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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

Label each compound as chiral or achiral. Compounds that contain a single carbon common to two rings are called spiro compounds. Because carbon is tetrahedral, the two rings are perpendicular to each other.

a.

b.

c.

d.

The amino acid (S)-alanine has the physical characteristics listed under the structure.

a. What is the melting point of (R)-alanine?

b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine?

c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine?

d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine?

e. Label each of the following as optically active or inactive: a solution of pure (S)-alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.

Locate the stereogenic centers in each Newman projection and label each center as R or S.

a.

b.

a) Locate the stereogenic centers in the ball-and-stick model of ezetimibe (trade name Zetia), a cholesterol-lowering drug. (b) Label each stereogenic center as R or S.

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
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