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Basics of Organic Chemistry B Paaras Thakur @livedailyjee

Organic compounds and meteorites containing organic compounds have been detected in outer space. A meteorite that fell in Australia in 1969 contained 90 different amino acids, 19 of which are found in living organisms on Earth. While this does not prove that life arose in space, it suggests that events in space may have contributed to the emergence of life on Earth.

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Eluri Yadaiah
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0% found this document useful (0 votes)
277 views132 pages

Basics of Organic Chemistry B Paaras Thakur @livedailyjee

Organic compounds and meteorites containing organic compounds have been detected in outer space. A meteorite that fell in Australia in 1969 contained 90 different amino acids, 19 of which are found in living organisms on Earth. While this does not prove that life arose in space, it suggests that events in space may have contributed to the emergence of life on Earth.

Uploaded by

Eluri Yadaiah
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
You are on page 1/ 132

Do we have Alien origin ?

Organic compounds, some of considerable complexity,


are detected in outer space, and meteorites containing
organic compounds have rained down on Earth since it
was formed.

A meteorite that fell near Murchison, Victoria, Australia,


in 1969 was found to contain over 90 different amino
acids, 19 of which are found in living organisms on Earth.
While this does not mean that life arose in outer space, it
does suggest that events in outer space may have
contributed to the emergence of life on Earth.
● ● ●

● ●

● ● ●


15
16
17
18
More Examples of Lewis structures 19
2 Methanol or formaldehyde
I CHIH Methanol Ufo
H H unpaired
O O
fi
a n n
H
H H
between
Makingone bond
Cand O leaves one unpai
me
3 NH Ammonium ion e on each
of CandO
they pairupto form
c

i
f T ii
a second bond

o
one e is removed
from 5 valence e
g N to make it
positive charged
20

4 Ctej Methylanion 6 UfNOz Nitromethane


Unstable
ms
a inning
O
e
ii
n.fi o
i
fg is put onto the C X
H O N has toe
I H octetexceeded
H c N Q
5 Acetate ethanoate ion µ
i Not this
Uycoo

n
l
I
H
Polar Covalent Bonds & Dipoles 1
21
When a covalent bond is formed between atoms of different electronegativity, the bonding pair of electrons is not
shared equally but is attracted towards the more electronegative atom. Such a bond is said to be polarized , or
described as a polar bond, and the charge separation is represented by symbols δ− and δ+ which represent partial
negative and positive charges. Alternatively, we show the direction of bond polarity by an arrow with the
arrowhead pointing toward the negative end and a plus sign on the tail of the arrow at the positive end.

The bond is ionic only when the electronegativity difference is appreciable (typically, >1.8 on the Pauling scale);
otherwise, the bond is covalent.
Bond Dipole Moments 22

Bondpolarities can rangefrom nonpolarcovalent through polarcovalent to totally ionic


eg
0
Ctf Cte Cte MHz Utz OH Utz Cl Uhs N 6
NonPolar Ionic
Increasing Polarity

Polarity of an individual bond is measured as its bond dipole moment µ


µ 8xd S amountofcharge at eitherendofdipole St
SI unit Debye D D distance bw the charges S­eg
H U
k
H 8xd
d
30 Coulombmeters
I Debye 3.34 10
74 If a protonand e 9 1.60 1019c
were 10 m apart the dipole moment wouldbe

µ 8 0 4.60 1019c x loWm 1.60 1029 cm 1.60 10 D 2924 8D


3 34 1030
C N C O c f C y µ c H N H O
0.2213 0.86D 1051 D 1.56D 0.3 D 1.3113 l 53 D
Molecular Dipole Moments 23
rholeculardipolemoment is the dipole moment
of the molecule taken as a whole
Its a good indicator molecule's overall polarity
of
Moleculardipolemoment is the vector sum of individual bond dipolemoments
F
10N forceon similarly 0 IF
eg a up B
1240,11200 1All
this sphere
zero became
3 forces
H
C
H
O c
µ 0
O
p
µ o
If
µ 2 3D Non Polar
loaf 120 10N Vectorsum O polar molecule Molecule Nffjepolate

H F Hisc pH
L c

g hi H Bfd Br
14 0 µ lo9D
Non Polar Polar molecule
Molecule
U y 24
It If It
c
IF U
401 4 at'tU
U
Twopolarbonds Threepolarbonds fourPolarbonds
bothdipolescancel All dipolescancel All dipolescancel
Mr 0 MR_O µr O

Label thepolarbonds in eachmolecule Indicatethe direction


of net dipolecifany
as Clea b Uesufocte a d Br
17dB g e
MAB
Br Bt a
Br
Br 25
H R
a
1 b
o 7 Mr c It
I
s pigsty
1 9
C s f II µ µr O
U Ms cee l
U
s H
Br
Bothdipoles are equal
opposite and cancel
Benzene is a planar molecule each other completely
d
qq.BR and both Br are in the
plane of the benzene ring
Br e Br
Mr_0 Both dipoles cancel each other 11
l
Br
fl
H I Mr
Br I Bothdipolespoint in
Br µ
the same direction
hence add up togive
a resultant dipole
26

Electronegativity allows us to predict the charge distribution in an organic molecule


S s
0
eg I Is I St St S
Cee CEN
St
Ctl OH
S
C C
ayy As
11111
µ H
µLd
The major factor Influencing the E N is the energy of the orbitals that
the atom uses to acceptelectrons As onemoves left to rightacross the periodictable the valence
orbitals become lower in
energy withinthe same period Going down a group atoms get bigger
in size and valence orbitals are higher in energy E N increases as orbital energy decreases
Then He should have the highest E N as it has the lowestenergyvalenceorbitals but He
can't accept any more its a noblegas The atomwith the lowest energyvalence orbitals
e b'coz
that is not a noble gas is F which is the most E N atom
Electrostatic Potential Surfaces Just for your knowledge no need to memorize 27

In a simple molecule like HClCebu showing the polarity with St and 8 is veryeasy
or
However in more complex molecules there will be
manydifferenttypesof bondswithdiffering
degrees of polarity and the overall molecule will reflect the sum ofthese Thesimple St S

symbolism is no longeradequate and we need an alternate way to view the charge distribution
in complexorganic molecules
Example Classify each bond as nonpolar covalent or polar covalent or state that ions are formed. 28
(a) S 𑁋 H (b) P 𑁋
mH (c) C 𑁋
n F (d) C 𑁋
N Cl
M

Example Would a bond between each of the following pairs of atoms be covalent or ionic?
(a) O, H (b) C, F (c) Li, F (d) C, Mg

Example Show the polarity of each of the following covalent bonds by partial charges and by a dipole arrow.
(a) O–H (b) C–O (c) C–Mg (d) B–H
Example Classify each bond as nonpolar covalent or polar covalent or state that ions are formed. 29
(a) S8Wa
𑁋 HSt (b) P 𑁋
m H (c) CSt
𑁋b F S (d) CSt
𑁋
N Cl s
EN of P and H
Polar NonPolar Polar Polar are very close so
covalent covalent covalent covalent
there is hardlyany
Polarityin P H bond
Example Would a bond between each of the following pairs of atoms be covalent or ionic?
(a) O, H (b) C, F (c) Li, F (d) C, Mg
d de de DEI s 1.7
DEN to DEN 1.7 DEN 1.7
Ionic i Polarcovalent
i polarcovalent butstill
Polarcovalent as carbondoesn'tformionicbonds
Example Show the polarity of each of the following covalent bonds by partial charges and by a dipole arrow.
(a) O–H (b) C–O (c) C–Mg (d) B–H

8 St St s s s1 St S
O H C O C Mg B H
Group Electronegativities 30

Its often convenient to consider groups that make up particularportions of a molecule as having
their own electronegativity compatible with Pauling Seale

Group Electronegativity Group Electronegativity

Utz 2.3 CECH 3.3


Ctfu 2.8 CEN 3.3
Cteclz 3.0 MHz 3.4
cuz 3.0 NHI 3.8
Cfg 3.4 Moz 3.4
Ph 3.0 OH 307
Ctectez 3.0
Bonding Patterns & Formal charge 31
Before we start with calculation of formal charge, let’s just understand its importance in chemistry. Suppose you do
a lot of monetary transactions everyday, then how do you keep track of your account balance? You make a ledger.
Formal charge is also like keeping a track of valence electrons of an atom.

We will be studying lots of reactions and their mechanisms in this course and reactions involve movement of
electrons. When electrons are being moved during reactions, we need to keep a track of this in order to understand
the reaction mechanism.
Bonding Patterns & Formal charge 1
32
33
Assign formal charge to C N and O atoms in the following molecules

a te ch b
µj es ay EN d H
pi
H

e te Ye E f teYg y g Uy NEN

BL
34
S1 H O
I 1H
c b
11 o 0
d H og H
1
a He c nµ ye c Cte c N
i
H p
has 3 e
H
T
p
has
n
hlasse HY
has5 e
has e Ue
oo o O
e teach teoc.io
f g cteg.NO N
T T T X has 55
haste hasUe
has 5e

solution
a
G bing.nqe.n.ie d
d
I L de
N has 6 e Se Se
i I formalcharge
Formal charge and Bonding Patterns 35

In organic chemistry we will be dealing with lots simple and complex molecules so its important
of
to have a proper understanding bonding patterns of common atoms like C N and O
of

Dueto 4 valence e C
E
Y
EC c
forms four bonds in
Neutral state
formal charge 0 formal charge I

if c and not t.g.E e.EE E


These arrangements for
A formalcharge 1 are
octet is maintained
wrong as octetofcarbon
is exceeding due to the
unpaired e
Formal charge and Bonding Patterns 36

Due to 5 valence E
N forms 3 bonds
ni hi N
htt N
and keeps one lonepair
of e fc o Fc I

Can't form 5 bonds as

iii I
octet will be exceeded
N These bonding arrangements ensure
and N doesn't have
octet completion
empty d orbitas for that
Re I

Similarly for Oxygen valence 0

o o o 1 1
O O 0 0
g
fC D fc I Fc I
Molecular structure shapes of organic Molecules 37

Molecules have 3Dshapes What dotheylook like Why does a moleculehave a particularshape
The search for these answers led to the development various bondingtheories These theories
of
explained the known structures and also allowed chemists to predict structures
ofnewly
discovered molecules When a predicted structure was shown tobe wrong theory was refined until

it could account for experimental result

Lewis concept concept


of localized e pair bond Coudritexplain the geometry bondangles
stability
V BT Explains formation ofbonds through overlap atomic orbitals
of
vs EPR theory Explains the right arrangement ofbondpairs and tone pairs in space around
central atom to achieve stability

Allows us to modify the atomic orbitals in such a


way to explain
correct
Hybridization
bond angles in molecules Assigns geometry bondangles and bond lengths
VS EPR theory 38

Knowledge
ofmolecularstructures is critical to understanding of their physical chemical
properties Virtually every biochemical process hinges to a great extent on the shapes of
interacting molecules Properties like smell flavour acidity basicity reactivity ele depend on
molecular structure
bondpairs
e pairs mean lonepairs
VSEPR Valence shell e pair repulsion
g
Based on simplefact that e pair repeleachother and want to stay as far awayfrom each
other as possible Electronpairs around central atom arrangethemselves in such a that
way
repulsions are minimum and structure is stable

I
Tetrahedral shapes 39

Y'npitamnesame µ.gl or
5 or
txt
It
z does Pointed towards
you
a Pointed
Pointed amully away fromyou
away 9pointed towards You
fromyou
Tetrahedral is one the most
of
common geometries
you will
study in organic chemistry
Visualize it perfectly

Lewisstructure 3D formula Ball stickModel spacefillingmodel


Tetrahedral and Trigonal planar geometries 40

z e e NH Ammonia

shape Pyramidal
Geometry Tetrahedral

HD Nater Dihydrogenmonoxide
C o 1
Shape Pyramidal
Geometry Tetrahedral

Ehr
Linear Geometry 41

y S

linear

Trigonal
Planar
Geometries
Hy Ethene HCHO Methanol
42

i
P p
Seo 304 p yo Doo
Koryo 6 1
U a
U HO
Nyo HO
Nyo
U U
5092 POU Pce HMOs HN0z
ThionylChloride phosphorylchloride Phosphorous NitricAcid NitrousAcid
trichloride
Tetrahedral Tetrahedral Tetrahedral TrigonalPlanar TrigonalPlanar
Atomic Orbitals and their shapes 43

An orbital of specified energy can bethought ofeither as the space around the nucleus
of an
atom available to an e or as a mathematical formulafrom whichthe probability
offinding
an e at a particular location may be calculated

colours
whythesedifferent

These two colours represent two different phases The phasing is solely a result the mathematical
of
functions describing the orbitals One colour indicates that the function is positive in this
region of space and the other colour indicates it is negative
44

meaning to be given to these phases forinstance the probability of finding


There is no other
an e in the differently phased regions is the same

In atomictheory and quantummechanics an atomic orbital is a mathematicalfunction


which describes the location and wave like behaviour
of an e in an atom

Whatis the difference b w orbital and wavefunction 4


Have function contains all the dynamical info about the e ie its energy coordinates
etc 4 is characterised by 3 quantum numbers n eand m

Havefunction a has all the info about e but when we want to


4µm
locate an e we define its n Land M and then it's called an orbital eg 42,0
is 2s atomic orbital
Valence Bond theory VBT 45
What is a covalent bond, and what characteristic gives it strength? And how can we explain molecular shapes based on the
interactions of atomic orbitals? One very useful approach for answering these questions is based on quantum mechanics
and called valence bond (VB) theory.

A covalent bond is formed whenorbitalsoftwo atoms overlap and a pairof e


occupy the overlap region In the terminology of quantum mechanics overlapof
the two orbitals means their functions are in phase constructiveinterference
VB T assumes that all bonds are localized bonds ie bonding e are fixed b w two
This is actually an invalid assumption combining atoms eg A B
w 2atoms
many atoms bond using delocalized e e which are not fixed b
because

Two other key concepts of VBT were developed later 2 Resonance


2 Orbital Hybridization

For the formationof a bond btw 2 atoms e e


t Repulsiveforces
aeet Attractiveforce Met repulsivetree Aetraceiveforces
Overlapping of Atomic orbitals 46
When two atoms come close to each other, there is
overlapping of atomic orbitals. This overlap may be positive,
negative or zero depending upon the properties of overlapping
of atomic orbitals. The various arrangements of s and p
orbitals resulting in positive, negative and zero overlap are
depicted here.

b w same phases
1 PositiveOverlap Overlap
ie constructive interference
2 Negative overlap Overlapbtw opp phases
ie destructive interference
3 Zero overlap No effective overlap of
orbitals
Natureof Covalent bonds T and IT bonding 47
SigmaBond formed by axial or end toend overlap ofatomicorbitals
Leads to greater overlap b w orbitals and hence is a stronger bond

Is Is

Two Hatoms
Internuclear axis

Overlapping

Overlapping of orbitalstakes placealong the internuclear axis ie Of S orbitals


the axis connecting the nucleiofcombining atoms Greater e
density in o or H H
b w the nuclei
Natureof Covalent bonds r and 1T bonding us

IT Bond formed
by parallel orsideways overlapofatomicorbits
Extentof overlap is less so IT bond is weaker than bond
s orbitals don't form it bonds

881
p
2 lobes
only of each
d orbital are participating
Exampleof pit pit bonding day dry in overlap

If gfgffemanfiutoietibeasueo.es
of each d orbital are
participating in overlap
Example of PIT dit bonding
formation of Ctly molecule as per VBT 4g
A bond is formed between two atoms when both contribute one electroneach
ie At 1B AMB Two half filled orbitals overlap to
1B Dl Dt give a bonded e pair
IS 25
G's configuration 2P
of C ftp
4 f It hasonly 2 halffilledorbitals so it
Es can form only 2 bonds in ground state
C off f
9 9 9 One e is excited from as Ip to
give 4 unpairedorbitals toform 4bonds
t t t t
H H H H 4 halffilledorbitalsof Cand 4H
overlap

Onebond is formed by Is 25 overlap This means that all 4 bonds are not same
threebonds are Is ap overlap 3 are similar and one is different
50

But it's experimentally confirmed that all C H bonds of Ulu are alike
So in situations like this normal VBT is not successfuland we introduce a new concept
called Hybridization

t.TL Mixing
iir
BEBEE
P orbital
EESE
p orbital
EEEEEEEEOEESE.no
orbital
s
EEEEo
3 sp orbitals 2

If I mix 2 bowls rice with 1 bowl dal and dothe cooking I get palace So different orbitals
rice and dal when mixedtogether give a new set of equivalentorbitals Cpulao
Hybridization is the process where orbitals ofslightly differentenergies like s Pd intermix
to generate a new set
of orbitals which are equivalent in energies shapeand size known
as hybrid orbitals
like Pulao in the aboveexample
52

Now let's discuss the formation of Ctly once again


Is 25 2p
c CGS 9 t
ft ft
C CES off f g g g Ones andthree p orbitals mix to generate a new
set of 4 hybrid orbitals sp'sorbitals
Hybridize

off 9 f f f Nowthese are no longer S or


p orbitals but are
sp3 orbitals having similarenergy and shape

1 t t t four hydrogen atoms ready to overlap with 4


Is Is Is Is sp3 orbitals of C atom to give Uty

These 4 sp orbitals axially overlap with Is orbitalsofH to form a tetrahedral arrangement


52

No of hybrid orbitals formed No


of participating orbitals

Hybridization Noof hybridorbitalsformed Geometry Bond angle


Stp sp 2 Linear 180
St Ptp sp2 3 TrigonalPlanar 1200

St p Ptp sp 4 Tetrahedral 109.50

of S character sp sp sp3 As S orbital is closer to thenucleus the


501 33.39 25
greather the soloof a hybrid orbital
Electronegativity sp sp2 sp the lower its energy
the smaller its size
Relative Overlap sp sp sp p higher its Electronegativity
53

Hybrid orbitals undergo better overlap compared to pureatomicorbitals this results in stronger
and more stable bonds
Geometry of a molecule is governed by hybridization
Hybrid orbitals form bonds and not IT bonds

O
S
t A
Be of Sp Hybrid Orbital

t CA t CS D sp2 Hybrid Orbital


S Be Ry

O t CA t CA t A I sp3 Hybrid
s Be Ry B Orbital

As p character increases the hybridorbital becomeslonger


54
Totalenergy ofthe orbitals is not changed by the hybridization and energy each hybrid orbital
of
in a set is the mean of the energies
of constituent Aos
Unhybridized Orbitals
L f
formation of Ethane 55

H H
l I
H c C H
I 1
H H
Hoo

Each C atom hasfour bonds


it needs Usps hybrid orbitals just like Chey

axis
This bond is symmetrical along the internuclear
I
C C Now if I hold one carbon atom fixed and rotate the

µ
the carbonatoms
T T X other it will not affect the overlap b w
bond ie rotation about c c is allowed
hands
formed BY
you can visualize this byholding pen withcaps in your
a
sp3 sp overlap and rotate the pen while keeping the capofpen fixed
formation of Ethane GHG 56
c c
eg This pen can be considered an example of bond here
g
rotate
holdthepenbody the cap to Youdidn't faceany problem ie
Rotation about a single bond is allowed 2
we will use this concept in stereochemistry
H H
12 11
HC Cii OD
µ
H th b eye
H y
Carbon Goo
pear
H n j
what you
see
f or I Hold the front

TH at cartebaornfansdonrobtyategoo

front carbon
formation of Ethene Hy 57

I se be
will
excited
Each Carbonforms 4 bonds to2P
2 bonds C H Require 3
I
is a bond C C JHybrid
orbitals aroundState these 3 orbitals
will form
f it bond c C J Requires 1 p orbital 3 o bonds

bond cloud is above the plane


halfof IT e
it
7 of molecule rest half is below

entire GHy molecule is


in one plane becamethe
shape of sp2 hybridization
is trigonal planar
Noofatoms in sameplane 6
formation of Ethene Hy 58
2porbitals ITbond
t b c

H H H H
c
C
T
e
cu H
f H
H

Overlap oftwosp2hybridorbitals Overlapof two 2p orbitals formsthe C C itbond


forms the C C r bond 5 bonds are in the plane the molecule
of
but ITbond extends above and below the plane
Overlap
of sp2and Is orbital
torms the c H bond ofthe molecule
e density of ITbond is not concentrated on the
axis joining the two nuclei
Because the e density in a 7Tbond is fartherfrom
the two nuclei IT bonds are usually weaker
Restricted Rotationabout IT bond 59
we have already learnt that rotation about bond is allowed Now let's understand what
happens when we try to rotate about a T bond

IT bond is formedby sideways overlap p orbitals ie


of
Rotate As we start rotating by keeping a
f gg got f fixed the overlap blue p orbitals is
destroyed So rotationabout a it bond
is restricted
d d
C Cz Doublebonds are rigid and can't be
twisted
Rotateabout
Neill use this
Fcf bond
of Motagua concept in geometrical
isomerism Sovisualise
bykeeping
one carbonfixed it clearly
60

Does it mean that we can never rotate about it bond

IT bond results from sidewaysoverlapof porbitals When the two porbitals are parallel
the overlap is maximum If one of the carbons is rotated about the c c bond the
900 when there can be no
overlap between P orbitals decreases and becomes zero at
1T bond In other words rotation about the e is a high energy process which
does not take place at normal temperature

What is the meaning of and in the lobes of orbitals

These lobes don't refer to positive or negative charges since bothlobesof an


e cloud orbital must be negatively charged These are the signs
of wave function 4
when two parts of an orbital are separated by a node 4always has oppsigns on
the two sides of the node This also explains why s orbital has only or sign
and not both like p orbitals
formation of Ethyne CsHz Gl
H C C H
y
180
Each carbon forms 4 bonds se be
I CH bond Requires 2
will
excited
I C c f
bond hybridorbitals
2 C C ITbonds Requires 2
P orbitals

4 atoms are linear


Two IT bonds extendout
from the axisof
the linear molecule
Trick for calculating Hybridization 62
1800

1
A TRICK for Hybridization
Calculate no bonds free lonepairs
of
Moreclarity on free lonepairs will comeafter
YYntifgyur.es
nanee so don't worry if youdon't

E 1200
2 v T 1 Free L P 2 sp linear
3 sp2 Trig Planar
4 sp3 Tetrahedral
5 sp3d TBP
109.50
I 6 sp d2 Octahedral
3
This is an easiermethod Detailedtheory is
covered in chemical Bonding topic and dsp2
hybridization is covered in coordination compoun
topic
Trick for calculating Hybridization 63
TRICK for Hybridization
Calculate no bonds free lone pairs
of
Moreclarity on free lonepairs will comeafter
don't
Yeventingthrees.onance so don't worry if you

T Free L P 2 sp linear
3 sp2 Trig Planar
4 sp3 Tetrahedral
5 sp3d TBP
G sp3d2 Octahedral
Calculating Hybridization in organic molecules 64
H H 3 I LP 4
eg q µ c c H c H I
µ c c H N H spz
l H
I µ
f 11
G c 4 to LD 3
20 10 L P
n
sp
2 H

s sp3
i sp2
sp2 O p I 2LP 3 sp2
As 11 sp2 o
I 40 06 5
ay ay ay
Cee
_UL Utz H
attacks P y
dps
Io zLp y
2
Cte Ips Fps U a
i sps
at
Sp Ut
at I Tey t
cha
a
ab ut cha at or
p
U
ausps Ips 2 Vsp thatyaall care sp2
65

0 UF Restallaresp carbons
Cte Utz
µqq
H or
30 0 up
stp3 Slp Isps
sp
i
sp2
dP
Cee iii cee Restallaresps
o
CHP y can
y or Vf
µ Sps
3ot2LP 4 O
i sp3 sp Asp3 o

oteff 08 spa0 To
Vhf
spa
E te or ite o
Sps H sp O
µ 30 0LP S OH
0 1 µ O N
i sp2 0
OH
the odd e isin pure p orbital sped sp2
66
Determine the hybridization around the highlighted atoms in each molecule

as CH CECH b p c Ctf c Utz

Seldane is a major drug forseasonalallergies Relenza is a common antiviral

OH OH O
t
I throat
I Tf
b OH
NH NH fd
Seldane 0 7NH
MHz
Relenza

a Draw all the lonepairs of e in bothstructures


b Which orbitals overlap to form the covalent bonds indicated
by arrows a b c and d
67

as CH CECH b NO
ttbcjcHz c

ctez­jprVsp
pz Ipa Tsp
Ipa

sp3 sp yo
no I ao
Il
spa sp
i
sp sp I sp2 sp2
T.N.ie µµ fd
Seldane O T.N.tl
1.7142
Relenza
68
any atom that possesses it
Place formal charge over in the following structures

a CEC b H CEO c
Q N Q d UtzNH

es t
yO Y
0 Ttb MHz
11 I
I EJ't rub
un
Tan t wane
Il t
off
NH
N
Ctb 0 4 µµTNXNHz
Ctl 2
US A theobromine Melamine
Molecule A contains sp2 Howmany lonepairs in Howmany lonepairs in
and sp carbons theobromine melamine
Solution to Practice Problems 69
0
a CEC b H CEO c N Q d CtlzNHz

0
es
y o.info
t EI

yo Ill O
its ivies
u s I ab Il
X No I
O
IX N
ab Hq II in
X N
NH
Hes Mil t iiiiq
A qq.HN
8 sp2 Uts
Molecule A contains
Lonepairs _8 Lone pairs _6
and 6 sp's carbons
Quick Recap of MOT 70

MOT is very important theory to understand the phenomenon which involve molecular energy
levels Its also based on quantum mechanical model atom and
you must have
covered
of
this in detail during chemical bonding If not then brushup the basicsofMOTand then
getback here

Atomicorbitals Aos combine to give Mos


In phaseinteractions constructive interference
Bonding MO Brno higherenergy
out ofphase destructive interference Antibonding MO ABMO lower energy
orbitals that contain pairof e which are not bonding or antibonding Nonbonding orbital
Axial overlap bond
sideways overlap IT bond
BondingOrbital Antibonding Orbital

of

fo Sigma overlap

Dt

f f f
it overlap

t
Molecular Orbitals 72
According to molecular orbital (MO) theory, when two AOs overlap, they combine to form two new orbitals called
molecular orbitals (MOs), and the electrons from the original AOs are now accommodated in the new MO(s).
Whereas AOs are localized on atoms, MOs are associated with molecules and sometimes extend over a whole
molecule.
The simplest example is the formation of the H–H bond
of a hydrogen molecule (H2 ), which involves the
interaction of the singly occupied 1s AOs of two H atoms.
When the two AOs of equal energy overlap, two MOs are
produced. One is lower in energy than the original AOs,
while the other is higher and the new MO of lower
energy becomes occupied by the two electrons (as per
Aufbau Rule) which were originally in the two AOs.

It is this pair of electrons which constitutes the covalent


bond . The H2 molecule is lower in energy (more stable)
than the two separate H atoms, and the energy
difference, which is liberated as heat, is the bond energy
of the H2 molecule.
Molecular Orbitals 73

why Bonding MO is more stable Because in BMO e density blew the nuclei
is greater which reduces the repulsion b w nuclei and provides
stability
e cloud
btw 2 nuclei
Molecular Orbitals 74

why Antibonding MO are unstable In ABMO the e density b w the two nuclei is zero
and hence repulsion b w the nuclei is maximum This makes the ABMO Unstable
Molecular Orbitals 75

a c
o
y 0
O
In a 1T bond the 2 e
stay in BMO and ABM0
is empty

this empty DBrno will be


used in upcoming chapters
to define concepts like
etc
hyperconjugation in alkene
Bond length and Bond strength 76
As 2 atoms comecloser to form a covalent
bond potentialenergy
of the system
decreases and reaches a minimum Point3
This point represents max stability
lowestenergy and distance b w the
atoms at this point is called Bond
length
atoms comecloser than point3
If
the repulsiveforces b w their e clouds
become stronger than attractiveforces
system becomes unstable This
pushes the two atoms apart towards
point3 again
Bondlengthof
H H
77

4 Bond length 9 as we move down the group as distance b w


the nuclei 4

BondEnergy The strength a covalent bond depends on the


of
magnitude of the attraction b w the nuclei and shared e
The energy required to break the bond a particulartype is
known as bond energyCB E
of
Bored breaking
always requiresenergy its an endothermic process
heat is
9 A BCgs ACgs Big AH se KTImol absorbed
Bond energy

strongerthe bond Greater the B E


Noneed to memorise 78
Average BondEnergies Kamel and bond lengths pm gust for your reference
Bond length and Bond strength 2g
Increasing Bond length BondOrder No bonds b w 2 atoms
of
Bonding e Antibonding e

g yeah c
2
Increasing Bond Strength eg c N c c
B0 _2 BO 3 BO I

As bondorder 9 increases bond length


and bond becomes stronger

All C C don't have some bond length


as hybridization plays an importantrolehe

c sp Clsp3 ClspDtclsp2
eg Utz Utz Us at _Utz
1 53 1.55 Ao 1 Ug 1.52 Ao
same trend we find in c H bondlengths
in the table As
Bond length and Bond strength 80

Asthe soloof carbon 4


H
UtsUta H Ctf_qµ 110pm Cte C H in the hybridization the
f I f I 109PM bond length d
Sp PM
111
spz sp

This again confirms that s electrons are closer to the nucleus


81
82

shorter
sp
f a

shorter
sp 3
Shorter

I
Shorter
sp sp3
Br Br F
as
II b IF C
IT 4 U te U
pc µ CpBr gt p d's c e c
IIH th F
f Y
H F UH H
PolarMolecule Polar Molecule MR 0 PolarMolecule µr O
Polarizability 83
molecules that
a
very important property of youmust havestudied during Rajan's rules in
mical bonding let's have a quick recap ofthis as well
Since e are charged particles
they respond to electricfields In particular e in molecules are
mobile to varying degrees so their positions can shift to different extents when
any external
electric field dueto a charge is nearby
e density has shifted duetothe
a simple representation presence of ve charge nearby This
e g is called polarization ie development of ve
e e of a neutral atom and ve poles
It has a symmetrical St s
distribution e
e e
of Place a e
e charge in the absence e t
cation e
Red recharge ofany external near this e
e
Blue e cloud electricfield atom
PositivePole NegativePole
F
84
So polarization is distortion or shifting of e density due to an electricfield nearby
In the previous example the neutralatomgot polarized by the cation So cation has a polarizing
power and the neutralatom has ability to get polarized ie polarizability
Now its easy to visualise that the size of atom anion is bigthen its outermost e
very if
cloud is far from the nucleus and loosely bound So it has higher tendency to get polarized
ie higher polarizability Whereas in smalleratomsfanions the e cloud is more tightly held
thus making them less polarizable
a dipole is induced in the moleculeadding to
Upon polarization any permanentdipolealready
present
This polarization caused byexternalinfluence is temporary ie as soon as i remove that external
electricfield the atom goes back to original state symmetrical distribution of e cloud
of
85

We define the polarizability of a molecule as the magnitude of the dipoleinduced by one


unit of field gradient
Bigger the size ofatomlanion higherthe polarizability
smaller the cation higher the polarizing power

Atomic Polarizability e
C N S O H F 7 He
1076 loIO O 80 0.66 0.55 0.20 asperCRChandbook

I 7 Br 7 U A
47 3.05 2 18 0.55 polarizability across a period
P s 4 down the group
3 13 2.90
86

Polarizability hasprofound consequences whichyou'll encounter in induced dipole nucleophilicity


etc water is a very polarmolecule However methane is much more polarizable than water
This explains the difference b w polarity and polarizability
H
fo I HR i
o_0
µ
O
H II n
H

St S St S
C E bonds are much more reactivethan C Cl bonds in reactions like Snf and EZ
t t which you will study later
Lesspolar MorePolar
Morepolarizable lesspolarizable

Alkenes arenes with themore E N sp2carbons are lesspolarizablethanalkanes withonly sp3


carbons
Differentmethodsof representing molecularstructures gy
Wecan represent molecularstructuresthroughdifferent ways lewisstructure structuralformula
condensed formula or line angledrawing

Uts
Ues Ut
Uf ut
U
b
CteCte U Ut Ut3 z

te
Carbon
t
H
U
88
Determine the geometry around all second row elements in eachof following compounds 89

a Uy
di Ctb b Ctf Cte OH c MHz d Utz N

Predict the indicated bond angles in each compound


H H
un b les
c Br
les
C Br
a Utz CEC H Clea c Cee
nu nu HH
convert each skeletal structure into a complete structure
showing all C's H's and lonepairs

TI b
I
a c d
µ me
quo
X
e t g h
N.lk
Determine the geometry around all second row elements in eachof following compounds 90

sp2 H
a 116 by Do c
fo d
sp
Ue If Uab
n
I Isps
Maginn
te l n't
N O H
te I
µ
sp sps SP H
sp
Trigonal Planar about Tetrahedral around SP3
Tetrahedral Tetrahedraland
central carbonatom both C andoxygen linear

Predict the indicated bond angles in each compound


1800 H 09.50
as Cees c
A H b
1200
If I
58421200
1800
ay Br Uy fH Br ale angle are
7109.50 Slight
sp2 deviation will be
TrigonalPlanar because
of different
groups
91
Utz
o
OH
a
ctfu b l cuz
c 91 I
de de
92 I µ
Ue cygni H
l ai ab
Utz UI cee

o
O H 0
d 11 I o
ab ii Macey C te e
okayEmme t Utz
Cee H
ai Ig
I lay H
u Hi
o te
g eee 9 h dnue
equine.ie
What orbitals are used to form each bond in the followingmolecules 92
a UtzBelt b W B C Uy O Ctb

Predict the hybridization and


geometry aroundeach highlighted atom

a I b c d
of e
Nate

a Predictthe hybridization and geometryaround each


highlighted atom
b Label 5 polar bonds using St and 8
c Howmany and it bonds does amoxicillinhave

Amoxicillin
g
ay H 1 sp s overlap Cys
I by I sp
2
c H c
Ut
11C B sp3 Utz
µ Bee 2 sp3 sp overlap Ttb c µ bonds s
H c Be ab sp
c O bonds sp3 sp
3 SP s overlap c te bonds are sp3 s
Be H B C bonds are sp2 sp

H H Tetrahedral
y b G H H SP
c O ai d
Haug 8cg
nel care sp
uf cee
H HY c
µ
nee cand 0 I
Tetrahedral H
are sp3 All care sp2 sp
2 Tetrahedral linear
sp Trigonal Planar
e
Till
LF O Ctl
00
sp3 Polarbonds are highlighted in green 94
sp2 a

f sp bonds 46

P I IT bonds 6
2
sp

Esp2
Intermolecular forces 95
Intermolecular between molecules Tries to keep molecules closer
Intramolecular within same molecule 7 Holds atoms together to make a molecule eg

Intermolecularforces AHect the Strength IonicBond covalentBond MetallicBond


physical and chemical properties of KUMM 400 4000 150 1100 75 1000
molecules
eg melting boiling point example Nau Hz Uz Cay Fe Ni
reactivity acidity basicity etc Cary Ctey etc Ag Pt
Physical behavior
of the threestate is
Bondingforces ionic covalent metallic are intramolecular
different because the strength intermere
of
cellar forces differfrom stateto state are much stronger than intermolecular forces b'coz
the e density involved in bonding is veryclosebut in
Ion dipole intermolecular forces thedistance b w the e
density is large
rebond
Dipole dipole
DipoleInduceddipole
Dispersion Londonforces
Intermolecular forces Ion Dipole forces 96

M be attractive or repulsive but repulsiveforces come into playonly when molecules come so close
that their e clouds start overlapping This is why most time when we discuss intermolecular
of
forces they are attractiveforces bp mp
These forcesaffect physical properties molecules
of organic eg boilingpoint meltingpoint solubility
etc
St simplest example there
S
of St
St 8 forces is when we dissolve 8 S
S g St St
t Nacl in water Nat U
g g ions are surrounded by H2O g
St g
s g molecules s S
St
St
St S H2O molecule 8
Attractive forces b w cation Nat U
g Attractive forces b w anion
polarmolecules polarmolecules
97
S
ionic be O
of can through s u
Na
S st
U
g test
solubility water St 0 O H s s1
in easily H
solids
Understood forces
ly si
St
H
O H
H
dipole
ion
Watermolecules polar attract the ions
from the crystal and hydrate savate
them The forces b w water molecules
and ions are won dipole forces
Thetotal energy released during the
interaction water and ions is called
of
the HydrationEnergy
creditsErebor
Mountain
Shutterstock
Dipole Dipoleforces 98

St S St S These are electrostatic interactions b w moleculeswhich


St S
I have permanentdipoles eg Chaz HI MHz HCl etc
oppositely charged ends attractandalign
stronger than London dispersionforces but weakerthan
strength 5 25 KHmol ion ion ion dipoleforces as only partial charges are
involved
A
When oppositely charged ends are aligned the attraction 9 and P E 14
Nonpolarmolecules don't engage in dipole dipole interactions eg coz Cay etc
strong dipole dipoleforces result in higher boiling meltingpoints and also affect other properties

St St St
H S H S H S St S St S St S
eg U U U H U H U H G
µgc µgC µqc
H H H
gg
These forces depend on the magnitude
ofthe molecular dipole moment for compounds of
similar ainolar mass the greater the molecular dipolemoment greater the dipole dipoleforces

Mol wt Uh 46 50.48 44 41
Abusing Uhs o Ue Uy U Cee I H Uy EN
BP K 231 248 249 294 355

Source: chem.libretexts.org
Hydrogen Bond 100

Its a special caseofdipoledipoleforces strongerthan ordinary dipoledipoleforces


It requires H atom bonded to a small highly E N atom specifically 0 N F

S St S St
A H 01h11F B Notany random H can form H bonds Hydrogen which is
T
Hbond already part ofa dipole can participate in tebonding with
S St S St
N O or F
N H O H
S S St S si g S St S S St S g St S
Sf g Sf g
f H N H
S St S St
O H o F H
c Hoo o
H X
O U also has E.nl comparable to N but why it
Nopolarity in this doesn't normally participate in te bonding
bond
High E N and small size of NO F create greater St
charge on their covalently bonded H
lol
Unique propertiesofHydrogen that facilitate this uniqueinteraction are electropositivity smallsize
absenceof inner e shells These properties allow X and D to approach eachother
closely
without experiencing
any severe repulsion X H D

Intramolecular H bonding tebonding that exists within the same molecule


Intermolecular H H bonding that exists between 2 ditt molecules
bonding
H
I
ar
O D 90
µ O Hoo N
e
g Neo F H I 11
o ie Enke no
d
EIl
H H H I
N o
XO H O
O
17 µ
Every water molecule can 0
para nitrophenol
form 4 H bonds
If
Intramolecular H bonding Intermolecular H bonding
102
EHectsofH
bonding
Melting and boilingpoints Boiling Point
H2O H2S L Hase Hate H2O UtzOH 76450 Utz Hf CtbUf F
100C 63C 5C ROOM ROH
HF 77 HU C HBR HI
No H bonding
NHS PHz AsHz SbHz T Y b w ethermolecules
y µ bonds 3 H bonds
permolecule permolecule

Nitze MHz Urea is solid while Uts E Cte acetone is


liquid
Amines are more watersoluble than alcohols
of comparable mol wt bcoz aminesact as a better
donor group in H bonding with water
µ µ H H
qµ R Oy
H bonding 4 viscosity and affects acidity stronger weaker
solubility
Intermolecular forces London Dispersionforces 103

Sofar we've discussed the forces between polar molecules but what about the forces that
operate between non polar molecules
eg noble gases alkanes Uz Br etc
Intermolecular force blue non polar molecules is Londondispersionforces or weak VanDer
Waal's forces
Theseforces are weakest and exist in all substances polar or nonpolar But since
they
are very weak we don't normallymention them in polarsubstances
These forces result from the motion of e so they are present between all particles atoms
Ions and molecules
Atanyinstant e density on one side atom
No inherent polarity of
can be greater than the e
in this atom density on opp
side
But the e in an atom this will create a
are moving randomly all momentary dipole
in the atom and this momentary
the time
dipole will polarize the neighbouringatom
104

This process spreads through all atoms in the sample and weak attractive forces b w these
induced dipole come into action These are dispersionforces or weak V D W forces
St S St S St S
ooo ooo ooo ooo ooo

Nodipole a momentary 9
Adipole
dipole is created is induced
due to randomlymoving in this atom eventually theseatoms
e cloud induce dipole in other
nearby particles

very weak forces and are effective only at low temperature


These are when particles are close
and have less thermal energy to escape from attractiveforces
Londonforces 9 with polarizability ie biggermolecules or the ones with more surface area
have stronger London forces
105

strength of
London dispersion forces Polarizability of the particles
I
depends on no
ofe which is greaterin particle
with highermolar mass

Dispersionforces 9 with mol wt ie Chey Ho L C Hg L CyHo


He L Ne s Ar L Kr L Xe
Fz U Brz L Iz

Exceptforthe forces b w small highlypolarmolecules or blue molecules forming Hbonds the


dispersion force is the dominant intermolecularforce e.g In HCl 85 attraction is dueto
dispersionforces and 15
due to dipoledipoleforces
106

what if two molecules non polar havesame molarmass like isomers

one with greater surface area has greater dispersion forces

n pentane and neo pentane same molar mass


e.g
Branchingi reduces surface area straightchain has greater surface area among
isomers
Neopentane
n pentane
Uts Joab

Hawk ayub f
Utz
bp 36.1 C Utz
GreaterSurfaceArea bp g 5 C
lessersurface area
107
Geckos
How walls
on
stick
Vander Wallsforces
A Gecko's foot has toepadsconsisting of about half a million
setae made keratin Eachofthesefinehairs hashundreds
of
even smaller projections
of
of nanoscale diameterscalledspatulae Credits marimalShutterstock
protruding fromtheir ends
The VanderWaals forees created b w
the spatulae and the surface In the
case
of geckofeet the spatulae are
so small and get so close to the
surface that an attractive VanderWaals
forceofaround 0 UµN develops b w
a singlespatulaand a surface
108
for eachsubstance identify the keyintermolecularforceIs and predictwhichone ofthe pair
has the higher boilingpoint
a MgUz or Pcl3 b CtlNHz Or Uff c UtzOH or Utz H

a
Mga consists
of Mg and U ions held togetherbyionic bonding forces Pcl consists
of
polar molecules so intermolecular dipole dipole forces are present Theforces in Mgelz are
stronger so it should have a higher boiling point
b AGNHz and Uff both consist of polarmolecules ofabout the same molarmass UtsMHz
has N H bonds so it can form H bonds but Utz f can'tform H bonds
Og
would BE or II be expected tohave the higher boilingpoint
Both thesemoleculeshavesame no
of of e but IU has a dipole moment

a Can a molecule havedipolemoment if it has no polarcovalentbonds


b How is it possible for a molecule tohave polar bonds but no dipolemoment
a No b If the various polarbonds are symmetrically placed and their vector sum
is coming out to be zero then the molecule will be non polar eg coz Cay etc

listdown a fewpropertiesof water that originate because of H bonding


ay High m p bp highheat of vaporization lowdensityofice compared to water
highspecificheat makeswater a good coolant etc

Which
of followingmolecules can exhibit H bonding a CtesuezOH b Utz o Utz
110
OH
c ClyNHz d LettsgN e UHH f it 8 CHU h

OH
ctbUfOH UtzNHz as 2 Hare bonded to N CMU and

Although Clea has no H directly bonded to an EN atom but still it shows H bonding
bcoz Hydrogen atom should have ve polarity on it to participate in H bonding This
can also be achieved if c atom is bonded to multiple EM atom as in case of Cetus

U This example shows


St s 1413
eg UTC H O c H bonding blue chloroform Ulcers and
I p ab
Q Hbond acetone

Calculate the max number


of atoms that are planar in the following molecules
a Ctf Utz b Ctfu c Cte Cte Utz d Benzene e Ctf 1 642
H 111
H pFanne
a X c by yBackoftheplane
Hl H pyke H 3patfnns.in
one

F
mn
pnfjrnee7 afonmssanaYepianar H Importance
H
1
H5 H
c 42CIC y d
C
e Ht
G H H H Z
H y o c c H
outofPlane C C C
Hd H
ttI
atoms in c c u s
one plane H c H SH
H b atomsare planar
All 6 carbons and
6 hydrogens are This moleculebelongsto
C C in sameplane Allene family
FRONT

BACK
2
whythe hydrogens on end carbonatoms in uy c Uk are in 1 planes

this C forms 2 In adjacent 1Tbond

TH g IT bonds systems Callenes adjacent


1C C
lµ C C C
ITbonds in 1 planes
µ ie

942 c Ctez
The p orbital overlapping T
q HorizontalPlane
for IT bond is 1 to the verticalPlane
Uj c c cHz
sp2carbonatoms

this figureclearly explains that 21T bonds


Uy C CHz C Utz formed by central Catom have to be in
ay
4
sp d d d
O 1 planes c te bonds are present in the
plane 1 to the 1T e cloud Utzgroups
has 2purep d
orbitalsformaking
pz p2 Py Py are in 1 planes
2 IT bonds
113

Howdoes molecular polarity affect physical properties


of compounds
Molecule having higher polarity

has higher boilingpoint

Greater the intermolecular attractive forces More energy is required to separatethem


More polarity 9 the solubility in polarsolvents He
leads to higher melting a boilingpoint
like dissolves like
less polarity In the solubility in less polar1nonpolar
solvents
114
what typeof intermolecular forces are present in eachcompound

a b
In c
Note d e
ace

which compound in each pair has the higher boilingpoint

OH
a N or
H b
dy or
d
C M
or
7 0 d W or

e koµ or
Iko ay f free or Az
115
a No polarity Dispersionforces b Due to presenceof N
y µ there is some polarity
dipole dipole i Dipole Dipoleforces
c H bonding
Koµ d
Dipole Dipole e Dipole Dipoleforces

a b OH

f
or
Te
compact
h or
K
highersurfacearea lesser q bonding
dispersionforces onlydispersion i Higher b p
greater Dispersionforces forces
higher bp
C dipole dipole higher b p
or d w o
Higher bp Biggermolecule
greater dispersionforces
e koµ or
omg f free or I higher B P
has biggeratom I
Hbonding GreaterBp onlydipoledipole i Greater dispersionforces
Functional Groups in Organic chemistry 116

Most organiccompounds have C c and C H bonds Thesebonds are strong non polar and not
brokeneasily But apartfrom C and H organic compounds sometimes have 0 N S P and
halogens Atoms other than C and H are called Heteroatom
T
different

Cte 692 0 H S di OH di Utz


eog Utz NH Utz Utz Clb ay

what differentiates these molecules


to
structuralfeatures like heteroatoms it bonds carbon chain etc
I
These structural features decide the geometry reactivity physicalpropertiesofmolecules

eg carboxylicacids are acidic due to Coote group


117
Functional
group is a groupofatoms that is responsible for the characteristic physical chemical
properties of the compound In simple words F G decideshow a particular class compounds
of
react
eg Typical reactions of alcohols are due to OH group OH is functional group
carboxylicacids are due to COOHgroup COOH

Onecompound can have more than one f G as well R Functional Group

T T
OH N carbon ReactivePart
µ
tycoon Skeleton
0 OH
11
2
f Br

HO I
CHO
INCOOR
Highlighted groups are AG
Typeof Compound GeneralStructure Example functional Group 118

Alkane R H Uy UtzUes
Alkene
4 4 Uez cH Utz c

Alkyne CEC Hec Cte c c

AlkylHalide R X ay ay Br X Halogroup
X f U Br I

Alcohol R OH cte5UyOH OH CHydroxygroup


Ether RO R Ues O Utz OR Alkoxy group
Amine R NHz UtzMHz MHz aminogroup
RzNH UtzzMH
Ryn G 3N
Thiol R SH Uhs SH SH MercaptoGroup
119
Sulphide R S R Utz Stetz SR alkylthiogroup
0 O O
11 11 11
Aldehyde r C H Uys C H c H

O O
Ketone
11
R C R
11
Cee C cute die carbonylgroup

0 O O
11 11 11
R C OH C
Carboxylicacid cage o te ote carboxy group

0 O O
11 11 11
Esler RC o R Cee C O Ub C o

O O O
11 11 11
R c MHz C C
Amide Utz MHz
Y
O O O
11 11 11
Acidchloride R c a chest a C
u
Typesof carbon and Hydrogen atoms 120
Based on the number carbonatom connected to a particular carbonatom we classify it as
of
primary lo secondary120 tertiary 5 or quaternary Cli

10 or Primary carbon which is bonded to only 2 carbonatom


e.g
d c d C 20 or secondarycarbon 2 which is bonded to
only 2 carbonatoms
1 I 30 or tertiary carbon 2 which is bonded to
c only 3 carbonatoms
10 or Primary 20orsecondary U or Quaternary carbon which is bonded to 4 carbonatoms

C C Uy lo
l f lo Cte lo Gt3 lo
CC CC Ctf Ctl lo I I 20
c c Cc Uf
l
e
l 30 so yes quoth Uy ab
e
5 or Tertiary 61220
40 orQuaternary
1
Utz to
121
Degree of H atom Degreeof Catom to which it is connected

Cle
to 10Hydrogens g
CH 10 Hydrogen 6
CHS Ctf go
µ
20 10 20 Hydrogen 2 Utz de Uf Ctl
20 Hydrogens 2
8 20 30 Hydrogen I
Solubility 122

if the extent towhich a compound called the solute dissolves in a liquid called solvent
ie Pandit dissolve IHT
Like dissolves like ie polarcompoundsdissolve in polarsolvents and nonpolarsolutes in non polar
solvents
Haler Polar solvent as it has polarity can form H bonds
Organicsolvents Mostly are non polar e.g Cay hexane benzene or are weaklypolar
e
g UtzO Ctb
Nacl Oil oil acetone

oil layer
water f water f organicsolvent

Nacl ionic dissolves oil non polar oil non polar


dissolves in
in water bcoz bothare polar doesn't dissolve in water organicsolvent nonpolar
123
students sometimes wonder that
if NaCl hasionic bonding which is strongestthen how come
it dissolves in water so easily and breaks the ionic bonds b w Nat and I
No doubt that ion ion interactions in ionic solid like NaCl are strong but when
added to water each icon is surrounded
by so many water molecules through iondipole
interactions Though these forces ion dipole are weaker there are so
many ofthem
that they compensate for the stronger ionic bonds
S St
St O H
St H StHl
H 1 st
St l 8O H S
H OS s St St O
µ
H h
1 o
H
St
s s St l g1
St 0 O H St H H og
H 1st St l
H l
H H ft
solvation hydration ofcation Solvation hydration of anion
124
Mostorganiccompounds are soluble in organic solvents like dissolveslike Anorganiccompound
is water solubleonly it contains one polarfunctional group Nor 0 containing forevery
if
five carbon atoms it contains

COOH OH Hydrophilic waterloving


waterhating
p
Polarhead
4 Hydrophobic

Non polar polarhead


Nonpolar Hydrophilic can form H bond with water
Hydrophobic Tail
water hating Hydrophobic Carbonchain hydrophobic should not be
verylong
if the substance has to dissolve in water

Cay Soluble
Cay Soluble

Butane
f 110 Insoluble
Acetone
f H2O
Soluble
O 125
11
Acetone has carbons and a polar in functional groups which makes it capable
only 3 of
H bonding with water In fact acetone is so soluble in water that acetone and water
are miscible they form solution in all proportions with each other
s
s1 0 St
H H Utz OH NOH
S OH
o
µ Ls µ bond very
soluble inwater slightlysoluble Insoluble in water
b'coz carbonchain in water as c chain is very
hydrophobic is small as Cchaingetsbigger big
OH
but Khao 04
is
HO boy
note far f we d OH
carbon chain is
Benzoicacid Aceticacid
Glucose bigger but we
have 5 OH groups water Insoluble WaterSoluble
Bigcarbon
chain
the basics of
That's it for
chemistry
organic

but

abhi dost
Picture mere
hai
baaki See u in next book

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