Rank the following structures in order of decreasing electrophile strength.
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Question “Rank the following structures in order of decreasing electrophile strength.”
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Rank the following structures in order of decreasing electrophile strength.
Rank the following structures in order of decreasing electrophile strength.
Answer
General guidance
Concepts and Reason
Electrophile:
The electrophilic atom in organic chemistry is usually a carbon-atom that is bonded with electronegative atoms like oxygen, nitrogen, and fluorine. These kinds of molecules can experience separation of charges (polarization). Polarization results in the carbon atom having a partial positive charge, while the electronegative has a partial negative charge. The molecule is called an electrophile.
Resonance:
A conjugated molecule has a lone/pi bond pair of electrons that moves along sigma bonds within the molecule. This can lead to different arrangements for electrons in the same molecules. It is known as a resonance.
Fundamentals
Inductive effect:
Inductive effects are caused by the introduction of electronegative atoms (nitrogen or oxygen) which pulls electrons from bond pairs through sigma bonds. This makes the carbon in a C=O bonded more electrophilic. Take, for example:
Alkyl groups can be introduced to cause a positive inductive impact, which is the donation electrons through sigma bond. This makes carbon in a C=O bonds less electrophilic. Take, for example:
Step-by-step
Step 1 from 2
Separation of partial charges:
Resonance:
Common mistakes
The oxygen atom pulls electrons away from the carbonyl functional group. This makes the carbon more electrophilic because it is more electronegative than carbon.
Due to its resonance structures, the carbon atom of a protonated group receives a positive charge.
Don’t confuse partial positive/negative charges.
is a partial positive charge on carbon atom.
is a partial negative charge on an oxygen atom.
Sort the structures in the order of their electrophilic strength.
Step 2 from 2
Descending order in electrophilic strength
Because the carbon atom is full of positive charge, the protonated carbonyl groups is the most electrophilic. It is therefore the most electrophilic group in order of strength.
Fluorine substituted carbonyls have a higher electrophilic value because of the negative inductive effect. It is therefore ranked second in the descending order for electrophilic strength.
Because of the positive inductive effect, alkyl substituted carbonyls have a lower electrophilic nature. These molecules are ranked according to increasing carbon chain length and decreasing electrophilic strength.
Use the concepts of resonance or inductive effect to help you rank the molecules.
Answer
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