Stereoisomerism

IMPORTANT

Stereoisomerism: Overview

This Topic covers sub-topics such as Optical Isomerism, Stereoisomerism, Geometrical Isomerism, Enantiomers, Diastereomers, Racemic Mixture, Types of Stereoisomerism, Configurational Isomerism and, Conformational Isomerism in Ethane

Important Questions on Stereoisomerism

EASY
IMPORTANT

What is sawhorse projection formula for conformers?

EASY
IMPORTANT

What is dihedral angle?

EASY
IMPORTANT

Define racemic mixtures.

MEDIUM
IMPORTANT

Explain how the different conformations of ethane can be obtained.

EASY
IMPORTANT

Explain the ring strain in cyclopropane molecule.

EASY
IMPORTANT

A molecule of cyclobutane adopts a _____ conformation to minimise torsional strain.

MEDIUM
IMPORTANT

Describe the conformational form of cyclobutane.

EASY
IMPORTANT

Write the formula to calculate the specific rotation of an optically active compound.

MEDIUM
IMPORTANT

Name the following alkene as per the E-Z nomenclature.

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IMPORTANT

Define configurational isomerism.

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IMPORTANT

A solution of trans-2-phenylcyclohexanol was analysed by polarimetry. At a certain concentration, the rotation angle of the solution was -5.73°. Using the calibration curve in the below figure, determine the optical purity of the sample.

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IMPORTANT

Explain how a polarimeter can be used to identify enantiomers?

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IMPORTANT

Trans-2-phenylcyclohexanol is used as a chiral auxiliary in the synthesis of anticancer drugs such as Taxol. The structure of one enantiomer of trans-2-phenylcyclohexanol is given in figure. 

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Draw the structural formula of the second enantiomer of trans-2-phenylcyclohexanol.  

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IMPORTANT

Baccatin III is the name of a biologically active compound, that can be isolated from the Pacific yew tree, Taxus bervifolia. Together with 10-deacetylbaccatin, it is a precursor of the anticancer drug Taxol. Baccatin III can be converted into 10-deacetylbaccatin by the following reaction:

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Deduce the number of chiral carbon atoms in the molecule of baccatin III.

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IMPORTANT

Taxotere (docetaxel) is an anticancer drug that can be synthesised using chiral auxiliaries. A fragment of its structure is shown in figure, deduce the number of possible stereoisomers of this structural fragment.

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IMPORTANT

Taxotere (docetaxel) is an anticancer drug that can be synthesised using chiral auxiliaries. A fragment of its structure is shown in figure, identify with asterisks (*) two chiral centres in this structural fragment.

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IMPORTANT

Parexotine, whose structure is shown below, is a drug prescribed to people suffering from mental depression.

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Identify the two chiral carbon atoms with asterisks (*).

EASY
IMPORTANT

Chirality plays an important role in the action of drugs. Describe the composition of a racemic mixture.

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EASY
IMPORTANT

Chirality plays an important role in the action of drugs. Using an asterisks (*) ,identify the chiral carbon atom in a copy of the structure of thalidomide.

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HARD
IMPORTANT

Explain the difference between conformation and configuration necessary condition for geometrical isomerism.