Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

Organic Chemistry

IIT JAM : Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

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Sawhorse Representation

The sawhorse formula indicates the spatial arrangement of all the groups on two adjacent carbon atoms is represented by a diagonal line usually from lower left to upper right. 

  • The left handed bottom end represents the atom nearest to the observer and the right-hand top end represents the atom away from the observer. 
  • Two of the remaining bonds to the two atoms are drawn vertically and other four at +1200 and-1200 angles.

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

Newman Projection

The Newman projection formula is the planar projection formula of the sawhorse formula.

  • Newman projection is similar to the sawhorse projection but represents the spatial arrangements of all the groups on the two carbon atoms. 
  • Here, a molecule is viewed along the axis of a carbon-carbon bond. The carbon towards the front is represented by a dot (.) and the carbon towards the rear by a circle.

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

Fischer Projection (2-D representation)

The Fischer projection, devised by Emil Fischer in 1891, is a two-dimensional representation of a three-dimensional organic molecule by projection. 
  • Horizontal bonds: Points towards the observer
  • Vertical bonds: Points away from the observer

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

Some Important Rules

In order to find out whether the two structures are identical or not, these projections can be manipulated only in specific ways. The following rules must be obeyed.

1. For comparison, a fischer projection may be rotated 180° in the plane of the paper & molecule remains same.

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

2. One interchange in the fischer projection leads to the enantiomers. Configuration at the

stereocenter changes from (S) to (R) and vice-versa.

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

3. Two or any even number of interchanges of the groups at the chiral centre, don’t changes the configuration.

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

4. A 900 rotation of the fischer projection formula about the chiral centre inverts the configuration.

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

5. It is not permitted lift projection formulae out of the plane of the paper and flip them over or view them from the opposite side of the paper. These operations, if done, are the same as breaking a bond to change the configuration of the original molecule.

For Example:

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

6. Fischer projection can be manipulated by rotating a group of any three ligands in a clockwise or anticlockwise direction; the fourth ligand doesn’t change its position (Such a manipulation is equivalent to two interchanges).

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

Flying–Wedge Representation (3-D representation)

The Flying-Wedge Projection is the most widely used three-dimensional representation of a molecule on a two-dimensional surface (paper). 
This kind of representation is usually done for a molecule containing a chiral centre. In this type of representation three types of lines are used. 
  • Solid wedge (thick line)- bond above the plane of paper
  • Broken wedge (dashed line) – a bond below the plane of the paper
  • Continuous lines (solid lines)- bonds in the plane of the paper

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

Interconversions
Fischer Projection into Flying Wedge and Vice-Versa

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

  • We draw the bonds which are towards the observer by solid wedge and the bonds away from the observer by dashed lines. Then the above-shown molecule becomes.

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

  • We want to convert this molecule into flying wedge projection formula for this hold the atom C and D and starts the process of bending so that an inverted V is formed i.e.^. This inverted v represents the atoms in one plane. Now draw the B below this plane which is shown below in this formula.
  • The atom shown above is represented above the plane in the flying wedge formula.
  • We are observing from the bottom of the right side. If we will observe from top of this molecule then we find that

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

Conversion of Fischer Projection into Sawhorse and Newman Formula

  • If we want to convert eclipsed form of flying wedge projection into a staggered form then hold C2 atom in hand in its position and rotate the C3 atom by 1800
  • The atoms which are towards the observer are away from the observer and the atoms which are away from the observer become towards the observer.

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

i. Eclipsed conformation (Flying wedge projection).

ii. Eclipsed conformation (Fischer projection).

iii. Staggered conformation (Flying wedge projection).

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRevSawhorse into Fischer Conversion

Sawhorse Formula into Newman Projection Formula

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRev

  • We know that the left-handed bottom end is towards the observer and right-hand top end is away from the observer. 
  • We can convert this formula into Newman formula representing the molecule i.e. C2 which is towards the observer by a dot (.) and the atom which is away from m the observer that is C3 by a circle.
  • The Newman projection formula is a planar projection of the sawhorse formula. In this molecule, we view along with the carbon-carbon bond. 
  • The carbon atom towards the observer is represented by a dot (.) and the carbon atom away from the observer is represented by a circle. 
  • The above shown eclipsed form can be converted into staggered form by a rotation of 1800 of one carbon atom only.

Realistic Representation Of Stereo Structures Of Molecules - Stereochemistry Chemistry Notes | EduRevConversion of Fischer Projection into Sawhorse Projection via Newmann Projection

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