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Opposites Attract and Like Repel.: Inductive Effect Resonance Effect

The document discusses several key factors that influence chemical reactions: 1. The energetics of reactions, whether they release or require energy in the form of activation energy. 2. Electronic effects, including inductive effects of electronegativity differences between atoms and resonance effects of electron movement. Electrophiles and nucleophiles are attracted to each other. 3. Steric effects of atomic crowding causing repulsions that can hinder reactions and conformational changes. 4. Stereoelectronic effects where orbital alignment impacts reactivity. 5. Solvent effects, as most reactions occur in solution and the solvent can strongly influence the reaction path.

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Awais Arshad
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693 views

Opposites Attract and Like Repel.: Inductive Effect Resonance Effect

The document discusses several key factors that influence chemical reactions: 1. The energetics of reactions, whether they release or require energy in the form of activation energy. 2. Electronic effects, including inductive effects of electronegativity differences between atoms and resonance effects of electron movement. Electrophiles and nucleophiles are attracted to each other. 3. Steric effects of atomic crowding causing repulsions that can hinder reactions and conformational changes. 4. Stereoelectronic effects where orbital alignment impacts reactivity. 5. Solvent effects, as most reactions occur in solution and the solvent can strongly influence the reaction path.

Uploaded by

Awais Arshad
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PPTX, PDF, TXT or read online on Scribd
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Factors that Influence Reactions

It is helpful to identify some general features of a reaction that have a significant influence on its facility. Some of the most important of these are:

A. Energetics: The potential energy of a reacting system changes as the reaction progresses. The
overall change may be exothermic ( energy is released ) or endothermic ( energy must be added ),
and there is usually an activation energy requirement as well.

B. Electronic Effects: The distribution of electrons at sites of reaction (functional groups) is a


particularly important factor. Electron deficient species or groups, which may or may not be positively
charged, are attracted to electron rich species or groups, which may or may not be negatively
charged. We refer to these species as electrophiles & nucleophiles respectively. In general,
opposites attract and like repel.
The charge distribution in a molecule is usually discussed with respect to two interacting effects: An
inductive effect, which is a function of the electronegativity differences that exist between atoms (and
groups); and a resonance effect, in which electrons move in a discontinuous fashion between parts
of a molecule.

C. Steric Effects: Atoms occupy space. When they are crowded together, van der Waals repulsions
produce an unfavorable steric hindrance. Steric hindrance may influence conformational equilibria,
as well as destabilizing transition states of reactions.

D. Stereoelectronic Effects: In many reactions atomic or molecular orbitals interact in a manner that
has an optimal configurational or geometrical alignment. Departure from this alignment inhibits the
reaction.

E. Solvent Effects: Most reactions are conducted in solution, not in a gaseous state. The solvent
selected for a given reaction may exert a strong influence on its course. Remember, solvents are
chemicals, and most undergo chemical reaction under the right conditions.
Inductive effect
The inductive effect is a permanent state
of polarization. The electron density in a
bond between two unlike atoms is not
uniform. The electron density is more
dense toward the more electronegative of
the two atoms. The inductive effect is a
distance-dependent phenomenon.
c-x
-I effect:
The -I effect is seen around a more
electronegative atom or group, and electron
density is higher there than elsewhere in the
molecule. Electron-withdrawing groups include
halogen, nitro (), cyano (), carboxy (), ester (),
and aryloxy ().
+I effect:
The +I effect is observed among the less
electronegative atoms of the molecule by
electron releasing(or electron donating) groups.
The alkyl groups are usually considered electron
releasing (or electron donating) groups.
Factors that Determine Acid Strength—Inductive Effects

• An inductive effect is the pull of electron density through  bonds caused by


electronegativity differ-ences between atoms.
• In the example below, when we compare the acidities of ethanol and 2,2,2-
trifluoroethanol, we note that the latter is more acidic than the former.

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• The reason for the increased acidity of 2,2,2-trifluoroethanol is that the three
electronegative fluorine atoms stabilize the negatively charged conjugate base.

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• When electron density is pulled away from the negative charge through 
bonds by very electronegative atoms, it is referred to as an electron
withdrawing inductive effect.
• More electronegative atoms stabilize regions of high electron density by
an electron withdrawing inductive effect.
• The more electronegative the atom and the closer it is to the site of the
negative charge, the greater the effect.
• The acidity of H—A increases with the presence of electron withdrawing
groups in A.

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