Intro To Organic Reactions CHM457
Intro To Organic Reactions CHM457
Intro To Organic Reactions CHM457
Introduction to
Organic Reaction
Reactions of the
Organic Compounds
H H
H C H + I2 H C I + HI
H H
methane iodomethane
Elimination Reaction
• Two or more atoms or carbons are
removed from a molecule and the product
form a multiple bond.
H H H H
H2SO4 + HBr
H C C Br C C
H H H H
Bromoethane ethene
Elimination Reaction: Formation of C=C
H Br OH- SO3H+
H2SO4 H C C H
H C C H
H H
H H
ethene
Bromoethane
1) The nucleophile (normally a strong base) + HBr
removes one atom (usually a proton, H+)
2) group on the adjacent carbon leaves
(the leaving group) and double bond is
formed between two adjacent carbon.
Addition Reaction
• Two reactants are combined together to
form a single product.
C C + HBr H C C Br
H H H H
ethene Bromoethane
11
Bond Breaking–Intermediates
12
Bond Forming
• Bond formation occurs in two different ways.
• Two radicals can each donate one electron to form a two-electron
bond.
• Two ions with unlike charges can come together, with the
negatively charged ion donating both electrons to form the
resulting two-electron bond.
• Bond formation always releases energy.
13
Electrophiles (electron-loving)
• A reagent which attacks a negatively
charged carbon atom (carbanion) by
accepting an electron pair.
+
X+ halonium ion C carbocation
H+ proton
H+ + H2O H3O+
from H2SO4 base conjugate
acid
H2SO4 HSO4- + H+
acid conjugate
base
Lewis Acids and Bases
• Lewis Acid: electron pair acceptor
• Lewis Base: electron pair donor
• Curved arrows show movement of electrons
to form and break bonds
The Use of Curved Arrows in Reactions
- +
[CH3COO ] [H3O ]
Kc =
[CH3COOH] [H2O]
HA + H2O H3O+ + A-
pKa = -log Ka
• The pKa for acetic acid is 4.75.
• There is an inverse relationship between
the magnitude of the pKa and the strength
of acid. The smaller the value of pKa, the
stronger the acid.
pKb = -log Kb
Most stable
Strong acid
Strong base
• The hybrids are defined by the p to s ratio of the contributing orbitals.
• Thus, an spm hybrid is composed of m+1 parts: one part of s and m parts of p.
• For example, an sp3 hybrid has ¼ (25%) of s and ¾ (75%) of p.
• This fraction is called an s (or p) character of the orbital.
• Thus, an sp3 hybrid has 25% s character.