Instructor: Manoharan Mariappan, Ph.D., Dept of Nat. Sci., NFC, Madison, FL HOME WORK — Il (CHAPTER-3), 15 points +5 bonus points to TEST-1 ORGANIC CHEMISTRY —1_ (CHM 2210), FALL 2020 Name & IDE (GAR Fallec Due date: Fri, Oct. 3, 2020 1) Show which pair of structures are identical, constitutional, resonance and non-identical. i CAs erence Ay yd Beseoane ALL Watton , sondiassi : jumber the longest carbon chain to match the IUPAC name of each alkane below. 2) See ot aisobuy-2-metyoctane or aes Atortbuyt2.7-dimettyiociane 4-etmy.2.5.6.8etametiyi7-propyidecane 4-0thy'3.6.7-timetryknonane 3) Apply IUPAC rules and provide a systematic name for each of the following alkanes, cycloalkanes and bicycloalkanes. Numbering the chain or cycle is needed for each compound, 2 : te 3-elnut oe methyl hexane 2- clove ~ 3,5, U-benme Huylheptane 4 thors -3-e8 ¥ —trwwecveyl- seoorednglocteanieInstructor: Manoharan Mariappan, Ph.D., Dept of Nat. Sci., NFC, Madison, FL C+(3 ae an ae ess " 2. 4 e (Coy CHG nerseH(CHCTE)CHLCICHy)s . oe NG ,2,E—teimetiyl ockane ne tN a aa HyCCHCH,CCH,CHCH, CH, - i CH O(CHad 2,2)5\3- Fe camne thy) 6 F -OMMO= 3 -ethyl 2255 + eecea tetramethylodte Ne .\ B-ery! COR CH crypt Choe oH 1 -{soeeney) — L=mnesnuloctene Bereta) —B, 4 dronetnyloctcige WN 3,4 tA Slurs wane Example: ChCH-CH;-CHaCI 1,1,3-trichloro propane. Drawing Instructions: Draw skeletal strictures corresponding to each of the given names. Draw: 6-ethyl-4-isopropyldecane . oeInstructor: Manoharan Mariappan, Ph.D., Dept of Nat. Sci., NFC, Madison, FL BC 3c 4) (I) Use Newman projection to Illustrate “four possible conformations of 2,3-dibromo-butane. Eully Eclipsed Gauche hs sd ally 7 H Lo3 eg wv 9 OC War ec —aiaseae 2 - agg ae i we lle Ay ‘ Gauche Ectipsed | Fully Eetipsed She Z ‘Decrease in the stability order Xe at i wf Paks 7 Couche Zfstiose 7 lly ec tigseed — ite (1) For2,3-dimethylbutane, draw the most stable “anti” form first and then accomplish both “gauche” and “eclipsed” forms by using appropriate rotational (torsion) angle.Instructor: Manoharan Mariappan, Ph.D., Dept of Nat. Sci., NFC, Madison, FL {lil) Obtain other conformations by clock-wise and counter clock-wise rotation for the following two compounds (3,4-dimethylhexane and 2,3-dichlorobutane). rv 4 8 300° W Ht A oe, 4 Belipsed - = Woy ey Hot 207 ots ize | 1 eh « ens H CH 4 cng Gauche A Jj 20 OM ul Uh, y u 4 Hs t aInstructor: Manoharan Mariappan, Ph.D., Dept of Nat. Sci., NFC, Madison, FL 1) Draw Constitutional isomers of a cycloalkane with the M.F. CcH:2 and also name each of the isomer. Osgh = yelotoulane \ya-dometh, I-enet r 'o v eo Aa L.Z-d Cytiohexane Ni ley leReokne, Ayhcdsivet a) ble Bulo eT nome Hyelolodude b Vokes swety J 2,3 —Heyedhyleyelpragon cg Latnoroea’ ne H SICHs)s a et nycrn iH ‘5 OI ll lala 3) Draw cis-1-sec-butyl-2-ethyleyclopentane S's Gem Lael 4) Draw 3,5-dieyclohexylnonane iInstructor: Manoharan Mariappan, Ph.D., Dept of Nat. Sci., NFC, Madison, FL. 5) Label each pair of compounds below as: a. conformational isomers b. stereoisomers ©. constitutional isomers d. identical sal eK H H 6) Apply IUPAC rules and provide a systematic name for each of the following cycloalkanes and icycloalkane: Br br. Ie ethyl—3-bepona -4-metha] (-bome ao -ethg| Cgeloherane 4 ( yotcherce veInstructor: Manoharan Mariappan, Ph.D., Dept of Nat. Sci. NFC, Madison, FL KS \Apeoeno - 1,3,3-+ Timerdnyeylogentane Morome -3-et hayl A methileyeleoer “ettid -3,4 -deme Huy legeloheplere Febhyl — fi -dimnetyleyelahicoteine What's this name? zl v > 4 ob 3 re 1-(@-dnlero - cee Ge 44 -demetlyl 104 somone Gpldeprane oes ip pes n Fncnicsnste Sagi 2 air Servo [g.4] decor belo [asd] AoNAnE \ A = 4 * at ey 4 3 s ot i eee Deeyelo (A. 2. aLundecane biewlo [s.4.0] Undecane Bt 4 ae (ae : 4 : 4 3 ei S zi 3 at ee Spice [uu] Loaded cane drexelo U.4.6) dodecane?Instructor: Manoharan Mariappan, Ph.D., Dept of Nat. Sci., NFC, Madison, FL. 7) Mlustrate two possible chair forms of (i) trans-1-sec-butyl-3-ethyl-cyclohexane and (ii) isobutyl-4-isopropyl-cyclohexane and circle the conformer that is more stable from each set, cis-1-isobutyl-4-isopropyl-cyclohexane ith aibae 8) (I) Circle which one is more stable from et pair of cha cavonnatishs and expen your, description ina few words. ke eB a 4 os : \ evwy\ vSequere sec Was Less (\3-dexa| gf Steen, Comecced o B vlowlalned mace 1,3 -deaxial shay: OAH due’ ko Phe Cray bony, (w Complete the transformation of cyclohexane conformations. Also, assign the stereoisomer (cis/tlans) of each pair of compounds. Wa ce eplecitacral pos fsa. & ws ¥ ws rea Rinctar Wann i NT ee a = LyInstructor: Manoharan Mariappan, Ph.D., Dept of Nat. Sci., NFC, Madison, FL 9) Below are the two chair conformations of a 1,2,4-trimethylcyclohexane. Estimate the amount of 1,3 4lanal strain in each conformer and prediet which conformer is most stable. } bly B only en bS-chewe i ey cH: pee ON A ae NRRL te eg ei Croan Bee ei Wee eget yeh Sis Xv Nees hoo 13 -chexin) Shey. Wns AK Cortgcernror : ‘b less Stedole clue $0 He V-dheyial steer, B ws We most sb conformer 10) On the templates provided, draw two chair conformations that are in equilibrium for Menthol as well D-pinitol. Circle the mast stable conformation. aw, M3 a ieee | J oN ec ° cH, we “MoH Bs i 3 ‘Menthol (in peppermint) 4 iM QH HCO, A OH Oy on "| F oH ‘ > ou = Ho: Ho" (OH ry a } on pinitol (antt-diabetc agent) ce SS a