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Carbides
Carbonates
Simple oxides of Carbon
Cyanides
Modern classification
Even though vitalism has been discredited, scientific nomenclature retains the distinction
between organic and inorganic compounds. The modern meaning of organic compound is any
compound that contains a significant amount of carboneven though many of the organic
compounds known today have no connection to any substance found in living organisms.
There is no single "official" definition of an organic compound. Some textbooks define an
organic compound as one that contains one or more C-H bonds. Others include C-C bonds in
the definition. Others state that if a molecule contains carbonit is organic.
Even the broader definition of "carbon-containing molecules" requires the exclusion of carboncontaining alloys (including steel), a relatively small number of carbon-containing compounds
such as metal carbonates and carbonyls, simple oxides of carbon and cyanides, as well as the
allotropes of carbon and simple carbon halides and sulfides, which are usually considered
inorganic.
The "C-H" definition excludes compounds that are historically and practically considered
organic. Neither urea nor oxalic acid is organic by this definition, yet they were two key
compounds in the vitalism debate. The IUPAC Blue Book on organic nomenclature specifically
mentions urea and oxalic acid. Other compounds lacking C-H bonds that are also traditionally
considered organic include benzenehexol, mesoxalic acid, and carbon tetrachloride. Mellitic
acid, which contains no C-H bonds, is considered a possible organic substance in Martian soil. CC bonds are found in most organic compounds, except some small molecules like methane and
methanol, which have only one carbon atom in their structure.
The "C-H bond-only" rule also leads to somewhat arbitrary divisions in sets of carbon-fluorine
compounds, as, for example, Teflon is considered by this rule "inorganic" but Tefzel organic.
Likewise, many Halons are considered inorganic, whereas the rest are considered organic. For
these and other reasons, most sources believe C-H compounds are only a subset of "organic"
compounds.
In summary, most carbon-containing compounds are organic, and almost all organic
compounds contain at least a C-H bond or a C-C bond. A compound does not need to contain CH bonds to be considered organic (e.g., urea), but many organic compounds do.
Carbon
C
nonmetallic
atomic number: 6
electronic configuration: 1s22s22p2
valence electrons: 4
tetravalent capable of four covalent bonds
has the unique ability to bond together, forming long chains and rings
History
In 1770, Torbern Bergman was the first to express the difference between inorganic and
organic substances, and the term organic chemistry soon came to mean the chemistry of
compounds from living organisms.
Before the nineteenth century, chemists generally believed that compounds obtained from
living organisms were endowed with a vital force that distinguished them from inorganic
compounds. According to the concept of vitalism (vital force theory), organic matter was
endowed with a "vital force". During the first half of the nineteenth century, some of the first
systematic studies of organic compounds were reported. Around 1816, Michel Chevreul started
a study of soaps made from various fats and alkalis. He separated the different acids that, in
combination with the alkali, produced the soap. Since these were all individual compounds, he
demonstrated that it was possible to make a chemical change in various fats (which
traditionally come from organic sources), producing new compounds without "vital force". In
1828, Friedrich Whler produced the organic chemical urea (carbamide), a constituent of
urine, from the inorganic ammonium cyanate NH4CNO, in what is now called the Whler
synthesis. He showed that organic compounds can be produced from inorganic compounds.
Vitalism
The word organic is historical, dating to the 1st century. For many centuries, Western
alchemists believed in vitalism. This is the theory that certain compounds could be synthesized
only from their classical elementsearth, water, air, and fireby the action of a "life-force"
(vis vitalis) that only organisms possessed. Vitalism taught that these "organic" compounds
were fundamentally different from the "inorganic" compounds that could be obtained from the
elements by chemical manipulation.
Properties
Physical properties of organic compounds typically of interest include both quantitative and
qualitative features. Quantitative information includes melting point, boiling point, and index of
refraction. Qualitative properties include odor, consistency, solubility, and color.
Solubility
Neutral organic compounds tend to be hydrophobic; that is, they are less soluble in water
than in organic solvents. Exceptions include organic compounds that contain ionizable (which
can be converted in ions) groups as well as low molecular weight alcohols, amines, and
carboxylic acids where hydrogen bonding occurs. Organic compounds tend to dissolve in
organic solvents. Solvents can be either pure substances like ether or ethyl alcohol, or mixtures,
such as the paraffinic solvents such as the various petroleum ethers and white spirits, or the
range of pure or mixed aromatic solvents obtained from petroleum or tar fractions by physical
separation or by chemical conversion. Solubility in the different solvents depends upon the
solvent type and on the functional groups if present.
Solid state properties
Various specialized properties of molecular crystals and organic polymers with conjugated
systems are of interest depending on applications, e.g. thermo-mechanical and electromechanical such as piezoelectricity, electrical conductivity (see conductive polymers and
organic semiconductors), and electro-optical (e.g. non-linear optics) properties. For historical
reasons, such properties are mainly the subjects of the areas of polymer science and materials
science.
Inorganic
many boil
insoluble/hydrophobic
soluble/hydrophilic
flammable
non-flammable
Hybridization
It occurs when an atom bonds using electrons from both the s and p orbitals (s orbitals are
lower in energy than p orbitals), creating an imbalance in the energy levels of the electrons
and to equalize these energy levels, the s and p orbitals involved are combined to create hybrid
orbitals.
In other words, hybridization is the mixing of a set of unequal orbitals to obtain a new set of
equal orbitals with properties somewhere between the original unequal orbitals.
*Orbitals it is the region of space where there is a high probability of finding an electron in
an atom
*sigma bond
strongest type of covalent bond
formed by head-on overlapping between atomic orbitals
allows free rotation
*pi bond
covalent chemical bonds where two lobes of one involved atomic orbital overlap
sideways two lobes of the other involved atomic orbital
restricts rotation
Orbitals
Characteristics
s orbital
spherical shape
p orbital
loop-shaped
sp orbital
sp2 orbital
sp orbital
1 s and 1 p orbital
2 sigma bonds present
2 unhybridized p orbital
surrounded by at least a a triple bond
linear (180)
1 s and 2 p orbital
3 sigma bonds present
1 unhybridized p orbital
surrounded by at least a double bond
trigonal planar (120)
1 s and 3 p orbitals
4 sigma bonds present
no unhybridized p orbital
surrounded by single bonds
tetrahedral (109.5)
1.
2.
3.
4.
5.
6.
s sp2
s sp2
sp2 sp2
pp
sp2 s
sp2 s
Alkanes
Condensed
Formula
Methane
CH4
Ethane
CH3CH3
Propane
CH3CH2CH3
Butane
CH3(CH2)2CH3
Pentane
CH3(CH2)3CH3
Hexane
CH3(CH2)4CH3
Heptane
CH3(CH2)5CH3
Octane
CH3(CH2)6CH3
Nonane
CH3(CH2)7CH3
Decane
CH3(CH2)8CH3
Structural
Functional
Group
Simplest
Compound
Formula
Alkane
Methane
(CH4)
Alcohol
Methanol
(CH4O)
Thiol
Methanethiol
(CH4S)
Amine
Methylamine
(CH5N)
Aldehyde
Methanal
(CH2O)
Carboxylic Acid
Methanoic acid
(CH2O2)
Ester
Methyl Methanoate
(C2H4O2)
Ether
Dimethyl ether
(C2H6O)
Ketone
2-propanone
(C3H6O)
Alkene
Ethylene
(C2H4)
Alkyne
Ethyne
(C2H2)
Amide
Ethanamide
(C2H5NO)
Chloroform
(CHCl3)
Carbon tetrachloride
(CCl4)
Alkyl Halide
Forms of formula
Molecular formula
Line-angle formula
Functional Groups
These are specific groups of atoms or bonds within molecules (covalently bonded with C
atoms) that are responsible for the characteristic chemical reactions of those molecules. The
same functional group will undergo the same or similar chemical reaction(s) regardless of the
size of the molecule it is a part of. However, its relative reactivity can be modified by nearby
functional groups.
The functional group gives the molecule its properties, regardless of what molecule contains
it; they are centers of chemical reactivity. The functional groups within a molecule need to be
identified when naming. It can be used to predict the chemical behavior or reactivity of a
biomolecule.
The unique functional groups present on a biomolecule determine reactivity, solubility, and
other physical properties that lead to its biological role in living organisms. Understanding how
common functional groups affect chemical reactivity improves our ability to understand the
chemical behavior and cellular roles of all biomolecules.
1. Hydrocarbons
Alkanes
simplest organic molecules because it consists only of C-H single bonds
have single bonds therefore saturated
used as the basis for naming the majority of organic compounds (their
nomenclature)
general formula: CnHn+2
Alkenes
Alkynes
unsaturated hydrocarbons that contain at least one triple bond between
two C atoms
general formula: CnH2n-2
Aromatic Hydrocarbons
has benzene rings (consists of alternating double and single bonds)
cyclic (forms rings)
*Benzene
*Cycloalkanes types of alkanes that have one or more rings connected by single bonds of C
atoms in the chemical structure of their molecules. General formula: CnH2n
2. Oxygen-containing
Alchohol
Carboxylic acid
Ether
Ester
Ketone
Aldehyde
3. Nitrogen-containing
Amines
Amides
4. Sulfur-containing
Thiols
5. Halogen-containing
Alkyl halides or haloalkanes
*general formulae of hydrocarbons apply to compounds with only one of their specified bond
and no other functional groups present
Functional
Group
Prefix
Carboxylic Acid
Suffix
-oic acid
Ester
alkoxycarbonyl-
-oate
Amide
amido-
-amide
Aldehyde
oxoformyl-
-al
Ketone
oxo-
-one
Alcohol
hydroxy-
-ol
Thiol
mercapto-
-thiol
Amine
amino-
-amine
Alkene
alkenyl-
-ene
Alkyne
alkynyl-
-yne
Alkane
alkyl-
-ane
Ether
alkoxy-
ether
Alkyl Halide
halo-
Nitro
nitro-
*structural formulae are general formulae without the R but SF of hydrocarbons is shown instead
Isomerism
Isomerism is the phenomenon whereby certain compounds, with the same molecular formula,
exist in different forms owing to their different organizations of atoms or their spatial
arrangement.
1. Structural Isomerism - molecules have the same molecular formula but different
structural formula
a. Chain isomerism different C skeletons
b. Position isomerism different position of functional groups
c. Functional group isomerism different functional groups
2. Stereoisomerism molecules have the same molecular formula and bond order but
different spatial arrangements
a. Geometric isomerism
also cis-trans isomerism
involves double bonds that do not allow free rotation
b. Optical isomerism
exist in pairs, in which one isomer is the mirror image of the other
*see examples
Conformations
Conformations are an atomic spatial arrangements that results from rotation of carbon atoms
about single bonds within an organic molecule
Conformational isomers - isomers where the atoms and connectivity remains the same, but
can be interconverted to one another by rotation around a single bond
Newman projection - visualizes chemical conformations of a carbon-carbon chemical bond
from front to back, with the front carbon represented by a dot and the back carbon as a circle
*Torsional strain or the eclipsing strain; is the increase in potential energy of a molecule due
to repulsion between electrons in bonds that do not share an atom
Puckered conformations slight deviations from planar conformations
Cyclobutane
Cyclopentane
Ortho, Meta, and Para structures
Electron delocalization distribution of density of the electrons that are not directly associated
with a single atom and can freely move around the compound
Electron delocalization is present in benzene rings.
electrons, making them localized or isolated. If the electron density is not similar within the
compound, also considering electron repulsion, the compound is not stable.
First step is always to find the parent chain which is the longest carbon chain.
Substituents are arranged alphabetically in the nomenclature of organic compounds,
disregarding the prefixes.
Alkyl group - group of carbon and hydrogen atoms derived from an alkane molecule by
removing one hydrogen atom
Alkanes have single bonds
Alkenes have double bonds
The presence of pi bonds restricts rotation. The different spatial arrangements of two
comparable substituents create different properties. Cis-trans naming is used.
Alkynes have triple bonds
In cases of multiple functional groups present in a compound, the one with higher
priority gets the lower locant and credits for the last name of the compound.
Write down the locants as you count the carbon chain.
Always check the affixes.
Substituents with lower priority use their prefixes.
A hydroxyl is a chemical functional group containing an oxygen atom connected by a
covalent bond to a hydrogen atom. (OH)
Carboxylic acids are always in the terminal carbon. The locant is not needed anymore.
Ethers and thiols are derivatives of alcohol.
Ketones and aldehydes both have carbonyl group.
A carbonyl group is a functional group composed of a carbon atom double-bonded to
an oxygen atom: C=O.
Aldehydes are always in the terminal carbon. Therefore, locant is not needed to be
stated anymore.
Double-bonded O in aldehydes are only located if the aldehyde group in the compound
is the lesser subsituent.
Carboxylic acids have the carboxyl group. They are always terminal. No locant is needed.
The carboxyl group is an organic functional group consisting of a carbon atom double
bonded to an oxygen atom and single bonded to a hydroxyl group.
In case of multiple carboxyl groups are present in a compound, the C in the carboxyl
groups are not counted to the mother chain.
Esters have no locants.
Amines are derivatives of ammonia (NH3).
Locants are needed on disubstituted benzene, and not on monosubstituted.
Phenyl- - used when bezene is considered as the substituent.
For hydrocarbons:
1. function group through the bonds
2. number of similar bonds
3. number of C in the mother chain
4. substituents
5. number of similar substituents
6. location of the substituents
For other functional groups (general):
1. functional groups present
2. higher prioritized functional group
3. number of C present in the mother chain
4. location of the functional group
5. lesser prioritized functional group / substituent
6. number of similar substituents
7. location of the subsituents
Ethers
1. shorter and longer R
Ketones
1. location of the double-bonded O
Esters
1. single-bonded O
2. double-bonded O