Questions: 1) Explain the molecular basis of the reaction of bromine water with phenol. 2) What is/are the difference/s in the reactivity of primary, secondary, and tertiary alcohol with sodium metal and concentrated HCI? 3) Explain the molecular basis in Millon's test for phenols.
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.
![TESTS FOR ALCOHOLS AND PHENOLS
Materials:
Test tube - 12
Test tube rack
Test tube holder
Graduated cylinder (100mL) – 1
Alcohol lamp
Crucible tong
Chemicals:
Ethanol
Isopropyl alcohol
Tertiary butyl alcohol
Ferric chloride solution
Sodium metal
Lucas' reagent
Concentrated sulfuric acid
Potassium dichromate solution
Phenol
Millon's reagent
Bromine water
Procedure:
A) Tests for alcohols
1) Sodium metal:
Place 1 ml of each of the following: ethanol, isopropyl alcohol, and tertiary butyl alcohol in
separate test tubes. Add a small piece of sodium metal to the different alcohols. Take note
of the difference in the release of hydrogen gas.
2) Lucas' test:
Place 1 ml of each of the following: ethanol, isopropyl alcohol, and tertiary butyl alcohol in
separate test tubes. Add 1 ml of hydrochloric acid and 1 g of anhydrous zinc chloride to the
different alcohols. Take note of the difference in the formation of cloudy solution.
3) Oxidation:
Place 1 ml of each of the following: ethanol, isopropyl alcohol, and tertiary butyl alcohol in
separate test tubes. Add 10 drops of potassium dichromate and 5 drops of concentrated
sulfuric acid to the different alcohols. Take note of the odor and color of the products.
B) Tests for phenols
1) Bromine water:
Add 1 ml of bromine water to phenol and take note of the color of the precipitate.
2) Ferric chloride test:
Add 5 drops of ferric chloride solution to phenol. Take note of the color formed.
3) Millon's test:
Add 5 drops of Millon's regent to phenol. Take note of the color formed.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fbe790e90-3d8a-40f4-8d4b-f4cb26815222%2Ff52567d9-50df-4fe5-a643-c55a95f264b4%2F3x4j8b_processed.jpeg&w=3840&q=75)
![Questions:
1) Explain the molecular basis of the reaction of bromine water with phenol.
2) What is/are the difference/s in the reactivity of primary, secondary, and tertiary alcohol with
sodium metal and concentrated HCI?
3) Explain the molecular basis in Millon's test for phenols.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fbe790e90-3d8a-40f4-8d4b-f4cb26815222%2Ff52567d9-50df-4fe5-a643-c55a95f264b4%2F4havx2s_processed.jpeg&w=3840&q=75)
![](/static/compass_v2/shared-icons/check-mark.png)
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)