Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic steps. Be sure to account for all bond-breaking and bond-making steps. :0: H HON N. Select to Add Arrows H Select to Add Arrows (CH3CH2)2NH2+ (CH3CH2)2NH (CH3CH2)2NH2+ (CH3CH2)2NH (CH3CH2)2NH2* (CH3CH2)2NH 0:0 H-N Select to Add Arrows (CH3 CH2)2NH2* (CH3CH2)2NH HO-N Select to Add Arrows
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.
![The diagram illustrates a mechanism involving the transformation of chemical structures in the presence of diethylamine (CH₃CH₂)₂NH and its protonated form (CH₃CH₂)₂NH₂⁺. The sequence includes a cyclic flow of possible reactions, where intermediates can be stabilized and transferred between different states.
1. **Initial Structures**:
- The top left and bottom left boxes contain a chemical compound with a benzene ring, and various substituents. Each structure includes a section labeled "Select to Add Arrows," indicating that there are potential electron movements or reaction pathways to explore.
2. **Reaction Arrows**:
- The arrows connecting these structures denote a reversible reaction between the compound and its interaction with diethylamine and its conjugate acid.
3. **Mechanism Steps**:
- At the top, the compound can transition between one depicted structure to another on the right through a step mediated by diethylamine. This transformation is indicated by arrow movement to the right.
- At the center, the reversible nature is shown again, highlighting the role of the protonated diethylamine in the backward reaction.
- Finally, at the bottom right, a transformation in the presence of diethylamine enables the compound to reach an end state, as depicted in the bottom right structure.
**Graphical Representation**:
- Each box contains chemical structures that indicate potential sites for reaction and electron movement.
- Chemical bonds and specific atoms are shown in standard chemical notation, with particular attention to nitrogen, oxygen, and hydrogen atoms due to their role in the reaction.
This diagram serves as an educational tool for exploring chemical reaction mechanisms and understanding the dynamic equilibrium between different chemical states in the presence of a basic amine and its conjugate acid.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ffee5a196-0e10-4c2e-9c7f-7471e7c61611%2F354a2e04-3eef-43c7-9060-e9759fbe2e61%2Fva5l7dt_processed.png&w=3840&q=75)
![### Electron Flow in Reaction Mechanisms
Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic steps.
Be sure to account for all bond-breaking and bond-making steps.
#### Diagrams
1. **Top Left Structure:**
- **Components:** This shows a benzene ring attached to a chain with an oxygen (O) and hydrogen (H) connected to a nitrogen (N) atom. There is a second nitrogen atom bonded to an ethyl group.
- **Label:** "Select to Add Arrows"
2. **Middle Structure:**
- **Components:** Represents the reaction pathway with two sets of arrows indicating forward and reverse reactions.
- **Label:** (CH₃CH₂)₂NH₂⁺ and (CH₃CH₂)₂NH
3. **Top Right Structure:**
- **Components:** Similar to the first structure with slightly different bonding, showing a positively charged nitrogen with electron pair interactions.
- **Label:** "Select to Add Arrows"
4. **Bottom Structures:**
- **Left and Right:** Represent the continuation of the reaction mechanism, showcasing similar components with small variations in bonding and labeling the forward (CH₃CH₂)₂NH₂⁺ and reverse (CH₃CH₂)₂NH reactions.
- **Label:** "Select to Add Arrows"
#### Notes:
- These structures depict the various stages in an electron-flow mechanism, emphasizing the role of curved arrows to show the movement of electron pairs.
- The arrows and chemical structures illustrate the equilibrium and dynamic nature of the reaction.
- Students should focus on identifying where electrons move during bond formation and cleavage.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ffee5a196-0e10-4c2e-9c7f-7471e7c61611%2F354a2e04-3eef-43c7-9060-e9759fbe2e61%2Fk3sellh_processed.png&w=3840&q=75)
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