1st attempt 1. Nucleophilic addition involving H₂CO CI 2. Nucleophile elimination Be sure to include all lone pair electrons and nonzero formal charges. Step 1 Step 2 Draw H3CO, and then add curved arrow notation showing nucleophilic addition.
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.
Draw the curved arrow notation and products for the each elementary step described by the sequence shown here.
Note that the products of the first step should be used as the reactants in the second step, and remember to click on each box to see step-specific instructions.
#### Step 1: Nucleophilic Addition
- Illustrate the interaction between the methoxide ion (H₃CO⁻) and the carbonyl group (C=O) on the cyclic compound.
- Highlight the nucleophilic attack on the electrophilic carbon of the carbonyl group.
#### Step 2: Nucleophile Elimination
- Show the elimination process where the leaving group (chlorine, Cl) departs from the compound.
- Ensure the final product of the reaction is depicted with correct electron placement and formal charges.
#### Notes:
- **Be sure to clearly distinguish each step in your diagrams.**
- **Include all necessary electrons and charges for a thorough representation.**
This process illustrates the common organic chemistry reaction mechanisms of nucleophilic addition followed by elimination, integral to understanding advanced synthetic pathways.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fd3a4fb95-1521-4ff9-a079-f7c4aa007149%2F825849a2-91df-4ac7-8b52-5f3ea955e19a%2Fvvt05u_processed.png&w=3840&q=75)
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