The concentration of cholesterol dissolved in chloroform is \(6.15 \mathrm{~g}\) per \(100 \mathrm{ml}\) of solution. (a) A portion of this solution in a 5 -cm polarimeter tube causes an observed rotation of \(-1.2^{\circ}\). Calculate the specific rotation of cholesterol. (b) Predict the observed rotation if the same solution were placed in a \(10-\mathrm{cm}\) tube. (c) Predict the observed rotation if \(10 \mathrm{ml}\) of the solution were diluted to \(20 \mathrm{ml}\) and placed in a \(5-\mathrm{cm}\) tube.

Short Answer

Expert verified
The specific rotation of cholesterol is \(-39.022^\circ \mathrm{dm}/\mathrm{g}\cdot\mathrm{ml}\). When placed in a 10-cm tube, the observed rotation is -2.4°. If 10 ml of the solution is diluted to 20 ml and placed in a 5-cm tube, the observed rotation is -0.6°.

Step by step solution

01

Find the concentration of the solution in g/ml

First, let's find the concentration of cholesterol in the solution. We know that 6.15 g of cholesterol is dissolved in 100 ml of solution. To find the concentration in g/ml, we can divide 6.15 g by 100 ml: \(c = \frac{6.15 \mathrm {~g}}{100 \mathrm {~ml}} = 0.0615 \mathrm {~g/ml}\)
02

Calculate the observed rotation for the 5-cm tube

We are given that the observed rotation in the 5 -cm polarimeter tube is -1.2°.
03

Calculate the specific rotation

Now we can use the formula for specific rotation to find the specific rotation of cholesterol: \[ [\alpha] = \frac{\alpha obs}{(l*c)}\] where \([\alpha]\) is the specific rotation, \(\alpha_{obs}\) is the observed rotation, \(l\) is the length of the polarimeter tube in decimeters (dm), and \(c\) is the concentration of the solution in g/ml. First, we need to convert the tube length from cm to dm: \(l = \frac {5 \mathrm {~cm}}{10 \mathrm {~cm/dm}} = 0.5 \mathrm {~dm}\) Now, we can calculate the specific rotation: \([\alpha] = \frac {-1.2^\circ}{0.5 \mathrm {~dm} * 0.0615 \mathrm {~g/ml}} = -39.022^\circ \mathrm {dm} / \mathrm {g} \cdot \mathrm {ml}\] Therefore, the specific rotation of cholesterol is -39.022° dm/g·ml.
04

Predict the observed rotation for the 10-cm tube

For part (b), we need to find the observed rotation when the solution is placed in a 10-cm tube instead. We can rearrange the specific rotation formula to solve for the observed rotation: \(\alpha_{obs} = [\alpha] * (l*c)\) We need to convert the tube length from cm to dm: \(l = \frac {10 \mathrm {~cm}}{10 \mathrm {~cm/dm}} = 1 \mathrm {~dm}\) Now we can calculate the observed rotation: \(\alpha_{obs} = -39.022^\circ \mathrm {dm} / \mathrm {g} \cdot \mathrm {ml} * (1 \mathrm {~dm} * 0.0615 \mathrm {~g/ml}) = -2.4^\circ\) So, the observed rotation in the 10-cm tube is -2.4°.
05

Calculate the observed rotation for the diluted solution in a 5-cm tube

For part (c), we need to find the observed rotation when 10 ml of the solution is diluted to 20 ml and placed in a 5-cm tube. First, we need to calculate the new concentration after dilution. Since the volume is doubled but the amount of cholesterol remains constant, the new concentration is half of the original concentration: \(c_{new} = 0.0615 \mathrm {~g/ml} * \frac {1}{2} = 0.03075 \mathrm {~g/ml}\) Now, we can use the formula for observed rotation with the new concentration and the 5-cm tube length (already converted in Step 3): \(\alpha_{obs, new} = -39.022^\circ \mathrm {dm} / \mathrm {g} \cdot \mathrm {ml} * (0.5 \mathrm {~dm} * 0.03075 \mathrm {~g/ml}) = -0.6^\circ\) So, the observed rotation for the diluted solution in a 5-cm tube is -0.6°.

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Most popular questions from this chapter

Which of the following formulas are chiral? (a) 1-chloropentane (e) 2 -chloro-2-methylpentane (b) 2 -chloropentane (f) 3 -chloro-2-methylpentane (c) 3-chloropentane (g) 4-chloro-2-methylpentane (d)1-chloro-2-methylpentane (h) 1-chloro-2-bromobutane

Neglecting stereoisomers for the moment, draw all isomers of the formula \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{DCl}\). (b) Decide which of these are chiral.

Isopentane is allowed to undergo free-radical chlorination, and the reaction mixture is separated by careful fractional distillation. (a) How many fractions of formula \(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{CI}\) would you expect to collect? Draw structural formulas, stereochemical where pertinent, for the compounds making up each fraction. Specify each enantiomer as \(\mathrm{R}\) or \(\mathrm{S}\). (b) Which if any, of the fractions, as collected, would show optical activity? Account in detail for the optical activity or inactivity of each fraction.

Give the stereoisomers of: (a) 2 -butene (d) 1-bromo-1-chloropropene (b) 2 -pentene (e) 2-bromo-1-chloropropene (c) 2,4 -hexadiene (f) 1 -bromo-1,2-dichloroethene Indicate for each the isomer that is expected to predominate in an equilibrium mixture. Justify your answer.

On treatment with permanganate, cis-2-butene yields a glycol of m.p. \(34^{\circ}\), and trans-2-butene yields a glycol of m.p. \(19^{\circ}\). Both glycols are optically inactive. The glycol of m.p. \(19^{\circ}\) is resolvable (through reaction with optically active salts) into two fractions of equal but opposite rotation. The glycol of m.p. \(34^{\circ}\) is not. (a) What are the configurations of the two glycols? (b) Assuming these results are typical (they are), what is the stereochemistry of hydroxylation with permanganate? (syn or anti?) (c) Treatment of the same alkenes with peroxy acids gives the opposite results: the glycol of m.p. \(19^{\circ}\) from cis-2-butene, and the glycol of m.p. \(24^{\circ}\) from trans-2- butene. What is the stereochemistry of hy droxylation with peroxy acids?

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