Without rotating the bond, draw a proper Newman structure of the following molecule, looking down the bond in the direction of the arrow. OH Br [Select] <>
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.
![### Analyzing and Drawing Newman Projections
#### Problem Statement
Without rotating the bond, draw a proper Newman structure of the following molecule, looking down the bond in the direction of the arrow:
![Molecular Diagram]()
- The molecule has an -OH (hydroxyl group) attached to the first carbon and a -Br (bromine atom) attached to the second carbon.
#### Diagram Explanation
Here is the molecular structure with an arrow indicating the bond to be analyzed:
- The hydroxyl group (-OH) is on the carbon that the arrow points FROM.
- The bromine atom (-Br) is on the carbon that the arrow points TOWARD.
#### Instructions
Select the appropriate Newman projections from the drop-down menus for both the front and rear carbon atoms from the viewpoint indicated.
#### Newman Projection Diagram
Below is a blank Newman projection circle where you will place the substituents in the correct positions:
![Blank Newman Projection Circle]()
### Drop-Down Options
For various positions on the Newman projection, attribute the correct groups without rotating the bond:
1. Select the front carbon substituents:
- [ Select ]
2. Select the rear carbon substituents:
- [ Select ]
#### Final Tips
To accurately determine the correct Newman projection structure:
- Visualize the molecule's substituents from the arrow's perspective.
- Ensure that you account for the three-dimensional spatial arrangements, keeping in mind the consistency of your view with the bond direction.
Provide correct placement for substituents such as -OH, -Br, and any remaining hydrogen atoms. This practice is fundamental in understanding steric interactions and conformational analysis in organic chemistry.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F14c0e5a1-d742-4e41-8d41-3d55fde4a1b7%2Fd69cab76-7315-4be2-a764-0164cfd4a0ad%2F86xzawa_processed.jpeg&w=3840&q=75)
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