108 | organic Chemistry Topical Test 8 'Y Step-Through Questions 1. Write Fischer projections of chloro-2-butanol which represent threo-enantiomers 2. 24-diehlorohexame has tvro chiral centres. ‘Answer the folowing questions (a) How many chirality centres are in 1-bromo-3-methyieyde ee Buta? nee ei aa (0) Does it form cis-trans isomers? : Nee ca Ayes, make structures toe rant wn mel An See (© () Mark cheat centes in -bromo Snethyeyiohesane ays on r i ~cl Eine Ht. a sr fe i oe i en Ce ant ii) Witte the pair of cis-enantiomers oHcH, cH,cr4 (it) Weie the pair of trans enantiomers ‘ ¥ 4. Fill in the Blanks: om tt, Confgurationa isomers with wo citi centres are called: x ain (3) mnsif the configuration of both o he cial cece in’one isomer isthe opposite ofthe coniguaton of te IL Hy chirality centres in the other carbon. a n—-—a © se famatguatn fbr ecard ea ine ia one isomer isthe same as the configuration of ee st, Be ccsce hr Sher noe © Af one of the chirality centres has the same (@) Wire pais of enantiomers. ‘configuration in Both the isomers andthe over chicalty (©) Write pairs of stereoisomers that are diastereomers: centre has the opposite configuration in the two isomers, meee 5. Which of the following compounds has a stereoisomer thatis (6 pal of erythro enantomet yn meso.compound? @ pait of threo-enantiomers (a) 24-dibromohexane _(b) 2,4-dibromopentane (©) B4-dimethylpentane (€) 1,3-dichlorocyclohexane ; (©) Yédichlorocyelohexane (6) 1,2-dichlorocyclobatane °Y Deep Understanding 11. ‘Mark the identical structures in the following: cro ‘oH Su on 10S Moneta (CHLOH HO: H a @) oO 2 Make the Pacer pojcioos for hese conpounds Mac wh yarlcomial orem? © Gaon : t i Hy on @H=c=a Pact ““OH (©) a i ee | oH, ah oe 4 Hcg! foe ay @ — pemonon | Sco—cH =a Huot, Ho! 8, Whatis the relation between the following pairs ofstructute? iy we ‘ © ema in ant 12,it and trans designations for simple cases ate quite G Zrbutene can be cases, there are two identical substituents at each double bond. here two substituents are different, by IUPAC (E) (enigegen, opposite) 12) (zusammen, together) ae used gavier o lighter groups are on the same side, w.7 ond, we call the isomer (Z)-isomer and if one -and one heavier group ison the opposite side wr. ond, we call it (£)-isomer. For the cases high priority ow priority YN Kae low priority a & igh priority nderstanding ‘and (2) configurations of the following: Isomerism | 109 § where, 4 > B and D > C, then (a) is (Z}-isomer and (b) is (B)pisomer, 1 H_ CH; BL fis " i i on cur, a, Godt HS, HH capa cH CH, > Br>Cl CH,CH, >cH, tiem Codey Chanson . oo (2E,48)-2,4chenadiene (22,46) 2¢-hoxadiene lees Test 9 Pan a-suyhe ea be ‘he wo @) by NH, sald © by Pd—C/Hy, Cy yy) ‘ Onn Sth ongeacti a. Hs tn, Assign # and Z configurations to (A) and (B) Ae aie " 2. Write the structures of (a) @Z)-1,3-pentadiene (©) (6)-1,3-pentadiene (© QE, 48)-3-ethyl-2, 4-hexadiene (@) (22, 48)-.ethy12,4-hexadiene bf Bier is OH NH; CH, Thus, is aR Eetmothcr case withthe following amangement: T Ata Ha the bottom side by the following changes HY NH a = OHC —{-on ni Q sequence is OH > NH, -> CHO HO # [a = avy = hy 4 : H, oH? a NH, oHC—}—0H H 5 =nic mixture can be denoted by combining R and Sas in }2- butanol, 10 ane (iictN Cat, Hyc—f—08 HO—F—ch, H H 6) we ounds in which a stereogenic centre is part of @ ring are Isomerism 112 4 COH nd —_on HO 4} 1 CO.H In this, there are two chiral carbons (C, and C,). We can determine configuration of each carbon separately: ForC; © COst ol “op \ CH(OH)COOH & a WOO yf (RatC,) Semuenceis OH-+CO;II-» CHO Fore, /” GH(OB)*COOH hg vo —u “4 100,H/ boa | eae) Thus, ‘is (2R,3R)-tartaric acid COM Remember thatthe R/S, +4 and D/L nomenclatures al arse from different observations and the fact that a molecule bas, cay, the R. configuration gives no clue as to whether it will have + ot ~ optical sey eA Nevo ediatasincih oD, or += simply by working it out from the stru fey and predict wether 9 molecule will have of Specie! oration by looking atthe structure, Topical Test 10 din the same way. Configuration of. methylcyclohexene is R since a HGH lower Hy istreatedas Pre AH ep-Through Questions ssign absolute configuration as R or $ to each of the lowing compound : H B aS CtiaCHe H ) CHOH ) cH CHsCHy city 8 © ibe cscs # o Acar to112 | organic chemistry 2. Draw three-dimensfonal representations of HyGx Br 0 @ theRenantiomer of : (©) the S enantiomer af we \ x © a “Wy Deep Understanding 1. Assign Rand $ configuration tothe following: 0; ©) HN ‘cot 2. ‘OH Die al eay £03H 2. Draw three dimensional representations of each of the following stereoisomers: @) @).-2bromopentane ®) ()-3-brome-3.chlorohexane (© (-xphenyl ethylamine ; et a Asif. } a Conformations Isomers that have the same skeletons (that is, with component atoms attached in the same sequence) but differ from each other with the relative positions of some atoms in three-dimensional space by the virtue of rotation about ‘bonds are called conformational isomers or conformers. A quantitative description that relates relative atomic positions to the changes in potential energy during rotation about ao bond, describes the energetics of conformational interconversion, a process known as conformational analysis. ‘* Changing the configuration of a molecule always means thet bonds are broken, ‘+ A different configuration is different molecule, ‘© Changing the conformation of a molecule means rotating about bonds, but not breaking them. * Conformations of a molecule are readily interconvertible and ace all the same molecules, Conformers of Alkanes Rotation about (C-2C) bond in ethane can give various conformers: Hy @ W-fte oo H#——on ) obit oH Oh Hon fe i H oT T Eee @ . i cH; 2. Dra the sracrs of? trmabne and ain ‘notation of chiral centres, 4 ends “All the double bonds are cis and the absolute configuration the stereogenic centre is 5. q Write a stereochestically accurate ectocarpene. ‘5. Biological reduction of pyruvie acid gives (+) lactic acd represented by Fischer projection shown. Assign R/S ‘configuration. represdeation® 3 ; Gout cH Cc0,H —~Bablatmtvon , yo Ty Cty previ acid (9) nce at In structure 4; or B,, C—H flagpoles at C-1 completely overlap each other at C-2, This form is called eclipsed conformation. A an Hot L i al A ‘ (A) (Bi) H 4 i H a o HW 4 k (a) By)