CY101: Engineering Chemistry

Dr. Vivek Gupta

Department of Applied Chemistry
School of Vocational Studies and Applied Sciences (SoVSAS)
Gautam Buddha University, Greater Noida, U.P.

Representations of 3 dimensional structures

The three-dimensional (3-D) structure of organic molecules can be represented on paper
by using certain conventions. For example, by using solid ( ) and dashed ( ) wedge
formula, the 3-D image of a molecule from a two-dimensional picture can be perceived.

( ) indicate a bond projecting out of the paper and towards the observer

( ) indicate a bond projecting out of the paper and away from the observer
Flying-Wedge Projection: 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 molecule containing chiral centre. In this type of representation
three types of lines are used; solid, dashed and plane line.

Sawhorse projection: A representation of molecular structure, from an oblique angle (similar to

zig-zag projections).

C-C = 1.54 Å
C-H = 1.10 Å
H-C-H = H-C-C = 109.5˚

Sawhorse representation for the 2-Butanol

Newman projection:

 visualizes the conformation of a chemical bond from front to back

 front atom represented by a dot
 back carbon as a circle
 This type of representation clearly illustrates the specific dihedral angle between the
proximal and distal atoms.
 Staggered Eclipsed

Fisher Projection: a two-dimensional representation of a three-dimensional organic molecule by

projection
 Configurations
Configuration is the precise arrangement of groups around a stereogenic centre.

Rotates the the plane of polarized light in a clockwise direction, then it becomes + lactic acid

Absolute configuration which is the precise arrangement of groups around a stereogenic centre
has been introduced. This is only obtained by single crystal X-ray crystallography.

DL nomenclature system:

Glyceryldehyde

Heteroatom, that means the -OH is on the right side, that will be called D configuration.

Heteroatom, that means the -OH is on the left side, that will be called L configuration.

R/S configuration

Cahn-Ingold-Prelog priority rules,

The four nonidentical ligand atoms are assigned a decreasing priority 1 > 2 > 3 > 4.
The molecule is then viewed opposite from the lowest-priority group, that is, the group is placed
behind the stereocenter and away from the viewer.

Two arrangements are possible, the groups can decrease in priority in either (i) a clockwise (ii) a
counterclockwise direction.

The clockwise direction configuration is assigned R (for rectus) and the counterclockwise
direction is assigned S (for sinistre).
Conformations of butane:
Two hydrogen atoms in ethane replaced by larger methyl groups.
Steric factors becomes a significant contribution to the rotational energy barriers.
The six conformations that butane can adopt as the central C–C bond is rotated in 60° intervals
are shown below.
Each of the eclipsed conformations will be energy maxima but the syn-periplanar conformation
(q = 0°) will be higher in energy than the two anticlinal conformations (q = 120° and 240°): in
the syn-periplanarconformation two methyl groups are eclipsing each other whereas in the
anticlinal conformations each methyl group is eclipsing only a hydrogen atom. The staggered
conformations will be energy minima but the two methyl groups are furthest from each other in
the anti-periplanar conformation so this will be a slightly lower minimum than the two synclinal
(gauche) conformations.

As in ethane, the eclipsed conformations are not stable since any rotation leads to a more stable
conformation. The staggered conformations are stable since they each lie in a potential energy
well. The anti-periplanar conformation, with the two methyl groups opposite each other, is the
most stable of all. We can therefore think of a butane molecule as rapidly interconverting
between synclinal and anti-periplanar conformations, passing quickly through the eclipsed
conformations on the way. The eclipsed conformations are energy maxima, and therefore
represent the transition states for interconversion between conformers.
Slow down the rapid interconversions in butane (by cooling to very low temperature, for
example), we would be able to isolate the three stable conformations—the anti-periplanar and the
two synclinal conformations. These different stable conformations of butane are some sort of
isomers. They are called conformational isomers or conformers.