Chemical Reactions,
Stereochemical aspects
Lecture by Kalpajyoti Dihingia
Department of Chemistry
DHSK college, Dibrugarh
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Stereochemical aspects of nucleophilic
substitution reaction
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SN2 reaction proceeds with complete
stereochemical inversion while SN1 Reaction
proceeds with racemisation.
●
In order to understand this concept, we need to
learn some basic stereochemical principles and
notations - ( optical activity, chirality, retention,
inversion, racemisation, etc )
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Plane polarised light and optical
activity
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Compounds which can rotate the plane polarised
light(produced by passing ordinary light through
nicol prism) when it is passed through the solutions.
Such compounds are called optically active
compounds.
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Optical activity
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If the compound rotates the light to right, i.e
clockwise direction,it is called dextrorotatory or d
form, indicated by (+) sign.
●
If the compound rotates the light to left, i.e
anticlockwise direction, it is called laevorotatory
or the l-form, indicated by (-) sign
●
Such (+) and (-) isomers are called as optical
isomers.
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Molecular asymmetry, chirality
and enantiomers
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The difference in optical activity is associated with 3-
D arrangements of atoms( configurations)
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If the 4 groups arround a central C atoms are
different, such C is called asymmatric C or
stereocenter
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Superimposable objects
Note:
Superimposable objects: Achiral
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Non-superimposable objects
Note:
Non-superimposable
- chiral, chirality
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Chiral molecule
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Stereoisomers related to each other as a
superimpossable mirror images are called
enantiomers
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Racemisation
●
A mixture containing equal proportion of
enantiomers have zero optical rotation.
– Because rotation due to one isomer will be
cancelled by the rotation due to other isomer.
– Such a mixture is called racemic mixture or
racemic modification.
– A racemic mixture is represented by dl or (+_)
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Retention of configuration
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It is the preservation of integrity of the spatial
arrangement of bonds to a asymmetric cnter
during a chemical reaction or transformation.
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Home work
●
Explain the SN1 and SN2 mechanism taking
examples of optically active alkyl halides.
Submit the answer in google
classroom.
●
Due date- 10th oct 11.59 pm
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Elimination reaction
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There is elimination of H from ¯ carbon atom.
Therefore it is often called ¯ elimination.
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If more than one ¯ - hydrogen is available,
usually one alkene is formed as a major product.
Follows Saytzeff rule.
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Reactions with metal
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Organic chlorides, bromides and iodides reacts
with certain metals to give compounds containg
C-Metal compounds, known as organometalic
compounds
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Grignard reagents are highly reactive and react
with any source of proton to give hydrocarbons.
Even water, alcohols, amines are sufficient to
convert them to hydrocarbons
Wurtz reaction:
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HOME WORK
●
Why Aryl halides are extremely less reactive
towards nucleophilic substitution reaction ? How
chlorobenzene can be converted to phenol ?
●
Submit the answer in google
classroom
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Due date- 10th oct 11.59 pm
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Home work
●
Explain the electrophilic substitution of
haloarenes. Write down the (i)Halogenation,
(ii)Nitration, (iii) Sulphonation (iv) Friedal craft
reaction reactions of Chlorobenzene
Submit the answer in google
classroom
●
Due date- 10th oct 11.59 pm 18 / 20
Reactions with metal
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Wurtz-Fittig reaction: A mixture of alkyl halide
and aryl halide gives alkylarene when treated
with sodium in dry ether.
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Fittig reaction: Aryl halides when treated with
sodium dry ether, the aryl groups are joined
together.
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Thank you
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