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Aldol Condensation
O O O O O
+ OH
OH H OH
H C CH 2 H C CH 2 C CH 3 H C CH 2 CH CH 3 H C C C CH 3
H H H
H
Claisen Condensation
O O O O O O O
+
EtO H
H 3 C C OEt EtO C CH 2 C CH 3 EtO C C H 2 C CH 3 H C C C OC 2 H 5
H2
OC 2 H 5 OEt
Perkin Condensation
H H O H
O O
H 3C C ONa
C + HC C C CH 3 C C C OH
O HO O O H
Cinn amic acid
Benzoin Condensation
O O OH
KCN
2 C H EtOH C CH Benzoin
CH3 CH3
DMS O
Wittig Reaction H3C C O + C H2 P Ph 3 H 3 C C C H 2 + Ph 3 P O
OH O O
NaOI
Haloform Reaction H 3 C CH R1 H3C C R1
NaOH
CH 3I+R
1
C ONa
I2
H Cl H Cl OH
CHCl3
R N C R N C R N C Isocyanide
Carbylamine Test KOH
H Cl H Cl
H O O
Kobe's Schimdt Reaction C
O H 12 5 C OH
NaO H major
CO 2 / H+ O
HO C
2 25
OH
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JEE-Chemistry Handbook
NaN 3 O
H3 O
O R C N N N R N C O R NH 2
Curtius Reaction R C Cl
O HONO H3 O
R C NH-NH 2 + R N C O R NH 2
H 3 N-NH 2 H
O O
Lossen Reaction H 2 N-O H Accl H3 O
R C Cl R C N OH R N C O R NH 2
or H +
H
O HN 3
H3O
Schimdt Reaction R C OH H SO R N C O R NH 2
2 4
Cannizzaro reaction
O O O O O O
50% slao +
H C H H 3 C C H C H RDS H C OH+ H C H H C ONa +CH 3 OH
NaO H
H O H H
+ OH O
Bayer villiger oxidation H3C OH
O C H 3 C C O C CF3
O
O F3 C C OO H O
O O C CF 3
C (peracid) F3 C C O
H3C
+ OH
O OH 1 ,2 +
-H + H3C C O
H3C C O H3C C O Ph Shift
Beckmann Rearrangement
R R' R R' O H O
C H 2 SO 4
C + H2 O
:N R' C N R R' C N R R' C N R
N +
OH OH 2 H
[Back (to OH)gr. migrate]
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JEE-Chemistry Handbook
Pinacol Pincolone rearrangement
Cl
+
H + Ph
-H2O Cl C C Cl C C Ph
C C H+
OH O Ph
OH OH
KOH
O
+
C C O C C O C C O C C OK
O
O OH O OH OH
Fries Rearrangement
O
O C CH 3 O
60
H O C CH 3 (P)
AlCl3(Anh)
H O C CH 3
Phenyl 12 0
acetate O (O)
O,P (Hydroxy acetophenone)
Claisen Rearrangement
"If o rtho p o s itio n is blo c ke d"
14
O CH2 CH CH2 14
O H 14 O CH2 CH CH2 O H
2 0 0 C
CH2 CH CH2 H3C CH3
2 0 0 C
CH2 CH CH2
14
Birch Reduction
O
O R(+M) O R C OH COOH
Na/ Na/ Na/
liq. NH 3 ; liq. NH 3 ; liq. NH 3
Na/
R H
R C C R' liq. NH 3 C C Na/ +
R C C H liq. NH 3 R C CNa
H R ;
(Acid-base reaction)
trans
Gabriel Synthesis
O O O O
C NH 3 C KOH C + CH 3-I C
O N H N K N CH 3
C C C C
O O O O
O
H 3O + NH 2 NH 2
C OH
+ CH 5 NH 2 O
C OH C
O NH
+ H 3 C NH 2
NH
C
O
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JEE-Chemistry Handbook
Name Re actant Re age nt Pro duct
N+2 Cl OH NH 2
NaOH (phenol) Azo Dyne (Detection of
Coupling Reaction OH or NH 2 gr)
+ or HCl (Aniline)
.. NaNO 2 + HCl +
Diazotization NH 2 N NCl
0 5C
H
Diels Alder Reaction or
Die ne
H
Die nop hile cyclic addition product
O
Etard reaction H3 C CrO 2 Cl2 / CS 2
H
(Benza ldehyde)
O
Friedel Craft acylation +R C Cl or (RCO)2 O Anhydrous AlCl3 Acyl Benzene
Hunsdiecker reaction Ag salt of carboxylic acid Br2 / CCl4 , 80C alkyl or aryl bromide
benzolytated product
Schotten-Baumann reaction (phenol or aniline or alcohol) NaOH + C 6 H 5 COCl O O
O C CH 3 NH C CH 3
sodium alkoxide or
Williamson synthesis alkyl halide ether
sodium phenoxide
Wurtz-Fittig reaction alkyl halide + aryl halide Na/ dry ether alkyl benzene
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JEE-Chemistry Handbook
A D D I T I O N P O L Y M E R S
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JEE-Chemistry Handbook
CONDENSATION POLYMERS
S. Abbre S tarting Nature o f
Name o f Po lyme r Pro pe rtie s Applicatio ns
No viatio n Mate rials Po lyme r
I. Po lye s te rs
HO CH 2 CH 2 OH
1. Terylene or Dacron Copolymer, Fibre crease For wash and wear
Ethylene glycol or Ethane-1,2-diol
or Mylar step growth, resistant, low fabrics, tyre cords,
linear moisture sea belts and sails.
And
O O content, not
HO C C OH damaged by
Terephthalic acid or pests likes
Benzene-1,4 -dicarboxylic acid
moths.
Glyptal or Alkyl HO CH 2 CH 2 OH Copolymer, Thermoplastic, Paints and lacquers.
2.
Ethylene glycol
resin linear step dissolves in
and
HOOC COOH
growth suitable solvents
and solutions,
on evaporation
Phthalic acid or leaves a tough
Benzene-1 ,2 -dicarboxylic acid but not flexible
film.
II. Po lyamide s
1. Nylon-6 ,6 O O Copolymer,
HO C(CH 2 )4 C OH linear, step
Adipic acid growth
and
H 2 N (CH 2 )6 NH 2
Hexamethylenediamine
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JEE-Chemistry Handbook
CARBOHYDRATES
Polyhydroxy aldehyde or Ketone (cyclic hemiacetal / or hemiacetal or acetal or ketal
Monosaccaride (CnHznOn) : single unit, can't be hydrolysed : Glucose; fructose (by glycosydic linkage)
H3 O
Sucrose H3 O
Glucose + Fructose; maltose 2 Glucose unit
H3 O
Lactose Glucose + Galactose
Polysaccaride : Contain more than monosaccaride units
(C6H10O5)n : Starch & cellulose.
TYPE OF SUGAR
O H O H
OH OR
Hemiacetal Acetal
O H O R
OH OR
H emiketal Ketal
Mutarotation: When either form is placed in solution it slowly form the other via open chain aldehyde
form & gradual change in specific rotation until specific value is reached.
6
H2C OH H H2C OH
H 5 O OH H O H H O H
H H
O
H C
4 1 OH OH H
OH H
OH 3 H OH OH OH
2
H OH H OH H OH
-D-Glucose
-D-Glucose []0 = 52.1
[]D=+112
[]D=+19
Anomer's : Difter in configuration at 1st carbon due to hemi (acetal or ketal) ring formation. The new-
symmetric carbon is referred to as Anomeic carbon.
Epimer's : Distereomer's which differ in conformation at one chiral carbon [maltose & glucose (epimers
carbon is C2]
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JEE-Chemistry Handbook
Sucrose : Maltose
OH H 2 C OH H 2 C OH
O H O CH2OH O H H O H
H H
H O H H
OH OH H OH H OH H
OH C H2 H OH O OH
:
H H OH H OH Glycosidic
H OH
-D -Fructo se (un it) lin kage
-D -G luco se
G lyco sidic lin ka ge Tw o a -D -Gluco s e unit
H 2 C OH H 2 C OH
O H H O H H O H
H 1 H
O 2 4 1
OH H OH H
O O O
H OH H OH
(-1 ,4 Glyco s idic linkag e )
(i) Soluble in H2O & give blue colour with I2 (ii) 10 to 20%
Amylopectin (Branch chain) : (C6H12O5)n
H 2 C OH H 2 C OH
(C 6 H 1 2 O 5 )n
H O H H O H
nH 2 O Diatase
H H
4 1 C 1 2 H 2 2 O 1 1 (maltose)
OH H OH H
O O O nH 2 O maltose
H OH OH O 2C 6 H 1 2 O 6 -D-Glucose
H
1 ,6 -Glyco s idic linkag e
CH 2 Cellulose
O H H O nH 2 O Cellulose
nC 6 H 1 2 O 6
O -D-Glucose
n
H 2 C OH H OH
O H 2 C OH
H O
O H H
H OH H O
1 H H
OH H OH
O OH H
H H O O
H
H OH CH 2 OH O
H OH
(-1 , 4 -Gluco s idic linkage )
COOH
Br2
N NH Ph (CH OH)4
H2O
H2C (CH OH)3 C CH N Gluconic acid
Ph NH NH2 CHO CH2 OH
OH (osazone) NH Ph Conc.
3 (CH OH)4 HOOC (CH OH)4 COOH
(same osazone for fructose) HNO3
Saccaric acid
AcO CH2 (CH O AC)4 CHO CH2 OH HI/
red P+
H3C (CH2)4 CH3
Glucose
OH Sarbitol OH
H2O
CH2 (CH OH)4 CH2
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JEE-Chemistry Handbook
AMINO ACIDS STRUCTURE OF
CH 3 PROTEINS
Primary structure : The
H 3 N+ CH 2 COO H 3 N+ CHCOO
Glycine
sequence in which various
-Alanine
amino acids are arranged in a
Thre e protein is known as the
Name o f amino primary structure of a protein.
S .No . S tructure o f R le tte r
acid The number, sequence and
s ymbo l
identity of amino acids in a
1. Glycine H Gly
protein constitute primary
2 Alanine CH 3 Ala structure of a protein.
3. Valine CH(CH 3 )2 Val Secondary structure : The
4. Leucine CHCH(CH 3 )2 Leu coiling of the long strings of
CH CH 2 CH 3 amino acids in a protein is its
5. Isoleucine Ile secondary structure. The -
CH 3 helix is a common secondary
(CH 2 )3 NH C NH 2 structure. In -helix, the
6. Arginine Arg peptide chain coils and the
NH
turns of the coil are held
7. Lysine (CH 2 )4 NH 2 Lys
together by hydrogen bonds.
8. Glutamic acid CH 2 CH 2 COOH Glu Another type of secondary
9. Aspartic acid CH 2 COOH Asp structure is possible in which
10. Glutamine CH 2 CH 2 CONH 2 Gln the protein chains are
11. Asparagine CH 2 CONH 2 Asn stretched out. It is a -pleated
12. Threonine CHOH.CH 3 Thr sheet structure.
13. Serine CH 2 OH Ser Tertiary structure : The
folding and binding of a-helix
14. Cysteine CH 2 SH Cys
into more complex shapes
15. Methoionine CH 2 CH 2 SCH 3 Met
illustratesthetertiarystructure
16. Phenylalanine CH 2 C 6 H 5 Phe of proteins. At normal pH and
17. Tyrosine CH 2 C 6 H 4 OH (p) Tyr temperature, each protein will
CH 2 take the energetically most
18. Tryptophan Trp stable shape. This shape is
NH specific to a given amino acids
which form proteins.
CH 2
Quaternary protein
19. Histidine NH His structure results when
N several protein molecules are
H bonded together to form a still
HN COOH larger units.
20. Proline Pro
COLOUR TESTS
Biuret Test : Proteins give a
violet or blue colour with 10%
ISOELECTRONIC POINT
NaOH solution and a drop of
In electric field these ions will migrate towards the electrodes of opposite very dilute copper sulphate.
charge (+ve ions towards cathode and -ve ions towards anode). At a The test is due to CONH]
certain pH the dipolar ion exists as neutral ion and does not migrate group and is given by all
to either electrodes. This pH is known as isoelectric point of amino compounds containing this
acids. For neutral amino acids. group.
Millon's Test : Millon's
PEPTIDES reagent is a solution of
Condensation products of two or more molecules of -amino acids is mercuric and mercurous
called peptides. nitrate in nitric acid. Protein,
Peptide Linkage : Linkage which unites the -amino acid molecules when warmed with Millon's
together is called peptide linkage. It is CONH linkage. reagent, gives a white
precipitate which changes to
red.
75