The instructor said he was skipping a "cleanup step" where I circled in red, and went directly to the product of the reaction. Can someone draw the missing mechanism so I can better understand?
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.
I was watching a video. The instructor said he was skipping a "cleanup step" where I circled in red, and went directly to the product of the reaction. Can someone draw the missing mechanism so I can better understand?
![**Carboxylic Acids - Addition-Elimination Reaction**
This diagram illustrates the mechanism of an addition-elimination reaction involving carboxylic acids.
1. **Starting Materials:**
- A hydroxyl group (\(-OH\)) on a carboxylic acid, represented by the first structure with a carbonyl group (\(C=O\)).
- Methanol (\(CH_3OH\)) and a proton (\(H\)) participate as reactants.
2. **Reaction Mechanism:**
- **First Step:** The hydroxyl group acts as a nucleophile, attacking the carbon of the carbonyl group. This is indicated by a curved arrow pointing from the oxygen of the hydroxyl group to the carbon of the carbonyl group.
- **Intermediate Formation:** The intermediate with a positively charged oxygen is represented. A proton (\(+\)H) is lost in this step.
- **Methanol Attack:** Simultaneously, another curly arrow represents attack by methanol (\(CH_3OH\)) forming an ester linkage. Water (\(H_2O\)) is a byproduct.
- **Product Formation:** The final product is shown in a separate box, depicting an ester with the formula \(\text{OCH}_3\).
3. **Red Encircled Section:**
- This section details more about the attachment of \(CH_3OH\). The curly arrow shows proton transfer to form an ester while removing the water molecule.
This illustration explains how carboxylic acids undergo nucleophilic substitution to form esters, highlighting critical structural transformations during the reaction.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F7162f5a4-a0e5-4bd0-aafa-d48500254236%2Fc30a3a36-81d8-4ca4-9e8c-43c6db13a2c5%2Fn6b4hle_processed.png&w=3840&q=75)
![](/static/compass_v2/shared-icons/check-mark.png)
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 1 images
![Blurred answer](/static/compass_v2/solution-images/blurred-answer.jpg)
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
![Principles of Instrumental Analysis](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
![Principles of Instrumental Analysis](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9780078021558/9780078021558_smallCoverImage.gif)
![Chemistry: Principles and Reactions](https://www.bartleby.com/isbn_cover_images/9781305079373/9781305079373_smallCoverImage.gif)
![Elementary Principles of Chemical Processes, Bind…](https://www.bartleby.com/isbn_cover_images/9781118431221/9781118431221_smallCoverImage.gif)