Paper: Organic Chemistry

Submitted to: Sir (Amjad Sahb)

Submitted by: Muhammad Ahmad

Roll NO: 3017

Class: BS (Chem) 5th evening

Department of Chemistry

University of Okara
 Paper Organic Chemistry
Q. No. 1: Differentiate the following terms with example with Examples.
i. Differentiate between enantiomer and Diastereomers.
Enantiomers Diastereomers
These are also stereoisomers but
Enantiomers are stereoisomers that are mirror
1 they are not mirror images of each
images of each other.
other.
Have identical physical properties except for They have distinct physical
2
the ability to rotate plane-polarized light. properties.
3 They are present is pairs. They can be several molecules.

They have similar molecular shape. They have different molecular

4
shape.
Example: Example:

Both are mirror image of each other are

enantiomer.

2: Difference Between the Geometrical and optical isomerism.

Geometrical isomerism Optical isomerism

In Geometrical isomerism the molecules In optical isomerism the molecules rotate
have same structural formulas but differ in the light in one direction and the other
arrangements of groups at a single atom, at groups rotates the light in the opposite
double bond, or in rings. direction but in the same amount.
 Example: Example:
The most common example of Its example is the optical
geomatical isomerism is but-2-ene. In one isomers of amino acid alanine.
case the CH3 groups are on the opposite
sides of the double bond but in other case
they are in the same side.

Example: Example:

i. Difference Between the Cis/ trans and E/Z notation

Cis/trans notation E/Z notation

Cis/ trans isomerism is used for
1 E/Z notation is used for complex isomers.
simple isomers.
Cis/trans gives relative The E/Z system is comprehensive and
2 configuration and is not applicable provides absolute configuration of alkenes.
to all situations.
Example: Example:

So it is E Notation.

So it is Z notation

Q. No. 2:
i. What is Cahn Ingold Prelog rule:
(Ans): The CIP rule state that. (This is a standard process used in organic chemistry to give
completely and unequivocally name a stereoisomer of a molecule. The purpose of this system
is to assign an R or S descriptor to each stereocenter and an E or Z descriptor to each double
bond. So that, the configuration of the entire molecule can be determined.
These are as following:
1. The higher atomic number outranks the lower atomic number. First compare the
atomic Number (Z) of the atoms directly attached to the stereocenter (double
bond). The group having the atom of the higher atomic number will be receive
the higher priority.
2. And when the atoms are identical then compare the atoms attached to them on
the basis of their atomic number. And let’s suppose if there is tie situation then
we must consider the atoms at the distance 2 from the stereocenter as the list is
made for each group of the atoms bonded to one directly attached to the
stereocenter. Each is arranged in order of decreasing the atomic number.
3. And evaluate the substituents one by one Do no add atomic number within
groups Then the list is compared by the atom at the earliest difference the group
containing the atom of higher atomic number receive the higher priority.
4. An atom that is multiply boned to another atom will be considered to be
replicated as the substituent on that atom.
Examples: in these we follow the CIP rules and numbering them according to
their atomic number.

ii. Assign the R/S configuration to the following compounds:

Q. No. 3:
I. What is Cram’s Chelation Model? What it is used for?
(Ans) The crams rule was proposed by the Donald Cram this model was proposed for the
rationalizing the stereoselectivity of the nucleophilic additions to the carbonyl group
with the α-stereocenters. This is mainly involved in the assigning of the each α-
substituents of a relative size then placing the carbonyl oxygen antiperiplanar to the
largest of these three groups. The nucleophile then attacks the carbonyl group opposite to
the larger of the two remaining groups (medium group).

II. Using the Cram’s Model explain the most feasible site for attack of nucleophile
in the following case.
Given the fact that, H = Small group, OH = Medium group, Br = Large group
Nu = Hydride (Nucleophile).

(Ans)

Now in the structure the H is the small group OH is the medium group and Br Large
group and Nu is the Hydride (nucleophile). The oxygen of the Carbonyl will orient itself
so as to between the small and the medium sized group.
The largest being the largest group is oriented as far as possible from the carbonyl.
The nucleophile then attacks the carbonyl group opposite to the larger of the two
remaining groups (medium group).
The rule is that the incoming group PR efferently attacks on the side of the Plane
containing the small group Less hindered face.

The structure has ha chiral carbon which Is S configured.

The Nucleophile will attack Between the H and O of the carbonyl group and the
leaving group is Br