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.
Can you show the mechanism and the products for those problems especially the ones that I put circle on
![Hal L
osengtion
Ditaption.
Sul
suke
hghos
Alkyle
T
gi.
Aey
Iphon
Br₂/FeBr3
Cl₂/AICI
HNO3/H₂SO
H₂SO4
CH3CH₂Cl
AICI 3
O
11
CH3CCI
AICI 3
D
1. Mg, Et₂0
2. CO2, H3O+
1. Mg, Et₂0
2. CO₂, H3O
Br
CI
Zn(Hg)
HCI,A
(reduction)
1. Sn/HCI
−NO₂ 20H-
SO3H
KMnO4/H₂SO4
(oxidation)
CH₂CH3
CCH3
CH₂CH3
COOH
1. NaOH, -300 °C
2. H3O+
CH COCI, H3O+
KMnO4
H₂SO4
NBS/A
ROOR
1. NaBH₁
2. H30
KMnO4,
H₂SO4
O
11
NHCCH3
E
COOH
1.NaNO2
2.HCI, 0°C
NH₂
ОН
Br
OH SN-2
Î
N
ОН
CHCH3
ZEZ
N
HO
CHCHA E-2
Diazonium
lon
Acetylption
H₂SO4
1 E-1
A
BH3**, THF
Stills Reduction
CH=CH₂
1. BH3
2. HO, H₂O₂
Reactions of Diazonium
lon are given on the
previous page
HBr
peroxide
ОН
(10 alcohol)
CH₂CH₂OH
ydnu boration
CH₂CH₂Br
USE
Revie
SCA
BH3**= In place of BH3, 9-BBN (N-
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