QP CODE: 19002496

MSc DEGREE (CSS) EXAMINATION, NOVEMBER 2019

FIRST SEMESTER (2019 Admissions Onwards)
CH500102 – STRUCTURAL AND MOLECULAR ORGANIC CHEMISTRY
SCHEME OF VALUATION

INSTRUCTIONS TO THE EXAMINERS

⦿ This scheme is only a guideline for valuation. Any other attempt which is equally
valid and correct, may be given due credit.
⦿ Some of the answers given in the scheme are elaborate and this is to help the
examiner in their valuation. Please do not expect all those points in the answers of the
students.
⦿ If the answer is complete full credit may be given even if the required number
of valuation points could not be identified

Part A
(Answer any 8 questions. Each question carries a weight of 1)
(5points –Grade A+; 4points –Grade A; 3 points –Grade B;
2 points –Grade C;1point –Grade D; None-Grade E)

1. What is electromeric effect?

Electromeric effect may be defined as a temperorary effect in which a shared pair of

electrons (pi electrons) is completely transferred from double or triple bond to one of
the atom joined by the bond, at the presence of an attacking reagent. In the case of
multiple bond present between two similar atom, the electromeric shift can take place
in any direction. In the case of multiple bond present between two different atoms, the
electromeric shift can take place in the direction of more electronegative atom.

When a charged reagent approach, pi electrons is completely transferred to oxygen with

the result, oxygen acquires full negative charge and carbon acquires full positive charge.

When the electron displacement of electron pairs are away from an atom or group, it is
+E effect

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When the electron displacement of electron pairs are towards the atom or group, it is -E
effect

(Explanation with or without example: A+)

2. Write a note on the aromaticity of carbon nanotubes

Carbon nanotubes are allotrope of carbon which has unique electrical, mechanical and
other physical properties. Carbon nanotubes are composed of cylindrical graphite
sheets. Both nanotubes and graphite sheets are benzenoid derivatives composed of
sp2 carbon atoms arranged in a hexagonal pattern. Therefore both systems are
aromatic. The extent of the aromatic character of benzenoids can be explained in terms
of the number of possible Kekulé structures

3. How will you prove the alkyl-oxygen cleavaGe in AAL1 type of ester hydrolysis

This mechanism occurs very readily when R’ easily comes off as a stable carbonium
ion.ie when R’ is tertiary alkyl, allyl,benzyl etc. This is the common mechanism for esters
of tertiary alcohols. This mechanism is also known as carbonium ion mechanism. This
mechanism is confirmed by kinetic studies confirmed by O18 labelling and isomerisation
in R’. The Acid hydrolysis of 30 butyl acetate in H2O18yields tertiary butyl alcohol
containing O18 oxygen showing alkyl oxygen cleavage and this supports the AAL1
mechanism.

Secondary and benzylic acetates hydrolyze by the AAC2 mechanism in dilute H 2SO4, but
AAL1 mechanism in con.H2SO4

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Acid hydrolysis of butyl esters results in the formation of isobutylene. Because the
carbonium ion rearranges as shown below. This also supports the AAL1 mechanism

(Mechanism not needed, any two example give full credit)

4. What is Norrish type I reaction?

The bond dissociation energy of a C-C bond adjacent to a carbonyl group is

comparatively small and consequently photochemical excitation of ketone usually
results in the homolytic fission of the α C-C bond. This process of α-cleavage followed
by decarbonylation and intermolecular H-abstraction , finally leads to recombinationis
known as Norrish type I reaction . Both the triplet and singlet state undergo α-cleavage.
in Norrish type I reaction. Example, Norrish reaction of Acetone.

5. Write the R and S configurations of a) glyceraldehydes b) alanine

a)

R glyceraldehyde S glyceraldehyde
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b)

R alanine S alanine

(For three correct structures give A grade)

6. Which structure(s) represents(s) diastereomer of I

Structures II and III are the diastereomers of structure I

7. How NMR can be used as a tool to distinguish enantiotopic molecules

Two hydrogens (or other groups) in an achiral or meso compound that are equivalent
because of a mirror plane are enantiotopic if replacing one of them with a different
group leads to a chiral molecule.

In NMR spectroscopy, enantiotopic protons have the same chemical shift in the vast
majority of situations. However, if they are placed in a chiral environment (e.g. a chiral
solvent (say with an optically active solvent, co-solvent or Lewis acid) then the protons
can become diastereotopic and they will have different chemical shifts. The chemical

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shift difference usually diminishes with distance from a chiral centre, and might even
become zero, but diastereotopic hydrogens are never equivalent. Because
diastereotopic hydrogens have different chemical shifts, they can undergo spin–spin
coupling to each other.

8. Discuss the ring flipping in cyclohexane.

Cyclohexane undergoes a conformational change known as the ring-flip process in

which each axial substituent becomes equatorial and each equatorial becomes axial. The
substituents swap positions because the carbon skeleton undergoes inversion with
respect to a plane slicing through the center of the ring. Those carbon atoms that were
puckered up become puckered down, and vice versa.

Consider the structure 1-methylcyclohexane as our first case, a simple cyclohexane

system with a methyl group as a substituent. In the chair structure on the left the methyl
group is in an axial bonding position but once the ring flip happens, the methyl group
moves to an equatorial bond position. This is an important realization, that if a
substituent is in an axial position in one chair structures it will move to an equatorial
position after the ring flip.

9. SN1 pathway predominates in 20 and 30 alcohols. Explain

SN1 reaction proceeds through a carbocation mechanism. Secondary and tertiary

alcohols undergo SN1 reactions due to the high stability of the carbocation.
Primary alcohols cannot undergo SN1 reactions because primary carbocations are too
unstable to be formed, even when the reaction is heated. Therefore, when a
primary alcohol reacts with a hydrogen halide, it must do so in an SN2 reaction.

Consider the reaction between 2-methyl-2-propanol and HBr.

CH3 CH3 CH3

CH3
5
H3C OH H-Br H3C OH2 H3C
Br- H3C Br
CH3
CH3 CH3 CH3
Substitution
2-methyl-2-propanol Pdt
10. Solvolysis of cis 4-t-butyl cyclohexyl tosylate is much faster than its trans
isomer. Why?

SN1 reaction proceed through the formation of a carbocation. In cis isomer (a,e)the
formation of carbocation is sterically accelerated by an axial substituent. The formation
of carbocation relieve the sterric strain due to 1,3 interaction. Since 1,3 interactions are
absent for trans isomer(e, e) , no sterric acceleration will operate on this configuration.
Therefore cis isomer undergoes solvolysis faster than the trans isomer by a factor of
about 3-4.

Part B
(Answer any 6 questions. Each question carries a weight of 2)
(9 0r 10 points- Grade A+; 7or 8 points –Grade A; 5or 6 points –Grade B; 3or 4 points
–Grade C; 1 or 2 points –Grade D; None –Grade E)

11. Explain the MO picture of butadiene

1,3-Butadiene contains two double bonds that are conjugated. In 1,3-Butadiene the four
carbon atoms are in sp2 hybridised state each contributing a p atomic orbital containing
1 electron. Molecular orbital theory is based on the concept of delocalized pi bonds.
One way of visualizing the conjugation taking place inside a 1,3-diene is by analyzing
the pi-molecular orbitals of the molecule. Another way is to construct the pi-molecular
orbitals of 1,3-butadine by using the molecular orbitals of ethylene. In the first method
the four 2p atomic orbitals combine mathematically to form four pi molecular orbitals of
increasing energy. But the second method requires an in-phase and an out-of-phase
combination for both the π and π* of ethene. By both the method the pi-system of
butadiene will contain 4 pi molecular orbitals. Two among these four are these – the

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bonding MOs which are lower in energy than the others, which are antibonding and are
higher in energy. The π molecular orbitals are of butadiene are represented by ψ1, ψ2,
ψ3,ψ4. Among this ψ2, is HOMO and ψ3 is LUMO. The nodes of these orbitals are
0,1,2,3 respectively.

Π-Molecular orbitals of butadiene from ethene

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12. Predict the product of the reaction and suggest a mechanism

This is SNAr mechanism.

(Product only-D grade)

13. Illustrate with an example , the use of primary isotope effect in the study of
reaction mechanism

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The kinetic isotope effect (KIE) is a phenomenon associated with isotopically
substituted molecules exhibiting different reaction rates. KIEs are invaluable tools for
understanding of reaction kinetics, mechanisms, and solvent effects. Kinetic Isotope
Effects (KIEs) are used to determine reaction mechanisms by determining rate limiting
steps and transition states. KIE expressed as ratio of rates, e.g. KH /KD. Clearest isotope
effect with H and D due to largest mass difference.

Primary kinetic isotope effects are rate changes due to isotopic substitution at a site of
bond breaking in the rate determining step of a reaction. Here bond to isotope is broken
in the reaction. H/D has a large effect and easy to measure. Consider the bromination of
acetone: kinetic studies have been performed that show the rate of this reaction is
independent of the concentration of bromine. To determine the rate determining step
and mechanism of this reaction the substitution of a deuterium for a hydrogen can be
made.

When hydrogen was replaced with deuterium in this reaction a kH/kD of 7 was found.
Therefore the rate determining step is the tautomerization of acetone and involves the
breaking of a C-H bond. Since the breaking of a C-H bond is involved, a substantial
isotope effect is expected.

(Explanation with any one example-give full credit)

14. Discuss Di-pi methane rearrangement

This photochemical rearrangement is given by non-conjuated dienes. Dienes having π-

system separated by an sp3 carbon(1,4 pentadienes). This rearrangement is also given
by 3-phenyl alkenes in which one of the double bond is replaced by benzene ring. It is
also known as Zimmermann rearrangement or Zimmerman Di-π methane
rearrangement. This rearrangement is found in both cyclic and acyclic dienes. Occurs
solely from the singlet state. 1,4 diene isomerise photochemically to form vinyl
cyclopropanes.

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 (Mechanisms with any two examples-give full credit)

15. Distinguish between configurationally and conformational stereoisomers

Configuration is the spatial arrangement of Conformation is the spatial arrangement of

atoms without considering the internal atoms when all the internal forces are
forces acting on the molecule taken into account.

Geometrical and optical isomers are Ecclipsed ,staggered , gauche and anti
examples of configurational isomers conformations are different types of
observed conformations

The rotation around a single bond does The rotation around a single bond give
not give isomers multiple number of isomers

One form of configuration is not converted At room temperatue one form of

into another form conformation is converted into another
form

The position of atoms or groups in a space The position of atoms or groups in a space
is fixed changes

Example: Geometrical isomers of stilbene- Example: conformation of cyclohexane-

cis and trans, optical isomers of lactic acid- chair, boat
d and l

(Four differences with one example-give full credit)

16. Give an account of the optical activity of spiranes and alkylidene cycloalkanes
with suitable examples

The basic requirement for a compound to be optically active is its non–

superimposibility of its mirror image. Although the largest number of known optically
active compounds is optically active due to the presence of chiral carbon atom, some
compounds are also known which do not possess any chiral carbon atom, but on the
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whole their molecules are chiral; hence they are optically active. The compounds
belonging to this group are allenes, alkylidene cycloalkanes, spiro compounds
(spiranes) and properly substituted biphenyls.

Alkylidenes cycloalkanes and spiro compounds: When one or both of the double bonds
in allenes are replaced by one and two rings, the resulting systems are respectively
known as alkylidene cycloalkanes and spiranes.

The spiranes with even rings and different groups at the terminal carbons show optical
acivity and optical isomerism, while the spiranes with odd rings show geometrical
isomerism

Optical activity of Alkylidenes cycloalkane

Optical activity of spirane

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17. Write on the conformations of sucrose and lactose

Conformation of Sucrose

Sucrose is the most important disaccharide with molecular formula C12H22O11. The
chemical structure of sucrose comprises of α form of glucose and β form of fructose

Sucrose is made up of α D-glucose unit and β D-fructose unit linked by α-1,2 glycosidic
bond.

Conformation of Lactose

Lactose is made up of β galactose and α glucose linked by β- 1,4 glycosidic bond.

(Explanation with structures-give full credit, B grade for any one correct answer)

18. Show the stereochemical course of the debromination of threo and meso-1,2-
dibromo-1,2-diphenyl ethane.

The debromination of threo and meso-1,2-dibromo-1,2-diphenyl ethane are

examples of bimolecular elimination reaction(E2). Bimolecular eliminations are highly
stereospecific and occur only when the two groups to eliminated are in the anti-
conformation. E2 eliminations are anti-eliminations, ie, eliminated groups are lost from
the opposite faces of the developing double bonds.

Thus meso-1,2-dibromo-1,2-diphenyl ethane gives trans stilbene and threo 1,2-

dibromo-1,2-diphenyl ethane gives cis stilbene.
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(Explanation with structures-give full credit, B grade for any one correct answer)

Part C
(Answer any 2 questions. Each question carries a weight of 5)
(20 to 25points –Grade A+; 16 to 20 points –Grade A; 11 to 15 points –Grade B; 6 to
10 points –Grade C; 1 to 5 points –Grade D; None –Grade E)

19. Explain Huckels Rule .Write a note on the aromaticity of annulens

Cyclic, planar, conjugated polyenes with uninterrupted cloud of π electrons above and
below the plane of the ring and having (4n+2) π electrons where n=0,1,2,3 …..are
aromatic. For example benzene, it is a perfect example of cyclic planar molecule with
uninterrupted ring of p orbital bearing atoms; 6 electron system (4n+2, n = 1).
Therefore Aromatic.

Monocyclic compounds made up of alternating conjugated double bonds are called

annulenes. Annulenes are named according to a general nomenclature system in
which the number of pi-electrons in an annulene is designated by a number in brackets,
such as[n]-annulene ( Or n is an even number that represents the number of C atoms in
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the ring). For example, according to systematic nomenclature, benzene is a [6]annulene,
while cyclobutadiene is [4]annulene, whereas cyclooctatetraene is an [8]annulene.

Aromaticity in annulenes is also explained by Hückel Rule.Some annulenes are aromatic

(e.g. benzene), but many are not due to nonplanarity or a failure to satisfy the Hückel
Rule.

4 electrons (even number of pairs; 4n, n = 1) Cyclic, planar,

conjugated system, Antiaromatic

cyclic planar molecule with uninterrupted ring of p orbital bearing

atoms; 6 electron system (4n+2, n = 1) Aromatic

8 π electron system; (even number of pairs; 4n, n = 2) Cyclic, conjugated system. If

completely planar, this molecule will become antiaromatic X-ray structure
determination shows that thismolecule has a ‘tub’ conformation in which all atoms are
not in the same plane. 4 C atoms are in the planeand 4 are above that plane as shown in
the figure
below. Thus the structure is not planar and thus, the π electrons are not delocalised. The
molecule is nonaromatic. (Nonaromatic form is more stable than an antiaromatic form)

In [10]-annulene, there is considerable steric interaction between two internal

hydrogens at 1 and 6 positions. Further, a planar form (regular decagon) requires an
o
angle of 144 between carbon atoms which is too large to accommodate in a sp2
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framework.Thus the system prefers a nonplanar conformation and is not aromatic. If
the C1 and C6 in [10]-annulene, is Bridged by a methylene group, then the compound is
o
reasonably planar with all the bond distances in the range of 1.37-1.42A and show
aromaticity.

o
[12]-annulene (4n, n = 3) is antiaromatic and hence is not stable above -50 C. Its
o
dianion (4n+2, n = 3) is however stable up to 30 C and is aromatic

o
Bond lengths in [14]-annulene range from 1.35-1.41A . It is aromatic (except for the
isomers that are not planar). The steric interactions associated with internal hydrogens
can be minimized if C3, C6, C10 and C13 positions are locked using suitable bridging units.

[16]-annulene shows significant bond alteration, characteristic of

o o
a polyene structure (C-C, 1.46A ; C=C, 1.34 A ). It is nonplanar and
is nonaromatic

The cavity in [18]-annulene is sufficiently large and hence the steric interaction
involving internal hydrogens is at minimum. The molecule is free of any significant

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 angle strain, nearly planar, and show aromaticity. Its estimated
resonance energy is 37 kcal/mol, which is in the range as that of
benzene.

(Explanation of only Huckel rule with any one example- C grade ;

Explanation of aromaticity of any four annulenes with Huckel rule- give full credit)

20. A)Describe the Hammett equation, the importance of Hammett parameters

and explain why Hammet equation is a linear free energy relationship?

B) Discuss in detail the power of Hammett plots in deciphering the mechanisms

Qualitative treatment of the effect of structure on reactivity can be explained with a

linear free energy relationship known as Hammet equation. The effect of substituent
group on the chemical reactivity was explained by Hammet. According to Hammet, the
effect of meta and para substituents on the ionization constants of benzoic acid could be
genral prdictions of ionic influences of substituents in a variety of reactions. Hammet
choose ionization of benzoic acid as reference due to

1) A number of substituted C6H5COOH are known to have the substituents in the meta
and para positions.

2) Ionisaton of C6H5COOH can be studied easily by simple methods

3) C6H5COOH more or less have a rigid framework for which he configuration of

reactivity species do not change much during a reaction or steric factors do not interfere
the polar factors of the substituents.

It is due to the steric influences the ortho substituents are not included in these studies

By Hammet equation
log k/k0 = σ ρ
log k- log k0 = σ ρ
where
σ = Substituent constant (The polar and resonance effect were denoted by σ)
ρ = Reaction constant
k= ionization constant of substituted C6H5COOH
k0= ionization constant C6H5COOH

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Since the effect of substituents on the acidity of benzoic acid in meta and para positions
are different, each substituent has two Hammet sigma values, σm and σp. For the same
substituent , these values of σm and σp are different.

σm for OH=+0.12

σp for OH=-0.37

The σ values are usually small and lie in the range -1 to +1 including zero.

For substituents that increases the acidity of benzoic acid, σ is positive (NO2=+0.78) and
for substituents that decreases the acidity of benzoic acid, σ is negative(NH2=-0.66).

The reaction constant ρ is a measure of a sensitivity of the reaction.

Haammet equation shows a linear free energy relationship. Free energy changes ΔG
involved in the reactions are related with equilibrium constants of the reaction.

The relation is ΔG = -RTlnK

= -2.303RTlogK

By Hammet equation
log k/k0 = σ ρ
log k- log k0 = σ ρ
-ΔG/2.303RT +ΔG0/2.303RT= σ ρ

-ΔG= σρ x 2.303RT- ΔG0

For a given reaction under a given set of conditions ρ, R, T and ΔG0 are constant so that
σ is linear with ΔG. Thus the Hammet equation describes the linear relationship
between the steric effects of substituents on some chemical reactions of free energy
change. When ploting log k/k0 along the y-axis and σ along x-axis, Hammet plot is
obtained.

(Give full credit if section A is properly answered)

21. a)Write a note on the important photochemical reactions of

butadiene.b)Describe the photochemistry of vision

a)Conjugated dienes like butadiene undergo photochemical cycloaddition reactions. But

the thermal and photochemical reactions frequently give different cyclic products.
Butadiene provides an excellent example of the differences:

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The photochemical [2 + 2] cycloadditions of butadiene yields the following products,
involving a diradical intermediate.

b)
Vision is a process in which light is absorbed by a pigment in a photoreceptor cell (by a
dye in the eye) and the photochemistry that ensues ultimately produces a transient
electrical signal that is transmitted to the brain and interpreted as a visual image.
Retinol or Vitamin A plays the crucial role in Vision. The wavelength response of eye is
restricted to 400-800nm. The vital part of eye are lens and retina. The retina is made up
of two kinds of light-sensitive (photoreceptor) cells, known as rods and cones. The rods
are the more sensitive and are responsible for vision in dim light. The cones are much
fewer in number than the rods and provide detail and colour vision in good light. The
part of the retina that corresponds to the center of the visual field contains only cones.
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A red pigment called rhodopsin or visual purple is the photosensitive pigment in the rod
cells of the retina. Rhodopsin is made up of a protein called opsin, and the highly
conjugated aldehyde, 11-cis-retinal: 11-cis-retinal is derived bythe oxidation of viamin A
(retinol). Complexation between opsin and 11-cis-retinal takes place by imine formation
btween the primary amino group of the lysine in the side chain of the protein (opsin)
and the aldehyde group of 11-cis-retinal to form rhodopsin. This protein-retinal
complex absorbs light energy of a visible photon and undergoes stereomutation of the

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11-cis C=C to 11-trans C=C. This change in the molecular geometry of retinal separates
its from the protein surface, since the all- trans structure of retinal cannot b sterically
accommodated on the opsin surface. This detachment of the two components of the
complex is called bleaching of rhodopsin and this causes an electrical signal to the brain,
where it is translated into visual image.

The photosensitive pigment in the con cells is called iodopsin. The protein part is
photopsin.The three different kinds of cone cells in man responds to three different
wavelengths. Each contains 11-cis-retinal and photopsin. The photons of these three
wavelengths caus a change in the configuration of the 11-cis form to all-trans form of
retinal in each type of cone cell, causing an electrical signal to the brain which translates
it to the respective colours. The time taken for all these processes are in the picosecond
range.

22. Explain in detail about i) carbon based chiral centers ii)N based chiral centers
iii)S based chiral centers.

The term stereocenter is also used to describe a center that causes stereoisomerism. In
order to be able to exist as a pair of enantiomers, a molecule requires the presence of
a chirality center

A chirality center is characterised by an atom that has four different groups bonded
to it in such a manner that it has a non-superimposable mirror image. Eg: The
enantiomers of 2-chlorobutane

Molecules can (of course) possess more than one chirality center. Such molecules may
or may not be chiral.

a) Carbon-based Chirality Centers

The most prevalent chirality centers in organic chemistry are carbon atoms, which
have four different groups bonded to them.

Examples- Enantiomers of lactic acid, tartaric acid etc.

Chirality Centres other than Carbon

Any atom which has four different groups bonded to it is a chirality center. The more
common of these atoms, with which an organic chemist should be familiar, are N S, and
P (a lone pair is included as one of the four different groups). They may be tetrahedral
molecules or trigonal pyramidal molecules (where a lone pair is included as one of the
four different groups)

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b)Nitrogen-based Chirality Centers

When N is bonded to three different groups and has a lone pair, it is a chiral
center because the N has four different environments, the 4th being the lone pair of
electrons. A tetrahedral nitrogen atom with four different attachments (such as the lone
pair, hydrogen atom, ethyl group, and methyl group) is a stereocenter. Important
nitrogen based chiral centres are as follows.

i) Quarternary ammonium salts

Quaterternary ammonium salts of the type [Nabcd]+X-are found to be optically active.

Assuming that the charge on the N atom has no effect on the configuration of the cation,
the cation may be considered as a 5pt system similar to that of carbon in compounds of
the typeCabde. This similarity is based on the assumption that the four valencies in the
ammonium ion are equivalent and this assumption is well substantiated experimentally
and also theoretically. Hence the 3 possible configurations for the cation [Nabcd]+ are I, II
and III. If the configuration is planar I, then it would not be resolvable, it would be
resolvable if the configuration is pyramidal II or terahdral III.

The first definite resolution of a quartrnary ammonium salt was that of allyl benzyl
methyl phenylammonium iodide by means of + bromocamphorsulphonic acid.This was
the first case of optical activity other than carbon.

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This was followed by the resolution of benzyl ethyl methyl phenyl ammonium iodide.
This resolution was proved that that ammonium is not planar, it is either tetrahedral or
pyramidal.

Another example is ethyl isopropyl methyl phenylammonium salt

ii) Tertiary amine oxides

In tertiary amine oxides, abcNO, the nitrogen atom is joined to four different groups and
on the basis that the configuration is tetrahedral, such compounds should be resolvable.
Meisenheimer resolved ethyl metylphenylamine oxide I and this was then followed by
the

resolution of other amine oxides.

Another example is ethylmethyl-1-naphthyl amine oxide II and Kairolin oxide III

In 30 amine the central atom is bonded to three groups in a pyramidal geometry and
possess lon pair of elecrons. They undergo spontaneous inversion of configuration or
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pyramidal inversion. In pyramidal inversion, there is a transition state in which the
bonds from the central atom are sp2 hybridised and the lone pair has pure p-character.

iii)Amines

If the tertiary amine molecule Nabc is planar, it will be superimpossable on its mirror
image, and therefore cannot be optically active. All attempts to obtain optically active
tertiary amines have failed because of the Umbrella effect.

In the tertiary amine molecule, the N atoms oscillates rapidly right angles above and
below the plane containing the groups a, b and c.

When the N-atom is present at a ring junction, in bridged ring systems,pyramidal

inversion is no longer possible without bond cleavage. With proper substitution the
tricoordinate nitrogen becomes a stable centre of chirality as in Troger’s base.In this
compound the nitrogen is trivalent, but the frequency of oscillation has brought to zero
by having the three valencies of nitrogens part of the ring system.

Troger’s base

Substituted Aziridenes are also opically active.

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c) Sulphur-based Chirality Centres

i) Sulphonium salts

The reaction between ethyl methyl sulphide and bromoacetic acid yields carboxymethyl
ethylmethyl sulphonium bromide. This molecule is not superimpossale on its mirror
image and hence can atleast theoretically exist in two optically active forms.
Experimental evidences supports the optical acivity of this compound.

Ethyl methylphenacyl sulphonium picrate is another optically active sulphonium

compound. Optically active sulphonium sals have been prepare from optically acive
sulphoxides.

ii) Sulphinic esters

Sulphinic esters of the type R1SO2R2 are also optically active sulphur compounds. Ethyl
para toluene sulphinate is an example.

iii) Sulphoxides

Sulphoxides of the type R1SO2R2 have also been resolved .

(Explanation of only one section- C grade ;Explanation of two sections B grade; Proper
Explanation with suitable examples of all sections - give full credit)
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