This document provides information about stereochemistry and optical isomers. It defines different types of isomers such as structural isomers, stereoisomers, enantiomers, and diastereomers. It discusses how compounds can be optically active and how a polarimeter is used to measure optical activity. The R/S system and Cahn-Ingold-Prelog rules for assigning configurations at chiral centers are also explained. The document outlines how reactions involving chiral compounds can result in retention, inversion, or a mixture of configurations depending on whether bonds to the chiral center are broken in the reaction.
Unit i.Optical Isomerism as per PCI syllabus of POC-III Ganesh Mote
Unit I optical isomerism which is included in PCI syllabus of Sem IV of POC-III subject
This Unit Includes all points of Unit I such as nomenclature, R& S, d&l, D& L isomerism, Meso compounds, diastereomers, chirality, resolution of racemic mixture, enantiomers, Asymmetric synthesis,
Unit i.Optical Isomerism as per PCI syllabus of POC-III Ganesh Mote
Unit I optical isomerism which is included in PCI syllabus of Sem IV of POC-III subject
This Unit Includes all points of Unit I such as nomenclature, R& S, d&l, D& L isomerism, Meso compounds, diastereomers, chirality, resolution of racemic mixture, enantiomers, Asymmetric synthesis,
This worksheet gives pupils practice with adding up relative atomic masses to obtain relative molecular mass. Pupils will need a data sheet or a list of relative atomic masses to be able to complete the questions.
chemical lab report:Synthesis and properties of a cobalt cage complexAwad Albalwi
In this experiment [Co(diNOsar)]Br 3 is synthesised from [Co(en) 3 ]Br 3 in the
presence of formaldehyde, nitromethane and sodium carbonate. A yield of
36.7% was obtained for the [Co(diNOsar)]Br 3 .The electrochemical properties
of Co(diNOsar)]Br 3 , [Co(en) 3 ]Br 3 and [Co(sepulchrate)]Br 3 were investigated
by using cyclic voltammetry . The CV spectra of the [Co(en) 3 ]Br 3 complex has
shown clearly reduction of the Co(III) ion to Co(II) ion .However, there is no
reversible oxidation of the Co(II) ion to Co(III) ion. The reason for irreversible
oxidation the Co(II) ion might due to the Co(II) complex exchanging ligands
Optical activity in catenanes and rotaxanesPRUTHVIRAJ K
These class of compounds do not contain any formal chiral centre but exhibit stereoisomerism due to presence of either a chiral axis or a chiral plane and are called stereoaxis and stereoplanes respectively
Worksheet for practicing working out empirical formulae. Pupils will need a data sheet or a list of relative atomic masses to be able to complete the questions.
This worksheet gives pupils practice with adding up relative atomic masses to obtain relative molecular mass. Pupils will need a data sheet or a list of relative atomic masses to be able to complete the questions.
chemical lab report:Synthesis and properties of a cobalt cage complexAwad Albalwi
In this experiment [Co(diNOsar)]Br 3 is synthesised from [Co(en) 3 ]Br 3 in the
presence of formaldehyde, nitromethane and sodium carbonate. A yield of
36.7% was obtained for the [Co(diNOsar)]Br 3 .The electrochemical properties
of Co(diNOsar)]Br 3 , [Co(en) 3 ]Br 3 and [Co(sepulchrate)]Br 3 were investigated
by using cyclic voltammetry . The CV spectra of the [Co(en) 3 ]Br 3 complex has
shown clearly reduction of the Co(III) ion to Co(II) ion .However, there is no
reversible oxidation of the Co(II) ion to Co(III) ion. The reason for irreversible
oxidation the Co(II) ion might due to the Co(II) complex exchanging ligands
Optical activity in catenanes and rotaxanesPRUTHVIRAJ K
These class of compounds do not contain any formal chiral centre but exhibit stereoisomerism due to presence of either a chiral axis or a chiral plane and are called stereoaxis and stereoplanes respectively
Worksheet for practicing working out empirical formulae. Pupils will need a data sheet or a list of relative atomic masses to be able to complete the questions.
Chirality and its biological role (English language) - www.wespeakscience.comZeqir Kryeziu
This presentation focuses on organic chemistry, especially stereochemistry for 3D shape of molecules. When the same chemical substance differs in its spatial construct it changes in a drastic way its own features, in a biological environment.
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How to Make a Field invisible in Odoo 17Celine George
It is possible to hide or invisible some fields in odoo. Commonly using “invisible” attribute in the field definition to invisible the fields. This slide will show how to make a field invisible in odoo 17.
Read| The latest issue of The Challenger is here! We are thrilled to announce that our school paper has qualified for the NATIONAL SCHOOLS PRESS CONFERENCE (NSPC) 2024. Thank you for your unwavering support and trust. Dive into the stories that made us stand out!
2024.06.01 Introducing a competency framework for languag learning materials ...Sandy Millin
http://sandymillin.wordpress.com/iateflwebinar2024
Published classroom materials form the basis of syllabuses, drive teacher professional development, and have a potentially huge influence on learners, teachers and education systems. All teachers also create their own materials, whether a few sentences on a blackboard, a highly-structured fully-realised online course, or anything in between. Despite this, the knowledge and skills needed to create effective language learning materials are rarely part of teacher training, and are mostly learnt by trial and error.
Knowledge and skills frameworks, generally called competency frameworks, for ELT teachers, trainers and managers have existed for a few years now. However, until I created one for my MA dissertation, there wasn’t one drawing together what we need to know and do to be able to effectively produce language learning materials.
This webinar will introduce you to my framework, highlighting the key competencies I identified from my research. It will also show how anybody involved in language teaching (any language, not just English!), teacher training, managing schools or developing language learning materials can benefit from using the framework.
Operation “Blue Star” is the only event in the history of Independent India where the state went into war with its own people. Even after about 40 years it is not clear if it was culmination of states anger over people of the region, a political game of power or start of dictatorial chapter in the democratic setup.
The people of Punjab felt alienated from main stream due to denial of their just demands during a long democratic struggle since independence. As it happen all over the word, it led to militant struggle with great loss of lives of military, police and civilian personnel. Killing of Indira Gandhi and massacre of innocent Sikhs in Delhi and other India cities was also associated with this movement.
Students, digital devices and success - Andreas Schleicher - 27 May 2024..pptxEduSkills OECD
Andreas Schleicher presents at the OECD webinar ‘Digital devices in schools: detrimental distraction or secret to success?’ on 27 May 2024. The presentation was based on findings from PISA 2022 results and the webinar helped launch the PISA in Focus ‘Managing screen time: How to protect and equip students against distraction’ https://www.oecd-ilibrary.org/education/managing-screen-time_7c225af4-en and the OECD Education Policy Perspective ‘Students, digital devices and success’ can be found here - https://oe.cd/il/5yV
This is a presentation by Dada Robert in a Your Skill Boost masterclass organised by the Excellence Foundation for South Sudan (EFSS) on Saturday, the 25th and Sunday, the 26th of May 2024.
He discussed the concept of quality improvement, emphasizing its applicability to various aspects of life, including personal, project, and program improvements. He defined quality as doing the right thing at the right time in the right way to achieve the best possible results and discussed the concept of the "gap" between what we know and what we do, and how this gap represents the areas we need to improve. He explained the scientific approach to quality improvement, which involves systematic performance analysis, testing and learning, and implementing change ideas. He also highlighted the importance of client focus and a team approach to quality improvement.
The Roman Empire A Historical Colossus.pdfkaushalkr1407
The Roman Empire, a vast and enduring power, stands as one of history's most remarkable civilizations, leaving an indelible imprint on the world. It emerged from the Roman Republic, transitioning into an imperial powerhouse under the leadership of Augustus Caesar in 27 BCE. This transformation marked the beginning of an era defined by unprecedented territorial expansion, architectural marvels, and profound cultural influence.
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The French Revolution, which began in 1789, was a period of radical social and political upheaval in France. It marked the decline of absolute monarchies, the rise of secular and democratic republics, and the eventual rise of Napoleon Bonaparte. This revolutionary period is crucial in understanding the transition from feudalism to modernity in Europe.
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3. Isomers – different compounds with the same molecular
formula.
Structural Isomers – isomers that differ in which atoms are
bonded to which atoms.
CH3
eg. C4H10 CH3CH2CH2CH3 CH3CHCH3
n-butane isobutane
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4. Stereoisomers – isomers that differ in the way the atoms are
oriented in space, but not in which atoms are bonded to which
atoms.
eg. cis-2-butene trans-2-butene
H
C C
H3C CH3
H H
C C
H3C H
CH3
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6. optical activity – when a substance rotates the plane of
plane polarized light. (1815 by Biot)
plane polarized light – light that has been passed through
a nicol prism or other polarizing medium so that all of the
vibrations are in the same plane.
non-polarized polarized
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7. polarimeter – an instrument used to measure optical
activity.
light source sample tube
polarizer analyzer
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8. dextrorotatory – when the plane of polarized light is rotated
in a clockwise direction when viewed through a polarimeter.
(+) or (d) do not confuse with D
levorotatory – when the plane of polarized light is rotated in
a counter-clockwise direction when viewed through a
polarimeter.
(-) or (l) do not confuse with L
The angle of rotation of plane polarized light by an optically
active substance is proportional to the number of atoms in the
path of the light.
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9. specific rotation – the angle of rotation of plane
polarized light by a 1.00 gram per cm-3
sample in a 1 dm
tube. [α ]D (D = sodium lamp, λ = 589 mμ).
α
[ α ]D = where α = observed rotation
l * d
l = length (dm)
d = concentration (g/cc)
(+)-alanine [ α ]D = +8.5
(-)-lactic acid [α ]D = -3.8
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10. Why are some substances optically active and others not? Can
we predict which ones will be and which ones won’t?
Louis Pasteur (1848) recrystallized sodium ammonium tartrate
(optically inactive). He noticed that the crystals were of two
types which he physically separated. The two types of crystals
were optically active, but rotated the plane of polarized light in
opposite directions. He proposed that the molecules came in
two forms, “left handed” and “right handed”. Together, the
mixture of the two forms is optically inactive.
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11. enantiomers - mirror-image stereoisomers.
The physical and chemical properties of enantiomers
are identical, except 1) the direction of rotation of the plane of
plane polarized light and 2) how they react with optically
active reagents.
chiral center– is a carbon that is bonded to four different
groups of atoms. (do not confuse with “chiral”)
*
CH3CH2CHBrCH3 (CH3)2CHCH2OH
* *
CH3CHBrCHBrCH3admission.edhole.com
12. configuration – the arrangement in space of the four
different groups about a chiral center.
How do we show configurations?
“wedge” formulas Fischer projections
“cross structures”
use only for chiral centers!
Br
F
HCl
Br
F Cl
H
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13. In the Fischer projection, the horizontal bonds to the chiral
center are always above the plane and the vertical bonds to
the chiral center are below the plane. (the horizontals are
“hugging you.”
CH3
H
Br Cl
CH3
H
ClBr
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14. chiral – not superimposeable on the mirror image
(“handedness”)
achiral – superimposeable on the mirror image; not chiral.
Test for optical activity: chiral molecules are optically
active.
racemic modification – equimolar molar mixture of
enantiomers (will be optically inactive) (+).
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15. - compounds with one chiral center will show optical activity
- compounds without chiral centers do not normally show
optical acitivity
- compounds with more than one chiral center may or may
not show optical activity depending on whether or not they
are non-superimposable on their mirror image (chiral) or
superimposable (achiral).
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16. specification of configuration: The R/S system.
Cahn, Ingold, Prelog sequence rules:
sequence rule 1: the atom attached to the chiral center with
the highest atomic number = 1, next = 2, etc.
sequence rule 2: if the four atoms attached to the chiral
center are not all different, the sequence is determined at the
first point of difference.
sequence rule 3: =X is equal to two –X, etc.
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18. R/S:
1. Using the Cahn, Ingold, Prelog sequence rules, assign
numbers to each of the four groups attached to the chiral
center.
2. Rotate the number 4 group away from you and observe
the sequence 1 2 3 for the remaining groups.
3. If going from 1 2 3 is clockwise, then the
configuration is R (rectus). If the sequence 1 2 3
is counter-clockwise, then the configuration is S
(sinister).
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21. Using R/S problems on the web:
http://chemistry2.csudh.edu/organic/startnewrands.html
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22. Angew. Chem. Int. Ed. Engl. 36, 1057 (1997).
absolute configuration for bromochlorofluoromethane:
Br Br
Cl H H Cl
F F
(R)-(-)- (S)-(+)-
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24. diastereomers – non-mirror image stereoisomers.
(the physical and chemical properties of diastereomers are
different.)
CH3
H Cl
CH2
H Cl
CH3
Cl H
CH2
Cl H
CH3
H Cl
CH2
Cl H
CH3
Cl H
CH2
H Cl
CH3 CH3 CH3 CH3
I II III IV
I & II are enantiomers; III & IV are enantiomers; I & III are
diastereomers; I & IV are diastereomers…
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25. CH3
CH2
H
H Cl
Cl
CH3
C
C
H Cl 14
H,H,H
Cl,C,H
2
3
1
3
2
(S)-
C
C
H Cl 14
C,H,H
3
2
1
2
3
(R)-
Cl,C,H
(2S,3R)-2,3-dichloropentane
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26. CH3
H Cl
CH2
H Cl
CH3
Cl H
CH2
Cl H
CH3
H Cl
CH2
Cl H
CH3
Cl H
CH2
H Cl
CH3 CH3 CH3 CH3
(2S,3R)- (2R,3S)- (S,S)- (R,R)-
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27. * *
2,3-dichlorobutane CH3CHCHCH3
Cl Cl
meso-compound – a compound that has chiral centers but
is not chiral (optically inactive).
CH3
H Cl
CH3
H Cl
CH3
Cl H
CH3
Cl H
CH3
H Cl
CH3
Cl H
CH3
Cl H
CH3
H Cl
I II III
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28. Reactions involving stereoisomers:
(a) the conversion of an achiral molecule into a chiral
molecule, with the generation of a chiral center.
n-butane + Cl2, hv sec-butyl chloride + etc.
achiral chiral
*
CH3CH2CHClCH3
CH3
C2H5
H Cl
CH3
C2H5
Cl H
(S)-(+)-sec-butyl chloride (R)-(-)-sec-butyl chloride
product is optically inactive racemic modification
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29. The synthesis of chiral compounds from achiral reactants
always yields the racemic modification.
Why? ‡ R is enatiomeric to ‡S
Eact (R) = Eact (S)
rate (R) = rate (S)
equimolar amounts
racemic modification
optically inactive
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30. (b) reaction of a chiral molecule where bonds to the chiral
center are not broken.
* *
CH3CH2CHClCH3 + Cl2, hv CH3CH2CHClCH2Cl
+ etc.
A reaction that does not involve the breaking of a bond to a
chiral center proceeds with retention of configuration about the
chiral center.
Can be used to “relate” configurations. If a compound can be
synthesized by such a reaction from a compound of known
configuration, then the configuration is known in the product.
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31. CH3CH2CHCH2OH + HCl
CH3
CH3CH2CHCH2Cl + H2O
CH3
* *
It is known from X-ray crystallography that (-)-2-methyl-1-butanol is the (S)-isomer.
When pure (-)-2-methyl-1-butanol is reacted with HCl, the product is dextrorotatory.
Since no bonds to the chiral center were broken in the reaction, the (+)-1-chloro-2-methyl
butane is now known to be the (S)-isomer.
CH3
C2H5
H CH2OH + HCl
CH3
C2H5
CH2-ClH
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32. (c) reactions like (b) in which a second chiral center is
generated:
* * *
CH3CH2CHClCH3 + Cl2, hv CH3CHClCHClCH3
+ isomers
CH3
CH2
H Cl
CH3
H Cl
CH3
H Cl
CH3
H Cl
CH3
Cl H
CH3
+
(S)- (R,S)- (S,S)-
diastereomers in unequal amounts
The transition states are “diastereomeric”, the Eact’s are not
equal, the rates are different.
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33. (d) reactions of chiral compounds with optically active
reagents.
Enantiomers have the same physical properties and cannot
be separated by normal separation techniques like
distillation, etc.
Enantiomers differ in reaction with optically active reagents.
Enantiomeric acids or bases can be reacted with an optically
active base or acid to form salts that are diastereomers.
Since diastereomers have different physical properties
they can be separated by physical methods. The salts
can then be converted back into the free acids or bases.
Resolution – the separation of enantiomers.
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34. (+)-HA + (-)-Base [(-)-baseH+
,(+)A-
] +
(-)-HA [(-)-baseH+
,(-)A-
]
(enantiomers) (diastereomers, separable)
[(-)-baseH+
,(+)-A-
] + H+
(+)-HA + (-)-baseH+
[(-)-baseH+
,(-)-A-
] + H+
(-)-HA + (-)-baseH+
A racemic modification is converted by optically active
reagents into a mixture of diastereomers which can then be
separated. (resolved)
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35. (e) a reaction of a chiral compound in which a bond to a chiral
center is broken…
In a reaction of a chiral compound in which a bond to a chiral
center is broken, the stereochemistry depends on the
mechanism of the reaction.
CH3CH2CHCH2-Cl + Cl2, hv
CH3
CH3CH2CCH2-Cl + isomers
CH3
Cl* *
(S)-(+)-1-chloro-2-methylbutane racemic-1,2-dichloro-2-methylbutane
optically inactive mixture
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37. In a reaction of a chiral compound in which a bond to a
chiral center is broken, the stereochemistry depends on the
mechanism of the reaction. This means that we can use the
stereochemistry of such a reaction to give us information
about the mechanism for that reaction.
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38. Homework problem 4.24
“Altogether, the free radical chlorination of
(S)-(-)-1-chloro-2-methylbutane gave six
fractions of formula C5H10Cl2. Four fractions
were found to be optically active, and two
fractions optically inactive. Draw structural
formulas for the compounds making up each
fraction. Account in detail for optical activity
or inactivity in each case.”
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40. CH2Cl
H3C H
CH2
CH3
Cl2, hv
CHCl2
H3C H
CH2
CH3
No bonds to the chiral center
are broken, configuration is
retained. Product is optically
active
A
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41. CH2Cl
H3C H
CH2
CH3
Cl2, hv
CH2Cl
H3C Cl
CH2
CH3
A bond is broken to the chiral center.
Stereochemistry depends on the
mechanism. Here, the intermediate
free radical is flat and a racemic
modification is formed. This fraction
is optically inactive.
B
CH2Cl
Cl CH3
CH2
CH3
+
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43. CH2Cl
H3C H
CH2
CH3
Cl2, hv
CH2Cl
H3C H
CH3
No bond is broken to the chiral center
and a new chiral center is formed. The
products are diastereomers and each
fraction is optically active.
D
CH2Cl
H3C H
CH3
+
ClH HCl
E
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44. CH2Cl
H3C H
CH2
CH3
Cl2, hv
CH2Cl
H3C H
CH2
CH2Cl
No bonds to the chiral center
are broken, configuration is
retained. Product is optically
active
F
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45. CH2Cl
H3C H
CH2
CH3
(S)-(-)-1-chloro-2-methylbutane
Cl2, hv CHCl2
H3C H
CH2
CH3
CH2Cl
H3C Cl
CH2
CH3
CH2Cl
Cl CH3
CH2
CH3
CH2Cl
CClH2C H
CH2
CH3
CH2Cl
H3C H
CH3
CH2Cl
H3C H
CH3
CH2Cl
H3C H
CH2
CH2Cl
Cl Cl HH
A B
C D E
F
optically active
optically inactive
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