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.
The “free-base” form of cocaine (C17H21NO4) and its protonated
hydrochloride form (C17H22ClNO4) are shown
below; the free-base form can be converted to the hydrochloride
form with one equivalent of HCl. For clarity, not
all the carbon and hydrogen atoms are shown; each vertex
represents a carbon atom with the appropriate number of
hydrogen atoms so that each carbon makes four bonds to
other atoms.
(a) One of these forms of cocaine is relatively water-soluble:
which form, the free base or the hydrochloride?
(b) One of these forms of cocaine is relatively insoluble in
water: which form, the free base or the hydrochloride?
(c) The free-base form of cocaine has a solubility of 1.00 g in
6.70 mL ethanol (CH3CH2OH). Calculate the molarity
of a saturated solution of the free-base form of cocaine in
ethanol.
(d) The hydrochloride form of cocaine has a solubility of
1.00 g in 0.400 mL water. Calculate the molarity of a saturated
solution of the hydrochloride form of cocaine in
water.
(e) How many mL of a concentrated 18.0 M HCl aqueous
solution would it take to convert 1.00 kilograms
(a “kilo”) of the free-base form of cocaine into its hydrochloride
form?
Trending now
This is a popular solution!
Step by step
Solved in 3 steps with 1 images
