Welcome to

CYL 100 Chemistry

Pankaj Chauhan (Organic Chemistry)
Shivnath Mazumder (Physical Chemistry)
Subhas Samanta (Inorganic Chemistry)
 CYL 100 Chemistry

Class Schedule
Tuesday, Thursday and Friday: 12:00-1:00 PM
Help Hours: Thursday:10:00-11:00 AM

Two Minor Tests (1 hour) and One Major Examination (2 hour)

Two Surprise Quizzes

80% A A Typical Grade Distribution

70% A–
60% B Retake the major exam at the
52% B– beginning of the next semester
45% C or
38% C– This can change your grade to either D or E
30% D or
25% E Retake the entire course.
15% F
However, it may change depending on the class performance. 2
 CYL 100 Chemistry

Attendence
➢ You can miss a lecture only in case of an emergency.
➢ If the attendance falls below 80%, your grade can be decreased by one scale (e.g. A to A–).
➢ If the attendance falls below 65%, your grade can be decreased by two scales (e.g. A to B).
➢ If the attendance falls below 50%, your grade will be F.

Organic Chemistry
➢ Stereochemistry
➢ Factor Influencing Reactivities
➢ Reactivates of organic molecules
 Stereochemistry:
Geometrical Isomers

Cis-trans Isomers (Geometrical Isomers) result from the restrictic rotation caused by either
a double bond or by a cyclic structure.

The cis-isomer has the hydrogens on
the same side of the double bond,
whereas the trans-isomer has the
hydrogens on opposite sides of the
double bond.
The cis-isomer has the hydrogens on
the same side of the ring, whereas the
trans-isomer has the hydrogens on
opposite sides of the ring.

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 Stereochemistry: Isomers

Isomers Compounds that have the same molecular formula but are not identical.
Isomers:

E&Z Axial Chiralty

Constitutional or Structural isomers: Isomers differs in the way their atoms are connected.

Stereoisomers (configurational isomers) differ in the way their atoms are arranged in
space. Stereoisomers are different compounds that do not readily interconvert.
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 Stereochemistry:
Geometrical Isomers

E-Z configuration, or E-Z convention, is an extension of cis–trans isomer notation that can
be used to describe double bonds having two, three or four substituents.

➢If the two groups of higher priority are on the same side of the double bond, the bond is
assigned the configuration Z (from zusammen, the German word for "together")
➢If the two groups of higher priority are on the opposite side of the double bond, the bond is
assigned the configuration E (from entgegen, the German word for “opposite")

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 Stereochemistry:
Geometrical Isomers

Rule 1. The greater the atomic number, the higher is the priority.

Rule 2. If there is a tie, consider the atomic numbers of the atoms that are attached to the
“tied” atoms.

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 Stereochemistry:
Geometrical Isomers

Rule 3. If an atom is doubly bonded to another atom, the priority system treats it as if it were
singly bonded to two of those atoms. If an atom is triply bonded to another atom, the priority
system treats it as if it were singly bonded to three of those atoms.

Rule 4. In the case of isotopes, greater mass number, higher is the priority.

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 Stereochemistry: Chirality

• A molecule (or object) that is not superimposable on its mirror immage is said to be chiral

• A molecule (or object) that is superimposable on its mirror immage is said to be achiral
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 Stereochemistry: Asymmetric
Carbons, Chirality Centers,
& Stereocenters

Asymmetric carbon is a carbon atom that is bonded to four different groups.

chiral chiral achiral achiral

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 Stereochemistry: Isomers with
One Asymmetric Carbon

Two isomers: enantiomers

Non-superimposable mirror image molecules are enantiomers

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 Stereochemistry: Drawing
Enantiomers

Perspective or Flying Wedges Formulas

➢The solid wedges represent bonds that point out of the plane of the paper toward the viewer.

➢The hatched wedges represent bonds that point back from the plane of the paper away from the
viewer.

➢Make certain when you draw a perspective formula that the two bonds in the plane of the paper
are adjacent to one another; neither the solid wedge nor the hatched wedge should be drawn
between them.

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 Stereochemistry: Drawing
Enantiomers

Fischer Projection

➢Horizontal lines project out of the plane of the paper toward the viewer and vertical lines extend
back from the plane of the paper away from the viewer.
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 Stereochemistry: Configuration
(R & S)

Configuration is the relative position of the atoms in a molecule that can be changed exclusively
by cleaving and forming new chemical bonds

(R) Rectus = "right" (S) Sinister = "left“

00
00

1
1

2 (S) 4 4 (R) 2

3 3
 Stereochemistry: Configuration
(R & S)

➢Isotopes
➢Double and triple bonds

➢Geometric Isomers: (E & Z)

(E) Entgegen = Opposite higher priority groups are on opposite sides of the double bond.

(Z) Zusammen = Together higher priority groups are on the same side of the double bond.

(E)
(Z) Gets more priority than (E)
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(Z)
 Stereochemistry: Configuration
(R & S)

1 1

(R) (S)
3 2 2 3

4 4

3
3

1
1 4
4 (R)
(S)

2
2

2 2

3 4
4 3 (R)
(S)

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1 1
 Stereochemistry: Compunds with
Two Asymmetric Carbon

A compound can have 2n stereoisomers

n = no. of stereocentes

Diastereomers are stereoisomers that are not enantiomers 17

 Stereochemistry: Compunds with
Two Asymmetric Carbon

Newmann Projection

Eclipsed Gauche Partially Eclipsed Staggered

Sawhorse Projection

Eclipsed Gauche Partially Eclipsed Staggered

Conformation is the set of possible shapes a molecule can have by means

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of rotation about single bonds only.
Stereochemistry: Compunds with
Two Asymmetric Carbon

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 Stereochemistry: Compunds with
Two Asymmetric Carbon

A meso compound is a molecule with multiple stereocenters that is

superimposable on its mirror image due to the presence of plan of symmetry.
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Stereochemistry: Compunds with
Two Asymmetric Carbon

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Stereochemistry: Compunds with
Two Asymmetric Carbon

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Stereochemistry : Drawing
Enantiomers

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 Stereochemistry: Optical Acitivity

➢ Physical properties of enantiomers are the same.

➢ Enantiomer beaves differently with polarized light.

➢ An achiral compound does not rotate the plane of polarization. It is optically inactive.
➢ A chiral compound rotates the plane of polarization. A chiral compound will rotate the plane
of polarization clockwise or counterclockwise.

Dextrorotatory, indicated by (+) or D Devorotatory, indicated by (-) or L

➢ A compound that rotates the plane of polarization is said to be optically active.

➢ chiral compounds are optically active and achiral compounds are optically inactive.
Polarimeter

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 Stereochemistry: Optical Acitivity

The specific rotation is the number of degrees of rotation caused by a solution of 1.0 g of
the compound per mL of solution in a sample tube 1.0 dm long at a specified temperature
and wavelength.

Degree dm-1g-1mL

2-Methyl-1-butanol

A mixture of equal amounts of two is called a racemic mixture or a racemate.

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 Stereochemistry: Optical Acitivity

➢ Enantiomeric excess (ee) is a measurement of purity used for chiral substances.

➢ Reflects the degree to which a sample contains one enantiomer in greater amounts
than the other.

➢ A racemic mixture has an ee of 0%, while a single completely pure enantiomer has an
ee of 100%. A sample with 70% of one enantiomer and 30% of the other has an ee of
40% (70% − 30%).

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 Chirality in Systems Lacking
Chiral Centres: Axial Chirality

Axial chirality is a special case of chirality in which a molecule does not possess a
stereogenic center but an axis of chirality an axis about which a set of substituents is held in a
spatial arrangement that is not superimposable on its mirror image.

➢ Axial Chirality in Allenes

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Chirality in Systems Lacking
Chiral Centres: Axial Chirality

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 Chirality in Systems Lacking
Chiral Centres: Axial Chirality

Atropisomeric biaryl compounds wherein the rotation about the aryl-aryl bond is restricted.

➢ Bulky ortho substituents ➢ Different ortho substituents

(S)

(R)

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 Stereochemistry: Biomolecules,
Receptors and Drugs

DNA Protein Carbohydrates

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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Beckmann Rearrangement

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 Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

Caprolactam:

Global demand for this compound is approximately 5 million tons per year, and the vast
majority is used to make Nylon 6 filament, fiber, and plastics.
Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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Stereochemistry: Baeyer Villiger
Oxidation ecules

t-Bu > i-Pr = Ph > Et > Me

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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 Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

Paracetamol: also known as acetaminophen or APAP, is a medicine used to treat pain and fever

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 Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

Aspirin: Medication used to treat pain, fever, or inflammation

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Stereochemistry: Discrimination of
Enantiomers by Biological Molecules

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