ISOMERS Flashcards
Compounds having the same molecular formula and same molecular weight but different structural formula, thus differ in physical and chemical properties.
Isomers
Isomer compounds have the same what?
Molecular formula and molecular weight
Isomer compounds differ in what?
Physical and Chemical properties
Isomers have different what?
Structural formula
Molecular Formula is also known as?
Chemical Formula
It gives the proportions of atoms which is present in the molecule or compound.
Molecular Formula (Chemical Formula)
It shows different graphic representation of the molecule and compound.
Structural Formula
Structural Formula types
Expanded, Condensed, Skeletal
2 Dimensional
Structural
3 Dimensional
Stereo
Subtypes of Structural
Chain
Positional
Functional Metamerism
Tautomerism
Ring-chain
Subtypes of Stereo
Geometric
Optical
AKA Constitutional Isomers
Structural Isomerism
Compounds which have the same molecular formula but differ in their structure.
Structural Isomers
Simplest Hydrocarbons
CH4 (Methane)
CH3CH3 (Ethane)
CH3CH2CH3 (Propane)
Which hydrocarbons doesn’t have constitutional isomers?
Simplest hydrocarbons
This hydrocarbon has constitutional isomers.
C4H10 (Butane)
CH4
Methane
CH3CH3
Ethane
CH3CH2CH3
Propane
C4H10
Butane
meaning of ( n ) in n-butane
normal and straight chain
prefix “iso” is used when?
the structure is branched
iso meaning
isomer
isomer is used usually on
2-methylalkanes
This isomers differ in the chain of the carbon atoms.
Chain Isomers
other name of isobutane
2-methylpropane
prefix “neo” is used when
second to the last carbon is tri-substituted
IUPAC name of neopentane
2,2-dimethylpropane
These isomers differ in the type of functional group.
Functional Isomers
Has the same molecular formula but differs in functional group.
Functional Isomers
These isomers differ in the attachment of the functional group to the chain at different positions.
Positional Isomers
This type of isomerism arises due to the presence of different alkyl chains on each side of the functional group.
Metamers
It is a rare type of isomerism and is generally limited to molecules that contain a divalent atom (such as sulfur or oxygen), surrounded by alkyl groups.
Metamers
Divalent atoms
Sulfur / Oxygen
Metamers examples
Ethers
Thioethers
Ketone
Isomer of the compound which only differs in the position of protons and electrons.
Tautomers
It occurs via an intramolecular proton transfer.
Tautomers
Tautomers important example is
Keto-enol tautomerism
⇌
reversible
Has carbonyl carbon.
Keto form
Has presence of double bond and hydroxyl group.
Enol form
Keto form is _____ stable?
More stable 99.9%
Enol form is ____ stable
less stable 0.001%
Tautomerism examples
Ketone-enol
Enamine-Imine
Lactam-Lactim
One of the isomers has an open-chain structure whereas the other has a ring structure.
Ring-chain Isomers
A great example of ring-chain isomers can be observed in?
C3H6 (Propene)
Isomers that have the same composition (that is, the same parts) but that differ in the orientation of those parts in space.
Stereoisomers
Isomers that differ in the spatial arrangement of atoms rather than order of atomic connectivity.
Stereoisomerism
Geometrical Isomers is popularly known as?
cis-trans isomerism
These isomers have different spatial arrangement of atoms in three dimensional space.
Geometrical Isomers
This isomer is the one having identical groups on same side of double bond.
cis-isomer
This isomer has identical groups on opposite side.
trans-isomer
Does not permit rotation.
π bond in alkenes
- double bond
- has 2 diff groups
Geometrical Isomers (cis-trans)
Cis meaning in Latin
this side of
Trans meaning in Latin
the other side of
“Cis” equivalent in German
Zusammen
“Trans” equivalent in German
Entgegen
Trans-fat has high MP so it does not melt easily.
Narrowing of blood vessels
Vasoconstriction
trans-fat can be found in
fast food meals
Geometric Isomers can be identified by using
cis-trans nomenclature
E-Z Notational System substituent rule
CAHN-INGOLD-PRELOG (CIP sequence rule)
In E-Z Notational System, higher is the priority if it has
larger MW
In E-Z Notational System, lower is the priority if it has
small MW
Isotope of Hydrogen
deuterium > protium
(tritium is not usually used)
Highest atomic number
Iodine
Lowest atomic number
Hdyrogen
These are compounds having at least one carbon atom joined to four different atoms or groups.
Optical Isomers
Such carbon atom with four different atoms or groups is called?
Asymmetric / Chiral Carbon Atom
Those carbons that do not have four different groups are called?
Achiral
Other names for chiral carbon
Stereocenter
Stereogenic center
- absolute configuration
- how atoms attached around a chiral center
S - R enantiomer
S meaning in S-R (Latin)
Sinister (Counterclockwise/Left)
R meaning in S-R (Latin)
Rectus (Clockwise/Right)
2nd to the last carbon is called
Penultimate Carbon
How it rotates a plane of polarized light.
D - L Configuration
D meaning in D-L
Dextro
L meaning in D-L
Levo
Ability of the object to be placed to another object without visibility restriction.
Superimposable (Specific) / Superposable (General)
Mirror image and non superimposable.
Enantiomer
non-mirror and non-superimposable
Diastereomers
Diastereomers example
D-glucose
D-galactose
If the hydroxyl group is on the right side
Dextro
If the hydroxyl group is on the left side
Levo
Have identical physical properties except optical activity.
Optical Isomers
They rotate the plane of polarized light in opposite directions.
Optical Isomers
In optical isomers, the ___________ is defined as the light that vibrates in one plane only.
plane polarized light
The rotation of the plane of polarized light is called _______?
optical activity
50% dextro & 50% levo
racemic mixture
Compounds that rotate the plane of plane polarized light to the right (clockwise) are said to be?
Dextrorotatory
Compounds that rotate the plane to the left (counterclockwise) are called?
Levorotatory
Approximately ____ of marketed drugs are chiral.
50%
The two enantiomers of a chiral drug may different significantly. It may have ______ differences or _______ differences
Pharmacokinetics & Pharmacodynamics
What the body does to the drug.
Pharmacokinetics
What a drug does to the body.
Pharmacodynamics
Pharmacokinetics ADME meaning
Absorption
Distribution
Metabolism
Excretion
Warfarin uses
anticoagulant (blood thinners)
increase clotting time
increase +½
less distributed
less potent
R Warfarin
decrease +½
more distributed
more potent
S Warfarin
Qunatity of drug necessary to give effect.
Potency
pharmacologically active
S ibuprofen
no anti-inflammatory
R ibuprofen
Ibuprofen uses
NSAID (Non-steroidal anti-inflammatory drug)
NSAID OTC mg
100mg, 200mg
NSAID Rx mg
400,600, 800
Teratogenic
Thalidomide
sedative
for morning sickness
R thalidomide
Shortened limbs of babies.
Phocomelia