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JEE-Chemistry Handbook

NUTSHELL REVIEW & PREVIEW OF

ORGANIC NAME REACTIONS

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

Reimer Tiemann Reaction H


O O O H OH H
Cl OH C O
CHCl3
H C
+ CCl2 Cl +
H
KO H
CCl2
OH O
CCl4
C OH
KOH

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

Hofmann Bromoamide Degradation


O O O
Br 2 HO
R C NH 2 R C N Br R C N Br R N C O H2O
R NH 2 +K2 CO 3
KO H
H

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

Meerwein Ponndorfverly reduction Al(O Pr i)3


OH O
Pr iO H

Oppeneuer Oxidation (AlO Bu t)3


O OH
Me 2 C O

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

Benzylic acid rearrangement

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

Clemmensen Reduction Aldehyde & Ketone Zn-Hg/ conc. HCl Alkane

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)

Fittig Reaction Halo benzene Na/ Dry ether Diphenyl

Friedel Craft alkylation +RX Anhydrous AlCl3 Alkyl Benzene

O
Friedel Craft acylation +R C Cl or (RCO)2 O Anhydrous AlCl3 Acyl Benzene

Gattermann aldehyde synthesis C6 H 6 HCN+ HCl +ZnCl2 / H 3 O + Benzaldehyde

Gattermann-Koch reaction C 6 H 6 (CO + HCl) anhy AlCl3 Benzaldehyde

carboxylic acid having halogenated


Hell-Volhard-Zelinksy reaction Br2 / red P
-hydrogen atom carboxylic acid
CH 3 CH 2 N= C=S +HgS
Hoffmann mustard oil reaction primary aliphatic amine + CS 2 HgCl2 /
(black)

Hunsdiecker reaction Ag salt of carboxylic acid Br2 / CCl4 , 80C alkyl or aryl bromide

alkali metal salt of carboxylic alkane, alkene and


Kolbe electrolytic reaction electrolysis
acid alkyne
[(CH 3 )2 CHO]3 Al +
Meerwein - Ponndorf Ketone Secondary alcohol
(CH 3 )2 CHOH

Mendius reaction alkyl or aryl cyanide Na/ C 2 H 5 OH primary amine

H 2 , Pd/ BaSO 4 , S, boiling


Rosenmund reduction acid chloride aldehyde
xylene
Raney Ni/ H 2 ,
Sabatier-Senderens reaction Unsaturated hydrocarbon Alkane
20 030 0C
CuCl/ HCl or CuBr/ HBr or
Sandmeyer reaction C 6 H 5 N 2 Cl CuCN/ KCN, heat
halo or cyanobenzene

Gattermann Reaction C 6 H 5 N 2 + Cl Cu/ Hx(HBr/ HBr/ HBr Halobenzene

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

Stephen reaction alkyl cyanide SnCl2 / HCl Aldehyde

Ullmann reaction Iodobenzene Cu (heat) Diphenyl

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

S. Abbre vi S tarting Nature o f


Name o f Po lyme r Pro pe rtie s Applicatio ns
No atio n Mate rials Po lyme r
I. Po lyo le fins
1. Polyethylene or CH 2 = CH 2 Low density Transparent, Packing material bags,
Polyethene homopolymer moderate tensile insulation for electrical
(branched chain strength, high wires and cables.
growth toughness Buckets, tubes, house
ware pipes, bottles and
toys
2. Polypropylene or CH 3 CH= CH 2 Homopolymer, Harder and Packing of textiles and
Polypropene or linear, chain stronger than foods, liners for bags,
Herculon growth polyethene heat shrinkage wraps,
carpet fibres, ropes,
automobile mouldings,
stronger pipes and
bottles.
3. Polystyrene or Styron C 6 H 5 CH= CH 2 Homopolymer, Transparent Plastic toys, household
linear, chain wares, radio and
growth television bodies,
refrigerator linings.
II. Po lydie ne s
1. Neoprene Cl Homopolymer, Rubber like, a Horses shoe heels,
H 2C CH C CH 2 chain growth superior resistant stoppers.
Chloroprene or to aerial oxidation,
2 -Chloro-1,3-butadiene and oils, gasoline
etc.
2 Buna S SBR or H 2 C CH CH CH 2 Copolymer, Rubber like, a Manufacturer of tyres,
(Styrene- Butadiene, GRS 1,3-butadiene chain growth superior resistant rubber soles, water
and C 6 H 5 CH=CH 2
Rubber) Styrene to aerial oxidation, proof shoes.
and oils, gasoline
etc.
III. Po lyacrylate s
1. Polymethylmethacrylate PMMA CH 3 Homopolymer Hard, transparent, Lenses, light covers,
(Flexiglass Lucite, H 2 C C COOCH 3 excellent light light shades,
Acrylite or Perspex transmission. signboards, transparent
Optical clarity domes, skylights, air
better than glass, craft windows, dentures
takes up colours. and plastic jewellery.
2. Polyethylacrylate H 2 C CH CO OC 2 H 5 Homopolymer Tough, rubber like
product.
3. Polyacrylonitrile or PAN CH 2 = CHCN Homopolymer Hard, horny and Orion, acrilon used for
Orlon high melting making clothes,
materials. carpets, blankets and
preparation of other
polymers.
IV. Po lyhalo fins
1. Polyvinyl chloride PVC CH 2 = CHCl Homopolymer, Pliable (easily (i) Plasticised with
chain growth moulded) polyester polymers
used in rain coats, hand
bags, shower curtains,
fabrics, shoe soles, vinyl
flooring (ii) Good
electrical insulator, (iii)
Hose pipes.
2. Polytetrafluoroethylene, PTFE F2 C= CF2 Homopolymer Flexible and inert (ii) For nonstick utensils
or Teflon to solvents, boiling coating (ii) Making
acids even gaskets, pump
aquaregia, stable packings, valves, seals,
upto 5 9 8 K non lubricated bearings.
3. Polymonochlorotrifluor PCTFE ClFC=CF2 Less resistant to Similar to those of
o-ethylene heat and Teflon.
chemicals due to
presence of
chlorine atoms.

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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

2 Nylon-6 ,1 0 H 2 N(CH 2 )6 NH 2 Copolymer, High tensile (i) Textile fabrics,


H exameth ylene diamin e linear, step strength, carpets, bristles for
and
growth abrasions brushes. (ii)
HOOC(CH 2 )8 COOH
resistant, Substitute of metals
Sebacic acid
somewhat in bearings (iii)
elastic Gears elastic
hosiery.
Mountaineering
ropes, tyre cords,
fabrics.
3. Nylon-6 or Perlon L NH O Homopolymer Mountaineering
, linear ropes, tyre cords,
fabrics.
Caprolactum
Fe rmalde hyde re s ins
1. Phenolformaldehyd Phenol and Copolymer, (i) with low degree
e resin or Bakelite formaldehyde step growth polymerization for
binding glue, wood,
varnishes, lacquers.
(ii) With high
degree
polymerisation for
combs, for mica
table tops, fountain
pen barrels,
electrical goods
(switches and
plugs), gramophone
records.
2. Melamine Melamine and Copolymer, Tough, rubber Non-breakable and
formaldehyde resin formaldehyde step growth like product. non-plastic
crockery.

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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

Give Test Reducing Non Reducing


1. Tollen's Reagent +ve test ve test
2. Fehling Reagent +ve test ve test
3. Benedict Test +ve test ve test
4. Mutarotation Yes No
O

5. Functional Unit C C O C C C
OH OH

O H O H

OH OR
Hemiacetal Acetal

O H O R

OH OR
H emiketal Ketal

6. Example All monossaccaride Dissaccaride : Sucrose


Glucose; fructose, Polysaccaride : starch cellulose
mannose, galactose,
Dissaccaride : maltose; lactose

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

Starch : (Amylose & Amylopectin)


Amylose : (Straight Chain) :

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

1 ,4 -Glyco s idic linkag e

Cellulose : (Straight chain -D-Glucose unit)

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.
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