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Chapter 5: Q.29 (page 200)

A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of water. What is the specific rotation of this compound?

Short Answer

Expert verified

The specific rotation is +100°.

Step by step solution

01

Specific rotation

Specific rotation comes from the interaction of the chiral compound with monochromatic light.

Every chiral compound has its tendency for plane-polarized light’s rotation, and it depends upon the concentration of the sample, length of the corresponding tube, and the observed rotation.

02

Formula to calculate the specific rotation    

The formula to calculate the specific rotation is as follows:

α=αl×c

Where,αis the specific rotation,

αis the observed rotation,

l is the length of the tube,

c is the concentration of the sample.

03

Explanation

The given data is:

αis +10°.

l is 1 dm.

c is the 1g10mL.

Therefore, the specific rotation is calculated as follows:

α=10°1×1g10mL=+100°

Therefore, the specific rotation is +100°.

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Most popular questions from this chapter

Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopenatane.

  1. How do the boiling points of A and B compare? What about A and C?
  2. Characterize a solution of each of the following as optically active or optically inactive: pure A; pure B; pure C; an equal mixture of A and B; an equal mixture of A and C.
  3. A reaction forms a 1:1:1 mixture of A, B, and C. If this mixture is distilled, how many fractions would be obtained? Which fractions would be optically active and which would be optically inactive?

A limited number of chiral compounds having no stereogenic centers exist. For example, although A is achiral, constitutional isomer B is chiral. Make models and explain this observation. Compounds containing two double bonds that share a single carbon atom are called allenes. Locate the allene in the antibiotic mycomycin and decide whether mycomycin is chiral or achiral.

HC≡C-C≡C-CH=C=CH-CH=CH-CH=CH-CH2CO2H

A sulfonium ion (R3S+) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an R or S designation to sulfur, the lone pair is always assigned the lowest priority (4). SAM, S-adenosylmethionine, is a biologically active sulfonium ion that we will learn about in Section 7.16. Locate all the stereogenic centers in SAM, and assign an R,S designation to each center.

The facts in Section 5.4A can be used to locate stereogenic centers in any molecule, no matter how complicated. Always look for carbons surrounded by four different groups. With this in mind, locate the four stereogenic centers in aliskiren, a drug introduced in 2007 for the treatment of hypertension.

How is each compound related to the simple sugar D-erythrose? Is it an enantiomer,diastereomer, or identical?

a.

b.

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