Based on the results of the solubility tests and chemical tests, what is the most probable structure of C6H5C3H5O? Draw your answer in the box You may draw the compound usingline-bond formula OR Lewis structure. Problem statement: You were tasked to propose a structure for a compound with a chemical formula of C6H5C3H5O. In the laboratory, the compound appears as a clear, colorless liquid.
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.
Answer this question:
Based on the results of the solubility tests and chemical tests, what is the most probable structure of C6H5C3H5O? Draw your answer in the box You may draw the compound usingline-bond formula OR Lewis structure.
Problem statement:
You were tasked to propose a structure for a compound with a chemical formula of C6H5C3H5O. In the laboratory, the compound appears as a clear, colorless liquid.
See table 1, for the results of solubility tests for C6H5C3H5O.
Table 1. Results of the solubility tests for C6H5C3H5O.
|
SOLUBILITY TEST |
OBSERVATIONS |
+(soluble/miscible)/ - (insoluble) |
|
distilled water |
two layers of liquid |
- |
|
10% NaHCO3 |
two layers of liquid |
- |
|
10% NaOH |
two layers of liquid |
- |
|
10% HCl |
two layers of liquid |
- |
|
concentrated H2SO4 |
pinkish solution |
+ |
Based on the results of the solubility tests, the compound can be grouped in VI, which is insoluble in water, 10% NaOH and 10% HCl but soluble in concentrated H2SO4.
If the compound is water-insoluble but soluble in concentrated H2SO4, it is most probably an alcohol,
The
|
CHEMICAL TEST |
OBSERVATIONS |
+(compound tested positive for the otherwise (-) |
|
Molisch test |
turbid colorless solution |
- |
|
2,4-DNP test |
formation of orange-yellow precipitates |
+ |
|
Tollen’s test |
turbid colorless solution |
- |
|
Ninhydrin test |
clear pale-yellow solution |
- |
|
iodoform test |
clear pale-yellow solution |
+ |
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