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CHEMQUEST STUDY CENTRE

STERIOCHEMISTRY
MODERN TERMINOLOGY

ACCORDING TO THE SYLLABI OF CALCUTTA UNIVERCITY

FIRST YEAR

2012

CONTACTs
Mridul Ahamed Mob: 9830440993 Dr. Bellal Ali Mob: 9830440886

E-Mail: chemquest2011@gmail.com Co-operated by

AL-HILAL MISSION
(An Educational, Cultural & Social Welfare Organization) Kadambagachhi ,Barasat, Kolkata-7000125

189-PARK

CIRCUS(7POINT,NEAR

ARSALAN)

KOLKATA-17

Three-Dimensional Representations
There are two main categories of molecules, those that are in a straight-chain, or acyclic, form, and those that are in a ring, or cyclic, orientation. The following pages will give information on the different structural notations, so that more complex molecules can be compared in later sections.

Straight-Chain Structures 1. Wedge-Dash Notation 2. Newman Projections 3. Sawhorse Projections 4. Fischer Projections

Three-Dimensional Representations: Straight-Chain Structures

CH3
Br CH3 H

COOH HO HO H CH 2OH H H OH Br H H H3C

Br H

Cl

CH3

CH3 CH3

Br

There are four main types of representations for straight-chain molecules, as shown above. From left to right, these structures are the Wedge-Dash, the Newman Projection, the Fisher Projection, and the Sawhorse Projection

Flying-Wedge or Wedge-Dash projection

The Flying-Wedge projection is the most common three-dimensional representation of a three dimensional molecule on a two dimensional surface (paper). This kind of representation is usually done for molecules containing chiral centre. In this representation, the ordinary lines represent bonds in the plane of the paper. A solid Wedge ( ) represents a bond above the plane of the paper and a dashed wedge ( ) or a broken line ( ) represents a bond below the plane of the paper. The Flying-Wedge projection formula of (R)- Lactic acid , for example, can be shown as follows..

H3C
bonds in the plane of the paper
bond bellow the plane of the paper

OH H3C H
bond above the plane of the paper

(R) - Lactic acid

Newman Projections
Newman Projections are used mainly for determining conformational relationships. Recall that conformers are molecules that can be converted into one another by a rotation around a single bond. Newman Projections are also useful when studying a reaction involving prochiral molecules that have a double bond, in which the addition of a new group creates a new stereocenter. In this notation, you are actually viewing a molecule by looking down a particular carbon-carbon bond. The front carbon of this bond is represented by a dot, and the back carbon is represented by a large circle. The three remaining bonds are drawn as sticks coming off the dot (or circle), separated by one another by 120 degrees. A Newman Projection can be drawn such that the groups on the front carbon are staggered (60 degrees apart) or eclipsed (directly overlapping) with the groups on the back carbon. Below are two Newman Projections of ethane, C2H6. The structure on the left is staggered, and the structure on the right is eclipsed. These are the simplest Newman Projections because they have only two carbons, and all of the groups on both carbons are identical.
H

H H H H H

H H

Eclipsed

Staggered

Adding more carbons makes Newman Projections more complicated. For example, Newman Projections can be made for butane, such that its eclipsed, gauche, and anti conformations can be seen. (Recall that these three forms of butane are conformational isomers of one another.) In this case, the front dot represents the second carbon in the butane chain, and the back circle represents the third carbon in the butane chain. The Newman Projection condenses the bond between these two carbons.

CH3 CH3 H H H H H

CH3 CH3 H H H H

CH3 H H CH3

Eclipsed

Gauche

Staggered

Sawhorse Projections
Sawhorse Projections are very similar to Newman Projections, but are used more often because the carbon-carbon bond that is compressed in a Newman Projection is fully drawn out in a Sawhorse Projection. When properly laid-out, Sawhorse Projections are useful for determining enantiomeric or diasteromeric relationships between two molecules, because the mirror image or superimposibility relationships are clearer. Like with Newman Projections, a Sawhorse Projection is a view of a molecule down a particular carboncarbon bond, and groups connected to both the front and back carbons are drawn using sticks at 120 degree angles. Sawhorse Projections can also be drawn so that the groups on the front carbon are staggered (60 degrees apart) or eclipsed (directly overlapping) with the groups on the back carbon. Below are two Sawhorse Projections of ethane. The structure on the left is staggered, and the structure on the right is eclipsed. These are the simplest Sawhorse Projections because they have only two carbons, and all of the groups on the front and back carbons are identical.

H H H H H H H H H H

H H

Adding more carbons makes Sawhorse Projections slightly more complicated. As with Newman Projections, Sawhorse Projections can be made for butane, such that its eclipsed, gauche, and anti conformations can be seen. (Recall that these three forms of butane are conformational isomers of one another.) Notice that is much easier to determine the number of carbons in the longest chain using Sawhorse Projections than it is for Newman Projections because the carbon-carbon bond between the second and third carbons is drawn out.

H3C H3C H H H3C H Gauch H H

H3C H H

H3C H

H CH3

H Eclipsed

Staggered

Fischer Projections
The Fischer projection, devised by Hermann Emil Fischer in 1891, is a two-dimensional representation of a three-dimensional organic molecule by projection. Fischer projections were originally proposed for the depiction of carbohydrates and used by chemists, particularly in organic chemistry and biochemistry. The use of Fischer projections in non-carbohydrates are discouraged, as such drawings are ambiguous when confused with other types of drawing.

CH3 H HO HO CH3 OH H H

Fischer Projections are used often in drawing sugars and hydrocarbons, because the carbon backbone is drawn as a straight vertical line, making them very easy to draw. When properly laid-out, Fischer Projections are useful for determining enantiomeric or diasteromeric relationships between two molecules, because the mirror image relationship is very clear. In a Fischer Projection, each place where the horizontal and vertical lines cross represents a carbon. The vertical lines are actually oriented away from you (similar to dashes in the Wedge-Dash Notation) and the horizontal lines are oriented toward you (similar to wedges in the Wedge-Dash Notation).

HO Br HO Cl H3C Br that u see.... OH Br CH3 Cl CH3 Cl

just copy this on ur page ...... u will get the fischer projection

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