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Organic Short Notes

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Akshit Rajpal
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0% found this document useful (0 votes)
289 views

Organic Short Notes

Uploaded by

Akshit Rajpal
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
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HaloAlkanes F

Hydrogen atom in
• B.pt Order → R I -

> R Br > R
- -
U >R -

aliphatic hydrocarbons replaced by •


m.pt
of p -
isomer is more than that of
halogen '
ortho and meta due to symmetry .

R ✗ -

( ✗ =F,U,Br,I) .
The density increases with increase in

classification : → 1° R CH,- -


no .

of carbon atoms , halogen atoms and


atomic mass of the halogen atom .

• Haloalkanes -
→ 2
.

R2 -
CH -
✗ •

Solubility Although Halo alkanes, are polar


but they can form
Hydrogen bond
not

Rz C- ✗ hence they are


'

→ 3
-
with water molecule

✗ insoluble in water and soluble in Organic



Allylic Halide i solvents .

CH
,
__ CH -
CH
,
-

✗ Finkelstein Reaction
É R It Nax
And Halide
-

NAI
Halide Vinyl Halide R X +
Benzyl
-


Acetone

"
1- ✗

Swarts Reaction
- R ✗
-
Agf Hgf > (of
, 085b£ R - f-
R ✗ Hao
Preparation
-
+

Yi Properties
r-xcx-Bn.IO
+ Pas
>
R U + HU
Chemical
>
-
+ polls
¥, r ce Best
R OH + so -1114 Method
Elimination Reaction
-
-
-

NaBr.tk#4R-Br-NaHS0u-HaOCHs-qH2*ctf--CtytKU-Ha0
i.

From Alkene
ÉH Mark
¥
.

chap
R
+ HX
-

R cH=ctg
-

,
ce
R -
CH =
ctg-HB.se#EideR-ctg-CH ,
Anti -
Markovnikov's
Acc .
to Saytzeff Rule
Rule
Test of reaction, preferred
1,1=4,1 + By Bray ago, - ( unsaturation )
In elimination
is in which double
alkenes one

c- Atom are more alkylated


ctg-ci-ctg-ctg-cq.ci?
ce
bonded
Halogenation : .

€1> is
ay ay ay is ✗

¥4
- -

major CH CH, CH -
CH - CH CH -

CH (
H2 ] ,
- - -

,
80%
I
Preparation of Haloarenes
D8 CH=CHz
+
Ctf Ctf
- -

[
20%

1- Cao , 2501 AH KOH alcohol


High Polarity



R ✗ -

Alc KOH → Alkene → low Polarity


dark
.
.

¥
"
san¥¥mñ Reaction with Metal
[ ✗
Galtermann r×→ %
R ✗ -
+
Mg II R Mg ✗ - -

÷÷→i¥
" Grignard Reagent

¥1 CH] -
U -1mg #
Ether
CH, -

Grignard Reagent
Mgcl

Physical Properties Grignard reagent are highly reactive


and react with any source of
B. P ✗ Mol Mass
give Hydrocarbons
.

proton to
B. P ✗ Surface Asea

BP ✗
11 Branching
.mn#. . KcN-,RCN+kx
WURTZ REACTION Resonance in Haloarenes :
R ✗
-
+ 2Nd 1- X -
R ¥3 R R -12 Nat
-

\ Aryl Halides are less reactive towards


Nucleophilic substitution reaction because
FITTIG REACTION c- a bond acquire partial double bond

¥ne
due to resonance as a result the bond
✗ + 2Nd -1×-47
cleavage in Haeoasenes is difficult than
WURTZ FITTIG REACTION " halo alkanes
;ii
É¥
: :

R ✗ -
+ 2Nd -1×-5=3 -97% ,
R -


A

Nucleophilic Substitution Reaction :


when an atom or

group of atom is replaced by nucleophile


'

I. E- E- + Noo →
FEE + :X
leaving group .

Sni ( Uni molecular Nucleophilic) SNLC Bimolecular Nucleophilic )


ft ] CH }
^

④ % Br ¥1 -4-1 -0
0µA É ]
CH Bo
[
-

+ -
ce → HO . . .
a
,
t
'
CH CH ]
, H H
H

CH ] FH] H
⑧ e' ¥ →
110¥, + a-
-

+ OH
qµj
CH OH
-

CHTICH ,
,

Reactivity order 372° > 1° Reactivity order 1072730


Polar Photic solvent is used
.

• •
Inversion of Conti . takes blace

Racemisation takes place •
Nucleophile attack from obb side .

Aq, NaOH
, R OH
-
+ KX
µ .
. .. ..
is ortho and
Halo group on benzene ring
para directing due to +R effect
¥1 ,
R -
NC + Agx
KNO '
> R -
ONO + KX
É +

Halogenation
H "" f
§¥q+%N%
-
> R NO, - + Agx cone HMO ]
ie
p ✗
.
-

,
-

É
cone Hzsou
Ntfl HX it
.

R -

É¥
€¥^÷É¥g
""
R COO Ag
-
R COOR -
'
1- Ag ✗ +
,
is Predominantly ionic the attachment
ÉI
,,
KCN ,
CH] U ""

place mainly through carbon atom


¥↳if¥µ
takes -1

and thus foxm cyanide ,

É
É÷,µ
is covalent in nature ctgcou
'" %
Agent
-

+
-1

nitrogen is free to donate the eo ¥16s ,

pair forming isocyanide .

Pasa isomer is the major product


Alcohol ,
Phenol and Ethers
Alcohol phenol Ether HCHO
i
)RMgX
> 1° alcohol
i ;) Hao / µ+
"
R-H+¥R- OH
Iփ R - O - R '

REHO II 2° alcohol
Str . Str . Sits II ) H2O / Ht
eoq
.
. .

" " RM "


% +
TH CH CH R co R -
> 3° Alcohol
Hgf
-

( II )
.

108-9
'
,
111.7
' ,
H2O / H -1
due to double due to
due to Lp Lp Lucas Test ( Lucas Reagent Hq + znqz )
-

bond ÷: haraclex bulky alk "


repulsion
and spa hybridise, 900lb '

1° alcohol 2. alcohol 3
'
alcohol

R
Types of Alcohol R CHA OH -1114
- -
R -
CH -
OH
-1174 R - c- OH -1116
'
h
1° 20 3° Link r
finch
p 1,2mHz
R
city -1µg
R "till
R >CH OH ¥ -1110
-

- CH OH - -
- OH R -
CH -

U -1110 R -

,
R Turbidity k r
R
Ally/ Alcohol Benzyl Alcohol Vinyl Alcohol appears on Turbidity abbeasss Turbidity
( OH heating in 5min appears
H2
.

CHECK OH
-

CH, CH CH CH immediately
-

-
.
-_ - -
OH
, .

Methods of Preparation Preparation of Phenol


U
PNA
CH ] CH + KU 623K 1-
-
U +
aq KOH → -
OH
+ NaOH *
¥ Lot
}
.

Froth Carbonyl Compound Phenol

É
"
É Ha
-Ét CH ] CH
cuz
¥1
H + OH
- -

,
-

É MICH} %!
Ei
" "

¥0
CH CH CH
+
Ha
- -

}
-

}
-

> " •

É
r - -
OH
i¥%÷ R CH.
- -
OH

cymene Process ,CH]


From Alkene :

Acid catalysed
Hydration

, -,cµ
- CH

+0,
,


¥00M
É É%
> c=cµ
"
(
+ Hao Hz -41
Physical Properties
"
on

Hydsoboration -
Oxidation Rxn
Due to
strong hydrogen bonding b/w

ctlz-CH-ctf-CB.tl])z→ @ Hs -

Ctf Ctf)jB -

molecules
of alcohol, they have higher
b.pt compared to molecules

-111dg # 0¥
as of
CH, - CH
,
- OH ? > alkane
having same molecular mass .

From Grignard Reagent : As molecular weight increases


pmgpg also increases and


surface
,
area

H -
% -
H + CH
]MgBr
→ H C
-
-
H -1110¥ there is increase in Van der
EH ,
Waal force As . a Result m.pt
CH ] -

CHZOH + Mg ¥,
increases .
• The b.pt of phenol increases with increase HU
a¥a ↳ Hs -
U + Hao
in no .

of C- atoms .
,

HI

Nature of Phenol : Recep


> ↳ tho -11--2+110

PUS
Ut POU
of acidity ¥-011 > 1° > 2° > 3° > ↳ Hs -1 HU
-

order ,

electron
withdrawing group like NO
-

, , sock
-
✗ -
CHO -

COOH increase acidic > ↳ Hs -


U + so
,
+ HU
, ,

to
strength due -
I effect while
NHS NH
electron donating group like -
R , OR -
> ↳ Hs -

,
+ Hao
2h4
decrease acidic strength due to +I
Na
effect gas.
-

OH -

> ↳ Hs ONA -

Na •

> + H, CH> COOH


, CH COO
,
GHS
NaOH
, + Hao 112504
In 413k
> ↳ Hs -
O -

GH,
y
Distillation , + 2h0

NHS " CHZCHO # CH COOH


,
y
2mHz
+ H2O
11504

µ
CH2=CH, -11120
[☒
Pus ,

yank
> +
tho
- cool C"
> ( 00 t CH CHO + H
, ,
NaOH 573K

Bra
Bry Br
water
,
2.4.6 Tri
-
I2+N%H CHI,
' bromo
By
phenol ✗ idation
É¥Br+
on
Bru
>

es
,
'
1. alcohol Aldehyde
Br
o - and b- Bromo Phenol
20 alcohol ← Ketone
cone HMOs
.

NO NO , NORM
, 30 Alcohol
cone .

Hzsoq
'
NO
, '

2,46 -
Trinitrophenol Ethers R O R
- -

Cn Han -1,0
con " " "

[¥so,H 4¥
;
+ Preparation
99, -

150,11

¥-1
HMOs
Dehydration of Alcohol

No,
> +
,
'
NO
21914--0111 ¥÷ ↳ Hs -
O -

GHS
KOLBE 'S
,
NaOH -10 COOH "" "
; salicylic
Reaction
242µs 6) AGO ↳
H -1
Acid • - + ↳ Hs -0-4115
Reimer Tiemann CHU] -11909 Salicelldehde

|
CHO
-

Rxn
, Williamson synthesis CSNY
HIR
March
-

✗ + Nu O - -
R
'
→ R OR ' - + Max
07
Oxidation Rxn 1° ether will form
,
Benzo quinone •
If alkyl halide is
tfsoy
is Je alkene will form

If alkyl halide
¥
"
""
"
¥
Brain CH , COOH
chemical Properties > c-
" "

!
" " ""

Ethers are less reactive than alcohols Bs


is 08 tho and
Alkoxy ion para PCH,
¥10

%
""" " "

Egg
it activates the
directing benzene
cone .tl
+ ,

sub Sou
ring towards electrophilic .
3 ,

+ NO

←É¥"←i¥¥
OCH

¥
,
] , "
on
,

± ctfu / anhy Alas CH
>
-
,
N ,

ÉÉ%
F. C alkylation
icicles +
I 4-7 '
CH
,

R -
O -
R + HX → R OH -
+ R -

CH
,
-
¥-4 lawn
> AIU,
f. c. Acylation
+ Hx →
E) + R ✗

ÉÉ%0cH
-

i-th
II
,
+
order of reactivity HI > HBR > HA

KOCH ,

Biomolecules
Biomolecules
.

Monosaccharides further classified


'

These are naturally


→ are as

occurring organic compounds present as


Aldoses
essential constituents of living organism
in different cells . Monosaccharide contain aldehyde
group .

e.g Giucose
CARBOHYDRATES
optically active Poklhydro -

ketose
-

Xy aldehyde or ketone or compounds monosaccharides contain ketone


that produce such units fructose
on
group e.g
hydrolysis .

On the Basis of taste


Monosaccharides carbohydrates that can't I
be hydrolysed I 4
further Non Sugar
sugar
-

oligosaccharides :
carbohydrate that yield sweet in taste tasteless
2- 10 Molecule of monosaccharides crystalline Solid Amorphous Solid
e.g sucrose lactose
in
,
Soluble In Water Insoluble
polysaccharides: water
carbohydrates which
e9 Glucose e.g starch
yield large of monosaccharides ,
a no .

Fructose
cellulose
.g
on

starch
hydrolysis
,
.

cellulose
Reducing Sugar COOH
{
which HO
carbohydrate •

,
contain ketone
free aldehyde or
@ HOH ) ,
x (CHOM,
group end reduce f-
ehling Solh and i
HNO
]
1

Totten 's reagent COOH


.
( Heon
Saccharic Acid .

e.g All monosaccharides , maltose


CHO
Non -

Reducing sugar "°


-0¥ É CHI
carbohydrates ( ÉH
I 5 CH -
CH
, , o - -

(
-

GHOHI

,
which do not have free aldehyde , → ,
Metonic ghouls and do not
CHAO
§ -43
or
ctgoiy
-

reduce tokens reagent and fettling


Solh sucrose -15 CH COOH
.

e.g ,

D- L Conti .

GLUCOSE :
Glucose is also known as D -

OH of 5th Carbon
grape sugar optically active in nature on RHS
L OH
of 5th carbon
-

Ñeb° "
# Cothzo
Oh U 'S
Str of Glucose :
qztggo, , -1110
.

,
Glucose .

CHO CHO

+ ( 6111206 H OH
H OH
-

fructose
µo - H HO H
Rxh Of Glucose
-

µ - OH
H OH
- OH
H HO -
H
4110 CHIH

( ( HOH )q ^s CH
,
-

Ctf - CH
,
-
Ctf Ctf Ctf
- -
ctgoµ
I
h -
Hexane D- Glucose c- Glucose
CHZOIH 1
I +
"
'
e=° CHIN OH - ✗-171+1 -

Glucose B- Dct) -
Glucose
HE

*
Glucose
( HOH )& ① HOH) , oxime µ - d- OH HO - d -
H

CHZOH 4112011 H -
OH
HO
H -

-
OH

H
HO -
H

H CN H -
OH


HEO -
c- -
OH
← OH
°
° µ o

"

( ( HOH) , CHIH
OH )& 1 CHIH
I

CHIH CHIH ✗ DG)


-
Glucopyranose B- DC-17 -

Glucose cyanohydrin Glucobyranose


H- CHIH CHOY
[ =o

# Oy #
"
COOH µ
0 OH
B"
( { HOH ) >
( ICHOHI,
É¥oH !¥"¥
'

i
, water
,

CHZOH CHIH
H OH
µ
Gluconicncid
Str of Proteins
Proteins
.
:

proteins axe condensation 1.) Primary Structure :


It simply reveals the sequence
polymers in which monomeric units of amino acids .

are ✗ -
amino acid 2.) Secondary structure :
helix sir maintained by H Bond
amino acid

-
.
-

✗ -
sheet Str when R is small
orp -

pleated .

gooub .

40011 3.) Tertiary Structure :


The folding and superimposition
G H
G
- -

of polypeptide chains shake


forms a compact globular .

termed as tertiary Str .

Ntl stabilised covalent, ionic , H Bond


, It is by -

and disulphide bonds


acid
Pettie when two d- amino are
.

:-
6.) Quaternary Structure : The precise arrangement of
joined together ,
a bebtide is constituents .

C- CO NH ) bond is known as
formed -

On the Basis of Molecular shape


peptide bond .
I

CH ] µ Fibrous Protein Globular Protein

☒ d COOH 1- d- COOH Y
HI
- -
-

' '
n n

IH ] H

§ g- I §
-00 "
HI
- -
-

peptide
Amino Acids
( Contain -
COOH and -
NH, grouts )
I

1-

!
"" "
" " " "" " " " "
.

" " "" " " "" " " "" "

essential Non-essential 9%-00 " prepared by Nucleotide also known as


boy nucleotide
te -4
-
NHL nucleotide contain
a
Not synthesised synthesized
. . .
.

Coote
pentose Nitrogenous *) Phosbhate
*,
sugar * )

by the body by the → Basic Base grouts .

body (Chile MHz Pentose Sugar


-
:
either ribose

g carbon sugar or

ie
.

H -
-
NH ,
Coote deoxy ribose

→ Neutral
( not contain

4th oxygen at
2nd position )

H NH ,
-4 -

COOH
Nitrogenous Base
1

Purine Pyrimidine
twitter ion : when a proton is migrated gym gammy , Thymine
→ Adenine →

to amino group dual ion is formed Uracil


group a guanine

,

and this dual ion is called zwilter ion .

Cytosine
Two H Bonds T)
-
present between A&T
are CA __
while three hydrogen bonds are present between
C & G C CIG)

e-

-1
µ

Structure of amino acids :

R
_ Nig in
TH
COO
-

- -

chigherp )
2
HIN
"

-1
-
-
Coo
-

as anion

twitter ion R
ite
C isoelectric point ) HIN -
-
COOH

as cation C low pH )

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