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CH 4513-Spring 2024 Organic Chemistry | Exam 3 Chapters: 8-11 Version A ile wil) Lo 7 7 H He 100798 aoo26m2 oma EZ 3 7 Ta ] 3 | 10 Li | Be Bi] cyN F | Ne 65a_| sore oat | 20707 | r0067 | 159996 | risen] 201797 W 12 13 1S 16 7 18 Na | Mg Si Cl} Ar 2ases770| 24.3650 26581838] 2ooass pos737s1| sz0%6 | 354507 | 39548 w | 2 | 2 | 2 | 23 | 24 |] 2 | 26 [| 2 | 28 | 29 | 30 | 31 | 32 | 33 | 34 | 35 | 36 K_| Ca | Sc | Ti | V_| Cr | Mn]| Fe | Co| Ni | Cu } Zn | Ga | Ge | As | Se | Br | Kr aeons | aoare |2435s010]_a7ser | sosais | 19961 [sesaeoes| seas |sns3220c] sansze | oases | 6539 | 09223 | rze1_|raszieo| 7396_| 79506 | e320 37 | 3 | 3 | 4 | 1 | 2 | 3 | «| a | « | 7 | | 9 | so] st | s2 | 53 | 54 Rb | Sr | Y | Zr | Nb|Mo| Tc | Ru} Rh | Pd | Ag | Cd] In | Sn | Sb | Te | I | Xe ssacra | 0752 | easoses| s1224 [srsosse| see | 3) | 10107 |rorsosso} rasan fissséess| rian | rasta | 1i87i0 | 121760 | 12760 |r2e90007| 13129 = | | 7 | 2 | | ™ | 75 | 7 | 7 | 7 | 79 | 0 | o | o | 03 | 00 | 05 | 06 Cs | Ba | La | HE | Ta | W | Re | Os} Ii Pu} Au | Ui Tl | Pb | Bi | Po | Aty Ra rsasoses|13rse | recess | rans |reasers| asec | rssair | 19025 | rz2r7 | rosora|iaseess| 2008 | 2oussss| 2072 hoasoose| com | mia | a2 a7 | 28 | 69 | 104 | 105 | 105 | 107 | 108 | 109 | 0 | wm | 2 14 m6 718 Fr | Ra | Ac | Rf | Db} Sg | Bh | Hs | Mt 289) can | as | aan | aon | con | 2 | con | oss | 69 | cn | om | arm a7, 239) gon Bl] Ss)oO)a |e) ala |e ]«)a)e)e |] nH e | Pr | Nd} Pm | Sm] Eu | Gd | Tb | Dy} Ho} Er | Tm | Yb | Lu warns |reasores|_r4424 | ces) _| 15036 | rsisee | 15725 |isasrsee| 16230 frotozon2| 16726 fisssazi| r730s | 174957 oo | 1 | o | 93 | 94 | 95 | 96 | 97 | 98 | 99 Pa | U Np Pu | Am |.Cm | Bk | Cf | Es E 2320381 | avovsees] 2360289 ew | ver | om | an | as | asa 700 | 1 Fm | Md | No | Lr asn_| ass | aso | cs jor | 102 | 103, “As a Mississippi State University student, | will conduct myself with honor and intearity at all times. | will not lie, cheat, or steal, nor will accept the actions of those who do.” Print Name Student Signature Professor Date y) What is the major product for the following reaction? a. Hg(OAc)), HO b. NaBH, NaOH ° nl ie . DIE x ) oe + enantiomer B. OH ox 7 eae ) + enantiomer “WOH E. None of these choices. 2. What is the major product of the ere anh BO ees S fyms on mes reaction? * ALAN Odds 3. Which compound would have the lowest boiling point? O I att Ill myo B® <2HRO OQ Von Ora mf CH,OH IV Mow\t . Path Je cen ote ele. a4 Pies | Ae N4A~* on OH K What is the major product of the following reaction? yal ‘ =) A “4 0804; pyrdine Same, a cad HOWDY “eqns deeble bood ———_———_ > b.H,0, NalHSO, OH YY + enantiomer * HH 2 ep + enantiomer B. OH H fey 2 ra Cc p, CHsCO + (CH),CHCO,1 E. None of these choices, Mo 7. What is the major product for the following reaction? cre eo ae terbee O6G. Oh Me more.oe D. A. 8) C. wnat is the major product for the following reaction? yen Wey 8 or Gitg),S U5 wae \| a. 04, CH)Cly, -78 °C 2) Aurel debyd ug) b. Me,S a) 4 \debg = 0) hefure A. wren Yr asedes b tun Sans as hot ku no (Racemic) 7 2.) Cog 0. B. 3 \) whdekgto OC. a. + CO, ()) Weave. Cc. ’ Q, + HCHO e) More than one of these choices. 9. What is the correct IUPAC name for the following compound? OH 4 Ane & A. 4-isopropyl-3,4-dimethy|-2-bulanol B. 2,3,4-trimethyl-4-pentanol C. 1,1,2,3-tetramethyl-4-pentanol ®) 3,4,5-trimethyl-2-hexanol E. 3,4,5,5-tetramethyl-2-pentanol likely to be observed? AGS UY y a n cic Saari: 50m 8) . AQ 7 signals: all singlets 7 signals: 4 singlets, 3 doublets 3 signals: all singlets © 3 signals: one singlet, 2 doublets E. 3 signals: two singlets, one doublet consider the expected 'H NMR spectrum of 1,1,3,3-tetramethylcyclopentane. Which of the following is Huy oun AX right pexto cock A don COUNT AS hg ghbors 13. What is the structure of the compound in the following 'H-NMR spectrum with the molecular formula CcHiN? In the IR spectrum you notice a stretch at about 2250 om, Relative integration is shown, J cen } 7 | wy ge Yond , Ye “ ) 1s \Wil@ | triplet, 6H oy quintet, 4H quintet, 1H I r 4 2 ° : PPM = Sn en Jv a | Signals ee CN 2 YY Wg ovals CN eau an baal molecular formula 14, What is the structure of the compound in the following 'H-NMR spectrum with the CsiTi60? Relative integration is shown. pee _ ie oer doublet, 6H 5 triplet, 3H triplet, 2H quintet, 2H a: went S 7 : 3 ss 3 r ] : PPM 0 SN A C4 ° 4 00 OW \ey 7 Signe\s ny adele eee reload singhet ere Woe Noel ° const a 15. In NMR terminology, protons H, and Hy are said to be: D. Somer He cl a) a a %, vz > H H, 2 Ha 7 Ea bY A. Identical B. Enantiotopic @ Diastereotopic D. Homotopic E. Mesotopic -— in the following “H- with the molecular formula of the compound in the following 'H-NMR spectrum 204? The '3C-NMR snl i is lows peaks al 4 .8 ppm. Relative integration , CN spectrum sh eaks at 14.1, 40.8, 61.0 and 166.8 pp' is shown, -— singlet, 1H triplet, 3H quartet, 2H PPM 20. Which is the base peak? 100- 80 Intensity 6b- 40 -| 20- ns o@> 8 21. Which is the likely molecular ion (M*-)? o- 10 20 100- 80- > % 60- 5 £®- 20- Oy De 19 20 A. 15 B. 29 © 44 D. 45 E. 100 300 40 mz c& 30 40 miz 50 25. Which of the following is the most stable radical? wl yes. ag 3 Anis con be i eee both res- vuald we 2 3° alae é ally fic Yo BO 72 Wah D. @ 26. The reaction of 2-methylbutane with chlorine and light would yield how many monochloro derivatives? (include stereoisomers) AY ol, 4 tor ase ae Aw re Cl neal a cl cl S- yee ey (4) : aris 7) 27. Which of the following structures has the lowest bond dissociation energy of the bolded C-H bond? | 3 cH HY v v 2 o $3 allly\ie 2 3 4 5 6 @sorr H Hi I m Vv ° ° : (ee c AHighhe ung moe Sd 28, What would be the major product of the following reaction sequence? a 1, Bry, hv 2. CHjCH,OH, heat E, reveev ale "Se ei4 ~x? A a ee Ht it V y, I T AT B. I cm D.1V Ov 29. Which of these molecules is not expected to arise as a product of the high temperature chlorination of -y, methane? rN CCl U4 Ze (le u a A® HCC meals * AS CH2Ch ig i ie bt cla oeeeel D.CHsCHs= x 4 \ @) CHech L yawn f i y oye 8 30. A radical chain propagation reaction is one that: A. involves a series of steps. B. involves two steps of equal activation energy. C. is one that can be initiated by light. ® involves a series of steps, each of which generates a reactive intermediate that brings about the next step. E. involves free radicals that have an unusual stability and thereby cause a large quantum yield. 34, What would be the major product of the following reaction sequence? Ge inte Wotlb).Or Be es 1. HBr, ROOR, hv 2. t-BuOK, t-BuOH, heat OEt Ee hui OH 0) Tl i Iv v Ry ’t mean ay IV Lv A@o e5) 35. Carbocations are NOT intermediates in which one of the following reactions? Br A. po -upe —> AS OH Ve BON + 80, ——> pee © om + HBr ROOR,. Oe 0S0,H na + H)SO,———> z More than one of these choices. 4)e.a 0) WHE 2) 62 36. What is the major product of the following reaction sequence? 4 Eg Usa) NS \ bs 1. NaOFi, HORE, heat le Br) —3——____» 2a. KMnO,, NaOH, heat 2: hee 2b. H,0* (OH + enantiomer 10H xXx IH ny oy : aww aoc + C0; 
