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Chemical Reactions, Stereochemical Aspects

This document discusses stereochemical aspects of nucleophilic substitution reactions. It begins by stating that SN2 reactions proceed with complete stereochemical inversion, while SN1 reactions proceed with racemization. It then provides background on several key stereochemical principles, including optical activity, chirality, retention, inversion, and racemization. Examples of chiral molecules and enantiomers are given. The document also discusses elimination reactions, reactions of organic halides with metals like Grignard reagents, and provides homework questions.

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Kalpa Dihingia
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2K views20 pages

Chemical Reactions, Stereochemical Aspects

This document discusses stereochemical aspects of nucleophilic substitution reactions. It begins by stating that SN2 reactions proceed with complete stereochemical inversion, while SN1 reactions proceed with racemization. It then provides background on several key stereochemical principles, including optical activity, chirality, retention, inversion, and racemization. Examples of chiral molecules and enantiomers are given. The document also discusses elimination reactions, reactions of organic halides with metals like Grignard reagents, and provides homework questions.

Uploaded by

Kalpa Dihingia
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Chemical Reactions,

Stereochemical aspects
Lecture by Kalpajyoti Dihingia
Department of Chemistry
DHSK college, Dibrugarh
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Stereochemical aspects of
nucleophilic substitution reaction

●
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
●
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

●
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.

4 / 20
Molecular asymmetry,
chirality and enantiomers
●
The difference in optical activity is associated
with 3-D arrangements of atoms( configurations)
●
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

6 / 20
Non-superimposable
objects

Note:
Non-superimposable
- chiral, chirality

7 / 20
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
(+_)

11 / 20
Retention of configuration
●
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

13 / 20
Elimination reaction

●
There is elimination of H from ¯ carbon atom.
Therefore it is often called ¯ elimination.
●
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
●
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
●
Due date- 10th oct 11.59 pm

17 / 20
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
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Reactions with metal
●
Wurtz-Fittig reaction: A mixture of alkyl halide
and aryl halide gives alkylarene when treated
with sodium in dry ether.

●
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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