Organic Chemistry
Chirality
Chirality
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<strong>Organic</strong> <strong>Chemistry</strong> - Ch 11 551 Daley & DaleyO1)MgBrHO2) H 3 O+OHRacemic2-phenyl-2-butanolExercise 11.5A series of solutions contains mixtures of the two enantiomers of 2-bromobutane. The specific rotations for these compounds are +39.4 ofor the d isomer and –39.4 o for the l isomer. Calculate the observedrotations of [α] using a 1 dm cell at 25 o C for each of the followingsolutions.a) 0.1 g/mL of d and 0.1 g/mL of lb) 0.01 g/mL of d and 0.1 g/mL of lc) 0.5 g/mL of d and 0.3 g/mL of ld) 1.0 g/mL of d and 1.5 g/mL of lSample solutionb) The rotation of the d isomer isFor the l isomer, the rotation is= 39.4 o x 1 x 0.01= 0.394 o= –39.4 o x 1 x 0.1= –3.94 oBecause the observed rotation would be the sum of the two, then= 0.394 o + (–3.94 o )= –3.55 o11.5 Fischer Projectionswww.ochem4free.com 5 July 2005