The new relationships between molecules after modifying the positions of groups is to be examined. Concept Introduction: The molecules which are non-superimposable or not identical with their mirror images are known as chiral molecules. A pair of two mirror images which are non-identical is known as enantiomers which are optically active. The objects or molecules which are superimposable with their mirror images are achiral objects or molecules and these objects have a centre of symmetry or plane of symmetry. The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds but they are optically inactive. The stereoisomers which are non-superimposable on each other and not mirror images of each other are known as diastereomers. Chiral molecules are capable of rotating plane polarized light The molecules which are superimposable or identical with their mirror images are known as achiral molecules, and achiral molecules are not capable of rotating the plane-polarised light. Plane of symmetry is the plane that bisects the molecule in two equal halves, such that they are mirror images of each other. Compounds having plane of symmetry are usually achiral as they do not have different atoms around the central carbon atom. The objects which are non-superimposable or not identical with its mirror image are known as chiral objects. The pair of two mirror images which are non-identical are known as enantiomers. The objects which are superimposable with its mirror images are achiral objects and these objects have a centre of symmetry or plane of symmetry.

Question

(a) Draw all other stereoisomers of the molecule , labelling meso forms (if any), and assign descriptors to chiral carbon atoms. (b) Including molecule below, label pairs of enantiomers and pairs of diastereomers. (c) If you were to distill a mixture of all the isomers, how many fractions could be obtained, and what is in each fraction?

Answer 1

Question

Chapter 5, Problem 3PP

Interpretation Introduction

Interpretation:

The new relationships between molecules after modifying the positions of groups is to be examined.

Concept Introduction:

The molecules which are non-superimposable or not identical with their mirror images are known as chiral molecules.

A pair of two mirror images which are non-identical is known as enantiomers which are optically active.

The objects or molecules which are superimposable with their mirror images are achiral objects or molecules and these objects have a centre of symmetry or plane of symmetry.

The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds but they are optically inactive.

The stereoisomers which are non-superimposable on each other and not mirror images of each other are known as diastereomers.

Chiral molecules are capable of rotating plane polarized light

The molecules which are superimposable or identical with their mirror images are known as achiral molecules, and achiral molecules are not capable of rotating the plane-polarised light.

Plane of symmetry is the plane that bisects the molecule in two equal halves, such that they are mirror images of each other.

Compounds having plane of symmetry are usually achiral as they do not have different atoms around the central carbon atom.

The objects which are non-superimposable or not identical with its mirror image are known as chiral objects. The pair of two mirror images which are non-identical are known as enantiomers.

The objects which are superimposable with its mirror images are achiral objects and these objects have a centre of symmetry or plane of symmetry.

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(a) Draw all other stereoisomers of the molecule , labelling meso forms (if any), and assign descriptors to chiral carbon atoms. (b) Including molecule below, label pairs of enantiomers and pairs of diastereomers. (c) If you were to distill a mixture of all the isomers, how many fractions could be obtained, and what is in each fraction?

(c) Answer the following questions: It is possible for a compound to be chiral even though it lacks a carbon atom with four different groups. Using two nitro groups, one isopropyl group and one carboxy group as substituents, draw the structure of an optically active biphenyl that is void of a chiral carbon. i. ii. Deduce, giving reasons, whether or not the following molecules are optically active. H3C CH3 ČH(CH3)2 Quaternary ammonium salt NH2 Compound A НОСІНС OCH3 OCH3 Br Compound B

(c) If the specific rotation of an enantiomeric mixture is +12.5° and that of the pure enantiomer is +50°, then what will be the % of optical purity of the dextro-isomer in the enantiomeric mixture. (i) 10% (ii) 2.5% (iii) 25% (iv) 50%