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.
Please provide a mechanism with curved arrows for this reaction.
![Experiment 8: Fischer Esterification (Data Sheet)
Running the reaction
1.20 mL of isopentyl alcohol and 1.70 mL of glacial acetic acid were placed in a 5 mL
conical vial
Three drops of concentrated sulfuric acid were added
An air condenser (cooled with a wet paper towel) was added and the mixture was gently
refluxed for 60 minutes
Upon cooling, two layers form: the smaller layer making the bottom layer
Product isolation
After the removal of the air condenser, 1 mL of 5 % sodium bicarbonate solution was
added; the mixture was gently mixed leading to foaming (CO2 formation); the bottom layer
was removed
Two more extractions with 1 mL of 5 % sodium bicarbonate solution were performed, the
last one barely leading to any bubble formation
The organic layer was transferred to a clean test tube and dried over three microspatulas of
anhydrous sodium sulfate
The dry organic layer was transferred to a 3 mL conical vial; a Hickman head is attached
and a thermometer placed inside the Hickman head
The crude was distilled until only two drops remained in the vial
Product characterization
1.05 g of the product
B.p.: 138.5-141.5 °C
Refractive index: np18= 1.3980](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F21b4e0fd-2deb-4010-bcaa-5e17a99ed39c%2Fc07161c2-78d3-4999-a819-88d776aed7dc%2Fljcinsc_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 3 steps with 1 images
![Blurred answer](/static/compass_v2/solution-images/blurred-answer.jpg)
![Chemical Principles in the Laboratory](https://www.bartleby.com/isbn_cover_images/9781305264434/9781305264434_smallCoverImage.gif)
![Organic Chemistry: A Guided Inquiry](https://www.bartleby.com/isbn_cover_images/9780618974122/9780618974122_smallCoverImage.gif)
![Introduction to General, Organic and Biochemistry](https://www.bartleby.com/isbn_cover_images/9781285869759/9781285869759_smallCoverImage.gif)
![Chemical Principles in the Laboratory](https://www.bartleby.com/isbn_cover_images/9781305264434/9781305264434_smallCoverImage.gif)
![Organic Chemistry: A Guided Inquiry](https://www.bartleby.com/isbn_cover_images/9780618974122/9780618974122_smallCoverImage.gif)
![Introduction to General, Organic and Biochemistry](https://www.bartleby.com/isbn_cover_images/9781285869759/9781285869759_smallCoverImage.gif)
![EBK A SMALL SCALE APPROACH TO ORGANIC L](https://www.bartleby.com/isbn_cover_images/9781305446021/9781305446021_smallCoverImage.jpg)
![Macroscale and Microscale Organic Experiments](https://www.bartleby.com/isbn_cover_images/9781305577190/9781305577190_smallCoverImage.gif)
![Introductory Chemistry: A Foundation](https://www.bartleby.com/isbn_cover_images/9781337399425/9781337399425_smallCoverImage.gif)