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Organic Chemistry
Isomerism
01. ORGANIC SERIES 01.1. Homologous series: is a set of organic compounds with t
he same function, which differ in one or more CH2 groups. Eg methane, ethane., P
ropane, butane (CH4, C2H6, C3H8, C4H10); General Formula: CnH2n +2. Methanol, et
hanol, 1-propanol, 1-butanol (CH4O, C2H6O, C3H8O; C4H10O) General Formula: CnH2n
+2 O. Note: The physical properties of compounds of a homologous series vary un
iformly; 1.2. SERIES isóloga: is a set of organic compounds from the same funct
ion that differ in one or more H2. Eg ethane, ethene; etin (C2H6, C2H4, C2H2) cy
clopentane; Cyclopentene; cyclopentadiene (C5H10, C5H8, C5H6). 3.1. Heterologous
SERIES: is a set of compounds from different bodily functions, but having in co
mmon the same number of carbon atoms. Eg toluene, benzoic acid, benzoic aldehyde
, phenyl cyanide (C6H8, C6H6O, C6H6O2; C6H5N).
02. Isomerism isomerism: is the phenomenon whereby the same group of atoms gives
rise to different substances due to different atomic arrangements. Isomers: are
compounds with the same molecular formula but with different atomic arrangement
s, so with different properties. Isomerism Plana: is one in which the compounds
have different structural formulas flat, so the difference of the compounds is v
isible in the plan. Isomerism space: it is one in which the compounds have the s
ame formula flat, but different spatial structures. Note: The Isomerism can be P
lain or Space. The Isomerism Plana can be: string, position, compensation or met
amerism, function or functional, dynamic or tautomerism. The Isomerism Space is
divided into Geometric Isomerism and Cis-Trans Isomerism and Optical.
1.2. Isomerism FLAT I) chain Isomerism: characterized by having the same functio
n organic isomers that have different numbers of carbon atoms in the main chain.
Note: In the case of cyclic compounds such isomerism can also be called isomeri
sm core or ring;
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II) isomers of position: it is characterized by having the same function organic
isomers that have the same backbone, but contain functional groups or double an
d triple bonds in different positions; III) Isomerism of compensation or metamer
ism: characterized by having isomers of the same organic function, but presents
a heteroatom in different positions in the carbon chain; Note: Heteroatom is a d
ifferent carbon atom between two carbons, usually: O, S, N, P etc.. Note: Hydrog
en will never be a heteroatom; IV) or Functional Isomerism function: characteriz
ed by having different isomers of bodily functions. Eg aldehyde and ketone, carb
oxylic acid and ester, phenol and aromatic ether and aromatic alcohol. V) or iso
mers dynamic tautomerism: characterized by having different isomers of bodily fu
nctions, but which are transformed into each other in solution, through a dynami
c balance. Note: It usually occurs between: and enol aldehyde (aldo-enol equilib
rium), ketone and enol (keto-enol equilibrium). Note: enol is an organic functio
n characterized by the presence of hydroxyl (OH) attached to a carbon double bon
d, which differentiates it from an alcohol, because as we have hydroxyl attached
to carbon saturated.
2.2. SPACE OR isomerism Stereoisomerism 02.2.1. Isomerism GEOMETRIC OR CIS-TRANS
I) In an acyclic compounds occurs when atoms or groups of different atoms are j
oined to each of the carbon atoms of a double bond.
Note: This pair of similar structures is chemically different, since one molecul
e can not be converted into another because of hindered rotation between the car
bons. Note: in compounds that have four different ligands on carbons rotation pr
evented, it is the CIS isomer that contains the larger groups on the same side.
Note: in general, the cis-trans isomers have the same chemical properties but ha
ve different physical properties. The chemical properties are different when you
depend on the relative positions of the groups if these positions are different
, the chemical properties of the isomers also will be. Note: It appears that the
trans forms are more stable than their cis forms, which can be explained by the
smaller repulsion between the groups in the trans position. II) In compounds Ch
ain Cyclic (Isomerism of Baeyer or Baeyeriana)
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When carbon atoms are linked in a cycle can never undergo a full rotation on the
throne of their axis without breaking the cycle, then geometric isomerism so th
at there is enough that at least two carbon cycle ligands possess different.
2.2. 2. Optical isomer optical isomers: those whose only difference is the behav
ior in front of a polarized light (polarized light is one that vibrates in one d
irection). For an organic compound is optically active is necessary that its mol
ecules is asymmetric, ie, its molecules must possess asymmetric carbon, which is
the carbon that has four different ligands, namely carbon double bond or triple
can never be asymmetric . The asymmetric or chiral carbon is represented by C *
. Optically active substance: it is one that deviates from the plane of polarize
d light, if the deviation is to the right say it is dextrorotatory and the devia
tion is to the left say it is levorotatory. Optically inactive substance: it is
one that does not divert the plane of polarized light. Racemic mixture: it is op
tically inactive for external compensation, ie as there are equal numbers of mol
ecules causing deviations in the opposite polarized light, one cancels the other
and the deviation of the final deviation is zero. Enantiomorfos, Antipodes or o
ptical enantiomers: are compounds that are mirror images of each other, ie are n
ot superimposed, deviate polarized light from the same angle (active), but for o
pposite sides. Diasteroisomers: optical isomers are not enantiomorfos among them
selves, or are not mirror images of each other and deviate polarized light at di
fferent angles (assets) and only occur in compounds with more than a C * in the
molecule. Note: the right and left hands are mirror images of one another and ar
e not overlapping, so they are asymmetrical. Meso isomer: isomer is inactive by
internal compensation, ie a compound that has two asymmetric carbons (2C *) with
the same ligand and one of carbons deviates polarized light at an angle α to t
he right and the other C * bends light polarized at an angle α to the left, so
the final deviation is zero. 1. No Case: Molecules with a C * has three isomers:
 a dextrorotatory, levorotatory and racemic one (formed by equimolar amounts of
dextrorotatory and levorotatory). 2. No Case: Molecules with two equal C *: they
have four isomers: a dextrorotatory, levorotatory one, a meso and a racemic or
mesógiro (inactive by internal compensation). 3. No Case: Molecules that have "
n" different asymmetric carbons: A. No active optical isomers: 2n (Note: Formula
s Van't Hoff) B. No bouncing of optical isomers: 2n-1 (which corresponds to half
the assets, because those come together in pairs to form the corresponding inac
tive) C. No dextrorotatory optical isomers: 2n-1 (which corresponds to half of
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assets) D. No levorotatory optical isomers: 2n-1 (which corresponds to half the
assets) E. No racemic mixture: 2n-1 (which corresponds to half the assets) F. No
. of optical isomers: 2n + 2n-1 or 3. 2n-1 (which corresponds to the sum of asse
ts with inactive)
I - Asymmetric Molecules that do not have an Asymmetric Carbon. No Case: molecul
es or compounds accumulated Diene Diene Alenia The earnings are compounds that c
ontain two double bonds followed.
Observing the spatial geometry of these types of compounds we find that they do
not have a plane of symmetry, ie they are asymmetric, exhibit optical activity a
nd thus have two isomers, the dextrorotatory and levorotatory and therefore a ra
cemic mixture. 2. No Case: Trans Isomerism in Cyclic Molecules. When a compound
of carbon chain cyclic presents geometric isomer, trans isomer of the molecule i
s asymmetric, ie has no plane of symmetry and thus has optical activity, showing
two isomer, dextrorotatory, the levorotatory and also a racemic mixture.
Note: The cis isomer has symmetry plane, so it is optically inactive.
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