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Biochemicals
• Organic chemistry is the study of the
compounds of carbon not classified as
inorganic
• Of the several million known compounds of
carbon, only a very few are not organic
• Carbon atoms are unique because they form
strong covalent bonds with each other while
at the same time binding atoms of other
nonmetals strongly
• Isomers are compounds with identical
molecular formulas, but whose molecules
have different structures
• Organic compounds are rich in isomers
Formula Number of Isomers
C8H18 18
C10H22 75
C20H42 366,319
C40H82 6.25x1013 (estimated)
• Organic families are defined by functional
groups
• Functional groups are small structural units
within a molecule at which most of the
compound’s reactions occur
• Condensed structures are usually used to
represent organic molecules
• C-H bonds are usually understood
• Lone pairs of electrons are not shown
• These saves both time and space when writing
formulas
Characteristic
Family Feature Example Some Important Families
Alkanes only single bonds CH 3CH 3
of Organic Compounds
Alkenes C=C CH 2 = CH 2
Alkynes C≡C CH ≡ CH
Alcohols ROH CH 3CH 2 OH
Ethers ROR' CH 3OCH 3
O O
|| ||
Aldehydes RCH CH 3 C H
O O
|| ||
Ketones R C R' CH 3 C CH 3
O O
|| ||
Carboxylic acids R C OH CH 3 C OH
O O
|| ||
Esters R C OR' CH 3 C OCH 3
Amines RNH 2 CH 3 NH 2
More general forms of
O O
both amines and amides
Amides
||
R C NH 2 CH 3 C NH 2
||
exist.
R and R' represent any alkyl (purely alkine - like) group
• An advantage to collecting molecules into
families is that only a few kinds of reactions
must be learned
• The emphasis is on the properties of the
functional group, not individual molecules
• Once the center of reactivity is identified, its
characteristic reactions are generally
expected to occur
Carbon atoms can be
found in continuous
sequences (called
straight chained
molecules) or with
“branches” off the
main chain (called
branched
compounds).
• Carbon can also form rings
Rings are often
represented as
polygons where
the corners
represent carbon
atoms. Heterocylic
rings contain
atoms other than
carbon, called
heteroatoms.
• The functional groups and size, for
example, determine if a molecule is soluble
in water
– Hydrocarbons are only slightly polar and tend
to be insoluble in water
• These include alkanes, alkenes, alkynes, and
aromatic compounds
– Molecules with polar functional groups tend to
be soluble in water
• These include alcohols, carboxylic acids, amines,
and amides
– Large molecules, even if they contain polar
functional groups, tend to be insoluble
• Alkanes are hydrocarbons that contain only
single bonds
• They are called saturated compounds
• Hydrocarbons with double or triple bonds
(alkenes, alkynes, and aromatic compounds)
are called unsaturated compounds
• Many hydrocarbons come from fossil fuels
(coal, petroleum, and natural gas)
• One operation in petroleum refining is to
boil the crude oil and selectively condense
the vapors between preselected temperature
ranges
• The liquid collected at each range is called a
fraction and the process is called fractional
distillation
• Each fraction is made almost entirely of
alkanes
• For example, gasoline is the fraction collected
between about 40 and 200oC
• All open-chain alkanes have the general
formula CnH2n+2, where n is the number of
carbon atoms in the chain
• Their boiling point increases with mass (see
Table 25.2) as their London forces become
greater with molecular size
• The International Union of Pure and
Applied Chemistry (IUPAC) rules for
organic nomenclature are very systematic
• IUPAC rules for naming the alkanes
1) The name ending for all alkanes is –ane.
2) The parent chain is the longest continuous chain
of carbons in the structure.
3) A prefix is added to the name ending –ane to
specify the number of carbon atoms in the parent
chain. The prefixes for up to ten carbons are:
meth- 1 C eth- 2C prop- 3 C
but- 4C pent- 5C hex- 6 C
hept- 7 C oct- 8C non- 9 C
dec- 10 C
4) The carbon atoms are number from the end that
gives the lower of the two possible numbers for the
first branch.
5) Each branch attached to the parent is named as an
alkyl group, which is an alkane with one hydrogen
removed to allow attachment to the parent chain.
The names of alkyl groups end in –yl.
methyl − CH 3 −
ethyl − CH 3CH 2 −
propyl − CH 3CH 2 CH 2 −
isoproply − CH 3 C HCH 3
|
6) The name of each alkyl group is attached to the
name of the parent as a prefix, each is named and
located with a number in front, separating the
number from the name by a hyphen.
7) When two or more groups are attached the parent,
each is named and located with a number. The
names of the alkyl substituents are assembled in
alphabetical order. Use hyphens to separate the
numbers from words.
8) When two or more substituents are identical,
multiplier prefixes are used: di (for 2), tri (for 3),
trtra (4), and so forth. The location number of every
group must appear in the final name. Separate a
number from a number with a comma.
9) When identical groups are on the same atom, the
number of this position is repeated in the name.
CH 3
|
Example : CH 3 − C − CH 2CH 3
|
CH 3
2,2 - dimethylbutane