Shown on the left is a cationic intermediate for the electrophilic addition of chlorine to the para position phenol. Draw the resonance stucture that is the major contributor. Include all nonbonding electrons. click to edit H.
Basics in Organic Reactions Mechanisms
In organic chemistry, the mechanism of an organic reaction is defined as a complete step-by-step explanation of how a reaction of organic compounds happens. A completely detailed mechanism would relate the first structure of the reactants with the last structure of the products and would represent changes in structure and energy all through the reaction step.
Heterolytic Bond Breaking
Heterolytic bond breaking is also known as heterolysis or heterolytic fission or ionic fission. It is defined as breaking of a covalent bond between two different atoms in which one atom gains both of the shared pair of electrons. The atom that gains both electrons is more electronegative than the other atom in covalent bond. The energy needed for heterolytic fission is called as heterolytic bond dissociation energy.
Polar Aprotic Solvent
Solvents that are chemically polar in nature and are not capable of hydrogen bonding (implying that a hydrogen atom directly linked with an electronegative atom is not found) are referred to as polar aprotic solvents. Some commonly used polar aprotic solvents are acetone, DMF, acetonitrile, DMSO, etc.
Oxygen Nucleophiles
Oxygen being an electron rich species with a lone pair electron, can act as a good nucleophile. Typically, oxygen nucleophiles can be found in these compounds- water, hydroxides and alcohols.
Carbon Nucleophiles
We are aware that carbon belongs to group IV and hence does not possess any lone pair of electrons. Implying that neutral carbon is not a nucleophile then how is carbon going to be nucleophilic? The answer to this is that when a carbon atom is attached to a metal (can be seen in the case of organometallic compounds), the metal atom develops a partial positive charge and carbon develops a partial negative charge, hence making carbon nucleophilic.
Shown on the left is a cationic intermediate for the electrophilic addition of chlorine to the para position of phenol. Draw the resonance stucture that is the major contributor. Include all nonbonding electrons.
![### Resonance Structures in Electrophilic Aromatic Substitution
#### Objective
Shown on the left is a cationic intermediate for the electrophilic addition of chlorine to the para position of phenol. Draw the resonance structure that is the major contributor. Include all nonbonding electrons.
#### Graphical Content
- A benzene ring structure is illustrated with:
- A hydroxyl group (-OH) attached to the first carbon.
- A chlorine atom (Cl) attached to the para (fourth) carbon, with three lone pairs of electrons.
- A positive charge (+) is shown on the benzene ring, representing a cationic intermediate.
- Nonbonding and lone pair electrons are indicated for both oxygen and chlorine atoms.
#### Step-by-Step Solution
- Identify the para substitution pattern on the benzene ring:
- The chlorine atom is directly across from the hydroxyl group (para position).
- Understand the positive charge distribution and electron delocalization in aromatic rings:
- The positive charge on the benzene ring creates a resonance structure.
- Draw all resonance structures considering the delocalization of the positive charge and electron movement:
- Utilize curved arrows to show movement of electrons between bonds.
- Include lone pairs and properly place them on atoms where they naturally reside.
#### Diagrams
- Use the provided grid on the right to draw the resonance structures. Ensure that:
- All nonbonding electrons are clearly marked on oxygen and chlorine atoms.
- Curved arrows correctly show the movement of electrons that result in different resonance forms.
- Drawing the major resonance contributor should account for the stabilization of the aromatic ring due to electron delocalization.
Use the above steps and diagram guidelines to represent the resonance structures effectively.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F37e1710d-5d92-4416-9037-10beff7be39e%2Fe0c7c95c-c02d-4859-89d7-0d82b15f946a%2Famk01ya.png&w=3840&q=75)
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