Curved arrows are used to illustrate the flow of electrons. Follow the curved arrows and draw the missing intermediates and product of this hydrohalogenation reaction. Include all lone pairs and charges as appropriate. Select to Draw D H3O+ 1,2-hydride shift 1,2-alkyl shift Select to Draw 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.
![**Title: Understanding Electrophilic Addition and Rearrangements in Hydrohalogenation Reactions**
**Curved arrows are used to illustrate the flow of electrons. Follow the curved arrows and draw the missing intermediates and product of this hydrohalogenation reaction. Include all lone pairs and charges as appropriate.**
**Reaction Steps and Diagrams:**
1. **Initial Structure and Electron Flow:**
- The starting molecule is a cyclohexene with an additional double bond extending to an adjacent carbon, depicted with a pair of curved arrows indicating electron movement towards a positively charged hydronium ion (\(H_3O^+\)).
2. **Formation of Carbocation Intermediate:**
- After the initial reaction with \(H_3O^+\), the intermediate structure forms a carbocation. This is shown by a cyclohexyl group with a positive charge on a carbon atom and a hydrogen atom added.
3. **Rearrangements:**
- **1,2-Alkyl Shift:**
- The carbocation undergoes a 1,2-alkyl shift, signifying the movement of an alkyl group from one carbon to the adjacent positively charged carbon, rearranging the structure for stability.
- **1,2-Hydride Shift:**
- Following the alkyl shift, a 1,2-hydride shift occurs, demonstrating the transfer of a hydride ion (H-) to another adjacent carbon, further stabilizing the carbocation.
4. **Final Product Formation:**
- The presence of water (\(H_2O\)) ultimately restores neutrality by adding to the carbocation, leading to the formation of the final product.
The diagram showcases placeholders marked "Select to Draw" for learners to fill in the missing intermediate and final structures, indicating active participation in understanding the reaction mechanism.
**Conclusion:**
This exercise enables the understanding of electron flow during hydrohalogenation, the concept of carbocation stability, and rearrangements like alkyl and hydride shifts, crucial in organic reaction mechanisms.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F1ba2f8b0-0e44-4073-8850-ce5b48deecdf%2F6ea271ca-83fd-4eed-bf61-6ebe491aeefb%2Flx7dfsd_processed.jpeg&w=3840&q=75)
![The image displays a schematic diagram with four blank boxes labeled "Select to Draw," each surrounded by dashed lines. These boxes represent stages in a chemical reaction or pathway. The diagram includes arrows indicating the direction of shifts and reactions:
1. **1,2-Alkyl Shift**: An arrow points downward into the second box from the top right, indicating that a 1,2-alkyl shift occurs between the first and second boxes.
2. **1,2-Hydride Shift**: Another arrow connects the second box back to the first box on the top left, showing a 1,2-hydride shift.
3. **H₂O**: A vertical arrow pointing downward from the top left box to a lower left box, and a horizontal arrow pointing from the lower left box to the lower right box, both labeled with "H₂O," suggesting the involvement of water in these transitions.
These shifts and reactions are fundamental concepts in organic chemistry, related to the rearrangement of carbocations, which often enhance stability in molecular transformations. The site appears to represent a platform where users can interactively draw or predict the resulting structures at each stage.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F1ba2f8b0-0e44-4073-8850-ce5b48deecdf%2F6ea271ca-83fd-4eed-bf61-6ebe491aeefb%2Fctprpzq_processed.jpeg&w=3840&q=75)
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