Curved arrows are used to illustrate the flow of electrons. Follow the curved arrows and draw the product of the E2 reaction shown below. Include all lone pairs. Ignore byproducts. :Br: H CH3OH heat -CH3 Q
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 the E2 Reaction Mechanism**
In this exercise, we explore the elimination reaction mechanism (E2) depicted in the diagram above. **Curved arrows** are used to illustrate the movement of electrons during the reaction. Follow these arrows to understand the changes taking place in the molecule. The goal is to identify the product formed by the E2 reaction and note all lone pairs. Byproducts should be ignored.
### Diagram Explanation:
1. **Chemical Structure:**
- The starting molecule is a bromoalkane. The carbon chain is bonded to a bromine atom (\(\text{Br}\)) with two lone pairs, and adjacent to it is a hydrogen atom (\(\text{H}\)).
2. **Curved Arrows:**
- **First Arrow:** Indicates the removal of the bromine atom as a leaving group, taking its electron pair with it.
- **Second Arrow:** Shows the abstraction of a hydrogen (\(\text{H}\)) atom by the negatively charged methoxide ion (\(\text{O}^\ominus\)—\(\text{CH}_3\)).
- **Third Arrow:** Demonstrates the formation of a double bond between the two carbon atoms as the electrons from the C-H bond shift into the space between them.
3. **Reactants and Conditions:**
- The reaction occurs in the presence of methanol (\(\text{CH}_3\text{OH}\)) and heat, facilitating the elimination process.
### Objective:
By carefully analyzing and executing the E2 mechanism, draw the resulting alkene by forming a double bond and including all relevant lone pairs on atoms. This exercise will enhance your understanding of electron movement and bond formation in chemical reactions.
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**Note:** The E2 mechanism usually proceeds in a single, concerted step, where the base abstracts a proton, simultaneous to the leaving group departure, resulting in the formation of a double bond.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F9b60de5f-8fb0-4e3b-8258-2de6c1a93a8c%2Ff916b55a-78d2-4571-9db9-1639ee51e339%2Fqdm31w8_processed.png&w=3840&q=75)
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