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McMurry
http://www.cengage.com/chemistry/mcmurry
Chapter 1
Structure and Bonding
Organic Chemistry
Scientific advances in medicine and biology require an understanding of
organic chemistry
Organic and Biological Chemistry in Modern Medicine
Coronary artery disease (CAD) is directly correlated with blood
cholesterol levels
75% of blood cholesterol (1000 mg each day) is biosynthesized
Drugs known as Statins reduce the risk of CAD by lowering blood
cholesterol levels
3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) to mevalonate
conversion
Crucial step in biosynthesis of cholesterol
Atorvastatin (Lipitor) inactivates enzyme that catalyzes HMG-CoA to
mevalonate conversion
Organic Chemistry
Carbon
Organic chemistry
All organic compounds contain the element carbon
4A element
Shares four electrons
Forms four strong covalent bonds
Bonds to other carbons to create chains and rings
Not all carbon compounds are derived from living
organisms
Over 99% of 37 million known compounds contain
carbon
Nucleus
Positively charged
Made up of protons (positively charged) and neutrons (neutral)
Small (10-14 to 10-15 m in diameter)
Contains essentially all the mass of the atom
Electron cloud
Negatively charged electrons in cloud around nucleus
Atomic diameter is about 2 Angstroms ()
-10 m = 100 pm ; 1 pm = 10-12 m
1 = 10
Atomic diameter in SI units is 2 10-10 m (200 picometers (pm))
In each shell, beginning with the second, there are three mutually
perpendicular p orbitals, px, py, and pz, of equal energy
Lobes of p orbitals are separated by region of zero electron density, a
node
Each lobe has a different algebraic sign, + and -, represented by
different colors
Algebraic signs are not charges
Ionic compounds
Some elements achieve an octet configuration by gaining or
losing electrons
Ions form when an electron is gained or lost from a neutral atom
Ions are charged because they have different numbers of protons
and electrons
Ions are held together by an electrostatic attraction, like in Na+ Cl, forming an ionic bond
Molecular compounds
Achieve their octet by sharing electrons between atoms via
covalent bonds
Most organic compounds are molecular compounds
H (1s) needs one more electron to attain (1s2) and forms one bond
N (2s22p3) needs three more electrons to attain (2s22p6) and forms
three bonds
Lone-pair electrons
All four carbon-hydrogen bonds in methane are identical and are spatially
oriented toward the corners of a regular tetrahedron
sp hybrid orbital
A hybrid orbital derived from
the combination of one s and
one p atomic orbital
The two sp hybrids are
separated by an angle of 180
Two 2p orbitals remain nonhybridized
Methylamine CH3NH2
Methyl alcohol
Bonds are close to the109.5 tetrahedral angle
Two of the four sp3 hybrid orbitals on oxygen are occupied by
nonbonding electron lone pairs