Question

Only need help with 1B) please show step by step process, I'm not sure how to approach this type of question

1. The compound D-(-)-malic acid is a key component of the metabolic process known as the Krebs cycle; it occurs to a significant extent in apples, and is responsible for much of the taste of the rhubarb plant. Its structure is shown as the Fischer projection on the right: CH2COH H- OH COH A 1.0 gram sample of the naturally-occurring material, if dissolved in 1.0 mL of water and placed in a 1.0 dm tube will cause a deviation of 27 degrees in the plane of plane-polarized light. a) Would D-(-)-malic acid be classified as 'R' or 'S' in the Cahn-Ingold-Prelog system of specifying absolute configuration? (4 points) b) An attempted laboratory synthesis of the material in its naturally-occuring form resulted in the formation of that isomer in a ratio of 4-to-1 relative to its enantiomer; what would be the value for ( a ) for that synthetic sample? (show your answer on line to the right; show your work below) (6 points)

Answer 1

1. 
   b) Specific mdatin t is the optial ofatin Comtentnated soltion ohen pah gh will be 10 cm/1 dm at a partoular wavelength optial of Potation where a Clonc. of soluhon Now 2 data, Cin dm) =Apecifie rotation or=27 CE mL 1 X1 en antomerie excess/optial puriky 4t is how much one enantomer is ex cess bnesent cmped to other enantiomer in miyhre Obviousyophieal rota tion f the miyhre wll dfe fomopheal uta thn the myhure afned enantomer the enantomer contair both two enantiomer4 of DE maleic acid New, the 91ahio : enantiomerit extess 1 4+1 So, 60 enantomeuc exces (ee) of DE)malee acid means 60%, D-)-maleic acid+ ho naceimic mihore
   
   m that 407 91aceme mixture 20% is D6)-malei another -enantisme atd and 20 Then oatio 2 enantiomen Go+ 20) : 20 80 : 20 4:| 17 of Dmaleic acid 8 60% ee Novw, eptical mota tion thet amithett (ehautimere ample excess parhicular enantiomer that X specific motatisn enantiomes)o 100 pure 60 x6279 = + 16.0 mixhure loD ample) o 16. 2 fm the syitee sample ]-,16-2"
   
   Would be (R) and if 23 is aild be s) anticlockwise then the bon the ofther side if 4th positiov h09izantal line then ise i's in we check 23 clock way) )-comfuain anti-elo ckwise in the simila 23 clockw'se 2-3anti- clock wise- OP here Cor molecule Now We See our ing gg prinetyh the - OH COOH- CooH H(aeCo9rc CH2 COOH H to tahn-ngeld rele ule) .4 Tlp CooH 3 OH 4- eooH a 2 130 th we Con see foom find side 123clockurse and 4 posihen eup is m hizantal position th Co, wl be )-erntion Cf/
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   Would be (R) and if 123is aild be s) anticlockwise then the bon the ofther sideif 4th positiov h09izantal linethen i's in we check 23 clock wa) )-comfuain anti-elo ckwise (in the simila 23 clock w'se I2-3anti- clock wise ise Op here COn Cor molecule Now We See our in giing prinhy - OH COOH- CooH H(aeCo 9rc to the CH2 COOH H to can-gld ela mle) cooH 3 OH 4- CooH d2 3 th we Con see fom find side 123 clockurise and 4 positen eup is m hizantal position Co, wlbe ()-erntion th Df/
   
   )Aonng CH2COH the 4 differe ro up's attached with ehinal iven uasty COOH Carbon atom ane their D-6)-malic aeid onatomicmurnber higher depeuds chaining aom getin F toe saletire prionhy 5the finst atom, we leok fer second atom. the hhigh atprnie no. is not deeided rojection In Fiseher 2 -3 3- 4 4 (S) 4 (R) - 1 (-fatin Now, in fischer pojechen, at fnst ionity to the gaups present and Jeast troty noup ( oup)is n the vertieal Jine 0r in hopizantal line. paston roup we are See if the a) If th is in vertital ine then and if t is clockwse then we See 12-3 1/1