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.
Phenylamine is an
causes the Fe+2 in hemoglobin to become oxidized into Fe+3, resulting in the formation of methemoglobin which
cannot bind to or transport oxygen. Phenylamine is soluble in water and acts as a weak base.
C6H5NH2 (aq) + H2O (ℓ) ⇋ C6H5NH3+ (aq) + OH- (aq)
a. When you measure the concentrations of the ionized substances you find them to be:
[C6H5NH2] = 0.234 mol/L [C6H5NH3+] = 2.8 x 10-5 mol/L [OH-]= 2.8 x 10-5 mol/L
If the Kb is 4.27 x 10-10, is the reaction at equilibrium? If not, which direction does it need to move (right
or left) to reach equilibrium? Explain.
b. At equilibrium the concentrations of the ionized substances are:
[C6H5NH2] = 0.0537 mol/L [C6H5NH3+] = 4.79 x 10-6 mol/L [OH-]= 4.79 x 10-6 mol/L
If this reaction is taking place in a 2.0L container, and 1.5 moles of phenylamine were added to the
reaction, what will the new concentrations of the three ionic species be when equilibrium is reestablished?
![Phenylamine is an aromatic amine that is used in the manufacture of dyes. When absorbed through the skin it
causes the Fe*² in hemoglobin to become oxidized into Fe+3, resulting in the formation of methemoglobin which
cannot bind to or transport oxygen. Phenylamine is soluble in water and acts as a weak base.
a.
C6H5NH₂ (aq) + H₂O (l) C6H5NH3+ (aq) + OH- (aq)
When you measure the concentrations of the ionized substances you find them to be:
[C6H5NH₂] = 0.234 mol/L
[C6H5NH₂*] = 2.8 x 10³ mol/L
[OH-]= 2.8 x 10³ mol/L
If the K, is 4.27 x 10:¹0, is the reaction at equilibrium? If not, which direction does it need to move (right
or left) to reach equilibrium? Explain.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F611a242a-940a-481d-9161-5e558805e861%2F36e57494-08df-439f-91f2-4650eccfe94e%2Fbf5wr1k_processed.png&w=3840&q=75)
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a.
At equilibrium the concentrations of the ionized substances are:
[C6H5NH₂] = 0.0537 mol/L [C6H5NH3*] =4.79 x 10 mol/L [OH]=4.79 x 10¹ mol/L
If this reaction is taking place in a 2.0L container, and 1.5 moles of phenylamine were added to the
reaction, what will the new concentrations of the three ionic species be when equilibrium is re-
established?
CoHsNHz (aq)
H₂O(l)
C6H5NH3+ (aq)
OH- (aq)](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F611a242a-940a-481d-9161-5e558805e861%2F36e57494-08df-439f-91f2-4650eccfe94e%2Fwnhmo0m_processed.png&w=3840&q=75)
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