Question

Enariurners have very similar physical properties, while for diastercorrere they can be very dillereril. This lecl is important in the separation or resolution of charliners. In the lecture, we looked al how chiral chromatography is used to separate enantiomers: first, by reacting them with an optically pure chiral reagent (i.e., pure 2 or 5) to form a pair of diastereomers, then separating them using chiral chromatography, and finally detaching the chiral rcaycrillo recover the now separated enantiomers. An alternative bulless common means el sepurating the ciastercomers is replacing the chiral chromatography step with distillation. Recall that distillation separates solution components based on their clifferences in boiling points a physical property. An excess cl a recernic mixture of 2-chloropropanoic acict is rected with 1 91-2-tricthyl-1-butanol, converting it to the ester 2-methylbutyl 2. chloropropanoale. As part of the problem, nu wedges or hushed bonds are shown. OH (S) 2-methyl-butanol OH 2-chloropropanole all 2-methylbutyl 2-chlorpropanoale (tacemic mixture, in excess) The reactor mixture is the subjected lo carclul distillation. Three fractions are oblined, and two of them arc opucally active (Actually, in reality, all three Iructions will be optically active, but for this problem we may choose to ignore this fact. What compound or compounds constitute each of these fractions?

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Enantiomers have very similar physical properties, while for diastereomers they can be very different. This fact is important in the separation or resolution of enantiomers. In the lecture, we looked at how chiral chromatography is used to separate enantiomers: first, by reacting them with an optically pure chiral reagent (i.e., pure R or S) to form a pair of diastereomers, then separating them using chiral chromatography, and finally detaching the chiral reagent to recover the now-separated enantiomers. An alternative but less common means of separating the diastereomers is replacing the chiral chromatography step with distillation. Recall that distillation separates solution components based on their differences in boiling points (a physical property).
An excess of a racemic mixture of 2-chloropropanoic acid is reacted with ( S)-2-methyl-1-butanol, converting it to the ester 2-methylbutyl 2-chloropropanoate. As part of the problem, no wedges or hashed bonds are shown.

The reaction mixture is then subjected to careful distillation. Three fractions are obtained, and two of them are optically active. (Actually, in reality, all three fractions will be optically active, but for this problem we may choose to ignore this fact.) What compound or compounds constitute each of these fractions?