Answer to Question #310879 in Organic Chemistry for Ravneet

Question

A pure sample of S-phenyalanine has a specific rotation of [a] of 70degree If am mixture of two enantiomers of phenylalanine gives a specific rotation of -14.0 degree, what is the percentage of S enantiomer in this mixture?

Answer 1

If a compound rotates plane polarized light in the clockwise (+) direction, it is said to be dextrorotatory, while if it rotates light in the counterclockwise (-) direction it is levorotatory. (We mentioned L- and D-amino acids in the previous section: the L-amino acids are levorotatory). The magnitude of the observed optical activity is dependent on temperature, the wavelength of light used, solvent, concentration of the chiral sample, and the path length of the sample tube (path length is the length that the plane-polarized light travels through the chiral sample). Typically, optical activity measurements are made in a 1 decimeter (10 cm) path-length sample tube at 25 °C, using as a light source the so-called “D-line” from a sodium lamp, which has a wavelength of 589 nm. The specific rotation of a pure chiral compound at 25° is expressed by the expression:

l is path length in decimeters, and c

c is the concentration of the sample in grams per 100 mL. In other words, the specific rotation of a chiral compound is the optical rotation that is observed when 1 g of the compound is dissolved in enough of a given solvent to make 100 mL solution, and the rotation is measured in a 1 dm cuvette at 25 ^oC using light from a sodium lamp.

Every chiral molecule has a characteristic specific rotation, which is recorded in the chemical literature as a physical property just like melting point or density. Different enantiomers of a compound will always rotate plane-polarized light with an equal but opposite magnitude. (S)-ibuprofen, for example, has a specific rotation of +54.5^o (dextrorotatory) in methanol, while (R)-ibuprofen has a specific rotation of -54.5^o. There is no relationship between chiral compound's R/S designation and the direction of its specific rotation. For example, the S enantiomer of ibuprofen is dextrorotatory, but the S enantiomer of glyceraldehyde is levorotatory.

A 50:50 mixture of two enantiomers (a racemic mixture) will have no observable optical activity, because the two optical activities cancel each other out. In a structural drawing, a 'squigly' bond from a chiral center indicates a mixture of both R and S configurations.