and two optically inactive E) Two optically active fractions and one optically inactive 8. What is the major product for the following reaction? HBr — AX + enantiomer A) Br 8 B) ir + enantiomer c) eo D) ‘Br E) More than one of the above Page 39. What is the major product for the following reaction? ye HCI —> sS a) B) “wel oI E) mm 10. What is the major product for the following reaction? A) wk Br Uk yk + enantiomer Cc Br SK D) E) More than one of the above B) Page 411. What product would you expect from addition of deuterium chloride to 2-cyclohexyl-4- methyl-2-pentene? tio oF or I I att a aed oan cl Iv v Al B) Il QO m@ D) IV E) V 12. Addition of hydrogen chloride to the following molecule would produce: An Hh 2 G i cl a cl A~ AR AR AR ore a a ca a a 1 0 ™ IV v A) Landi B) Wand Il ©) TandIVv D) Vv E) All of the above are equally likely to be formed Page 513, What are possible products for the following reaction? “OD HBr —> Br a) “OS + enantiomer B) Br © O D) A)andC) E) None of the above 14, What is the major product of the following reaction sequence? —_—___- 2. NaCN, OMSO cl N CN + enantiomer CN + enantiomer yy RS > Ann Ann D) AW E) None of the above Page 615. 16. ‘What is the major product of the following reaction sequence? q 1. -BuOK, tBuOH ——_—_—_——_—— ah 2. HBr Br 5 ~>N Br hk B) 1 1 D,/Pd 1-Methylcyclohexene. —2—» mm 2-Methyl-2-heptene ae trans-2-Hexene HBL, Iv v AI B) I © m D) IV ER) Vv Page 1633. What is the major product for the following reaction? Ch Bry, CCly a A) Br \iBr + enantiomer B) Br bl + enantiomer Br oO B D) Br E) More than one of the above Page 1734, What is the major product for the following reaction? xs Ch, CCl, | YY 4) x . Soe B) a el + enantiomer Q oc xe + enantiomer D) E) More than one of the above 35. Reaction of trans-2-hexene with a solution of Br2in CCl, produces: 4 Br q Be} Hu Bu} er H fH 4 Br Br WW u « f Iv Vv A) Landi B) IandV C) MandIV D) IVandV ER) Vv Page 1836. The reaction of Bro/CCls to cyclohexene would produce the compound(s) represented by structure(s): H H H LE LEP aA Br Br Br 4 4 Br I 0 site A) Lalone B) Ilalone Cc) Mand I D) IMlalone E) I, Mandi 37. What would be the major product of the following reaction? oO Bry, HO 2 Qe Ow Ques Ow Ques OH be er "Br "OH I 0 MI Iv v AI B) 0 o m D) IV BE) Vv Page 1938. What is the major product for the following reaction? Bro, HO a + enantiomer A) + enantiomer Page 2039. 40. What is the major product for the following reaction? ~ Br, CH;0H eee sOH + enantiomer A) Br OcH, + enantiomer B) 8 Br + enantiomer © #0" OCs + enantiomer D) Br E) More than one of the above ‘What is the major product of the following reaction sequence? 1. Bra, HzO eS 2. NaH, THF A) 'OH B) ‘Br °) a Che oo D) E) None of the above Page 214. 42. What is the major product for the following reaction? 1,CH, — ZmCu) oe » Ov » E) More than one of the above ‘What product would result from the following reaction? KMnO,, 10, cold, dilute Choon ‘0 K "MnO, HOH 1 1 Mm OH OH Hou IV v Al B) I co m D) IV ER) v Page 2243. Hydroxylation of cis-2-pentene with cold alkaline KMnOy yields CHs CH CHs CHs re eo CHS CoHs CaHs CaHs I tl m Iv A) Equal amounts of I and Il B) Equal amounts of Il and Ill C) Equal amounts of Ill and IV D) [and Il as major products, III and IV as minor products E) All of the above in equal amounts 44, What is the final product of the following synthesis? H. i, OsO, 2-Bi —2__» St Final Pr hutyne NiB@s) Cts GLNalSo, Pine! Product CHy CH, CHy CH, “ee ~ ~ sc H7=S9H HOW = 4H H7~= You HOWE 4H Cis CH CH Hy I u ml v AI B) om D) IV E) Anequimolar mixture of III and IV Page 23,45. Which reaction would yield a meso compound? ; Br/CCly A) cis-2-Butene = —2— Hy/Pd anh 1) 050, DO, ii) NaHSO, trans-2-Butene SI KMNOs D) $C E) None of these 46. Which reaction is regioselective? a paw HL 0 Ol Ox" OH mM AR _KMn0y Ayr OH H va ee oee H AI B) I © m D) IV E) None of these Page 2447. Ozonolysis of compound Z yields the products shown below. What is the structure of Z? ° a) i it DO. 2HCH + CH3CCH,CH 2) Zn, HOAc O° 1 IL Il ° Ann vf Vv v AI B) Ul co m D) Iv BE) Vv 48. An alkene adds hydrogen in the presence of a catalyst to give 3,4-dimethylhexane. Ozonolysis of the alkene followed by treatment with zinc and acetic acid gives a single organic product. The structure of the alkene is: i CHCH=C-CHCH;CH, (is or trans) A) CH, fm CHyCH,C=CCH; (cis or trans) B) ‘HCH ge CHy-CCHCHCH,CH, © CHs ee CHsCH,CCHCH,CH, D) CH; ia (CHCH,CHCHCH=CH, B) CHy Page 2549. Addition of 2 mol of HCI to 1-butyne would yield: A) CHsCH:CH2CHCh B) CHsCHzCChCH3 ©) CHsCH:CHCICH.CI D) CHsCH2CH=CHCI E) CHsCHCICHCICHs 50. As the term "peroxide" A) ROOR B) ROOH o 9 al used in Chapter 10, it can refer to which structure(s)? c)_RCOOCR D) Answers A) and B) only E) Answers A), B) and C) 51. Which of the following free radicals is the most stable? CHa A) CHsCHCH,CH, fie B) CHCHCH,CH,- ee ©) *CHACHCHCH, CH (CHjCHCHCH, D) CH CHCCH,CHs E) a 52. Hydrogen atom abstraction from which position would yield the most stable free radical intermediate during the reaction of bromine with 2,2,3-trimethylpentane? A) Cl B) C2 Qo D) C4 EB) cs Page 2653. 34, Mono-bromination of the following alkane, S ; (using Br2 with light) would be? Br Br. *O- AO x + Br Br’ I Il I Iv Vv AI B) I © m D) IV 5) V Mono-bromination of the following alkane, AL, (using Br: with light) would be? . AL . . Pee ee poe oe) 1 I i Iv Vv A) I B) I c) Wl D) IV RV Page 2755. Mono-bromination of the following alkane, : C (using Bro with light) would be? Br Br Br I 0 mt IV v Al B) ©) D) IV E) Vv 56. Which hydrogen would be abstracted first when mono-brominating with Brz and light? He He Hd. Ha ‘Hd’ He Hd yeA HD Hal le He He A) Ha B) Hb ©) He D) Hd B) He 57. Which hydrogen would be abstracted first when mono-brominating with Br2 and light? Hi He He He He Ha HB Hb Hd Ha A) Ha B) Hb ©) He D) Hd E) He Page 2858. What would be the major product of the following reaction sequence? 59. —_~ A) B) o) D) E) 1. Bry, hy 2. CHjCH,OH ey SE hy oy ‘What is the product for the following reaction sequence? 1. Bra, hv —_ 2.H,0 wo ye A) B) ©) D) 5) I 1 m1 Vv v Page 2960. What would be the major product of the following reaction sequence? 1. Br, hv —s 2. #BuOK, ¢-BuOH, heat OH OtBu HOO oO I at i Iv v AL B) I ©) I D) Vv ER) Vv 61. What would be the major product of the following reaction sequence? 1.Bry, hy —— 2.CH;ONa, CH3OH, heat oH OCH, TO 1 1 I Vv Vv A B) © m D) IV 5) V Page 3062. What would be the major product of the following reaction sequence? 1.Brz, hy oe 2. ELOH, EtONa, heat I m Iv v A) I B) I ©) D) Vv BE) Vv 63. The p-orbital of a methyl radical carbon, CHs:, contains how many electrons? A) B) 2 Os D) 4 E) 0 64. What would be the major product of the following reaction sequence? 1. HBr, ROR, hy ——_——_—_—> 2. NaN, DMSO Ns DMSO No T tl IV Vv A) B) ©) D) E) ee Page 3165. What would be the major product of the following reaction sequence? 1. /BuOK, 1-BuOH, heat a Cl 2. HBr, ROOR, hv Br Br Br Br Br x OF OF OY & I 0 m1 Vv v et B) ©) IL D) IV E) Vv 66. What would be the major product of the following reaction sequence? 1, HBr, ROOR, hv Co 2. CH3CO3H, CH;CO;Na Co OH (Ox6CHy, Co ao NaN 1 0 Mm Iv v Page 3267. Carbocations are NOT intermediates in which one of the following reactions? Br ee . B) De + HyS0, ——> An An OSO3H D) + H,SO,——> E) More than one of the above 68. What is the major product obtained from the following reaction sequence? HBr 1:BuOK i) BH, THF 7 peroxides A tBuon BS ; ‘Bu ii) H,0,, OH oH oH aed AN YY 7 7 si Tl Tere Iv v Al B) © ml D) E) Vv Page 3369. 70. ‘What is the major product obtained from the following reaction sequence? Bry, {-BuOK, HBr NaSH, tw” * Buon” © ~peroxiaed” © Dp heat ‘SH SH Oo™ Om Ty OF o I u m IV v A) B) © i D) IV BE) Vv What is the major product obtained from the following reaction sequence? Bry, E:ONa_, HBr NaCN, Cr Eon ” B “peroxides © oe heat % wo & oN Oo Se hy OF OK, I 18 site iE v Ay B) ©) D) Iv RV Page 34Answer Key 8 FrROCCU> > Ano eM Owe > MOOU>OOWO>OOOMU>PUMOWWOUD>UD Page 3545, 46. 47. 48. 49, 50. 51, 52, 53. 55. 56. 37. 58. 59, 60. 61. 62. 63. 65. 67. 68, 70. O>MAMOBr>>>O>PONDOPOOMMBBB>A Page 36