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Asked: 2022-04-10T07:42:09+00:00 In:

Rank the following structures in order of decreasing electrophile strength.

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Rank the following structures in order of decreasing electrophile strength.

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Rank the following structures in order of decreasing electrophile strength.

♦ Relevant knowledge
Nucleophiles:

A compound or molecule is deemed as a nucleophile if it contains at minimum one electron pair that can be transferred to the compound that accepts it or an electron-deficient compounds. The nucleophile’s strength grows as the electron-releasing band around the nucleophilic nucleophilic atom expands.

 

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    Concepts and Reason

    a) Electrophile:

    The electrophilic atom in organic chemistry is typically a carbon atom that is bonded with electronegative atoms like nitrogen, oxygen, 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.

    b) 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.

    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.

    Answer:

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