Chemistry Handbook CHAPTER - 1

Functional Group Structur Prefix Suffix

e
Carboxylic acid O Carboxy -oic acid
The order of priority of functional groups used in IUPAC nomenclature of Organic compounds

-C-OH
Sulphonic acid -SO3H Sulpho Sulphonic
acid
Anhydride O x oic-
-C anhydride
-C
O
Ester O Alkoxy carbonyl or alkyl…oat
-C-OR Carbalkoxy e
TABLE FOR IUPAC NOMENCLATURE

Acid chloride O Chloroformyl or -oyl

-C-Cl Chlorocarbonyl chloride
Acid amide O Carbamoyl/Amid -amide
-C-NH2 o
Carbonitrile/Cyanid -C N Cyano nitrile
e
Aldehyde O Formyl or Oxo -al
-C-H
Ketone O Keto or oxo -one
-C-
Alcohol -OH Hydroxy -ol
Thio alcohol -SH Mercapto Thiol
Amine -NH2 Amino amine
Ether -O-R Alkoxy -
Oxirane -C - C- Epoxy -
O
Nitro derivative -NO2 Nitro -
Nitroso derivative -NO Nitroso -
Halide -X Halo -
Double bond C=C - ene
Triple bond C C - yne

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CHAPTER – 2

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CHAPTER – 2

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CONFORMATIONAL ISOMERISM
The different arrangement of atoms in space that
results from the carbon- carbon single bond free
rotation by 0-360o are called conformations or
conformational isomers or rotational isomers and this
phenomenon is called conformational isomerism.  Conformations of butane:

Newmann projection : Here two carbon atoms

forming the σ bond are represented one by circle and
other by centre of the circle. Circle represents rear side
C and its centre represents front side carbon. The C –
H bonds of front carbon are depicted from the centre
of the circle while C – H bond f the back carbon are
drawn from the circumference of the circle.

Fully eclipsed Gauche Partially Eclipsed AntiStaggered-form

(Less stable) (more stable) form (most stable)

 The order of stability of conformations of n-butane.

Anti staggered>Gauche>Partially eclipsed >Fully eclipsed

 Relative stability of various conformation of cyclohexane is

Chair > twist boat > boat > half chair

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CHAPTER – 3

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CHAPTER – 4
PRACTICAL ORGANIC CHEMISTRY

QUANTITATIVE ANALYSIS OF ORGANIC COMPOUNDS

ESTIMATION OF NITROGEN

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CHAPTER – 5
DISTINCTION BETWEEN PAIRS OF COMPOUNDS
UNSATURATION TEST DISTINCTION BETWEEN 10, 20 AND 30 ALCOHOLS

TEST FOR TERMINAL ALKYNE

CARBONLY GROUP

NATURE OF X-GROUP IN C-X BOND

If X is Cl, precipitate will be white and for Br yellow

precipitate will be obtained.

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CHAPTER – 5
ALDEHYDE GROUP Chloroethane and chlorobenzene

Chlorocyclohexane and chlorobenzene

Chloroethane and bromoethane

AROMATIC ALDEHYDE GROUP

Benzyl chloride and chlorobenzene

CARBOXYLIC GROUP
Carboxylic acid + Sodium bicarbonate effervescence
RCOOH + NaHCO3 RCOONa + H2O + CO2
Ethyl chloride and vinyl chloride
FORMIC ACID

AMINES 10

n-Propyl alcohol and iso-propyl alcohol

Amine (10, 20& 30 ) (Hinsberg’s test)

Note: Benzenesulphonyl chloride is called Hinsberg’s reagent.

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CHAPTER – 5
Ethyl alcohol and methyl alcohol (Iodoform test) Propanal and propanone(Tollen’s and fehling reagent

Ethyl alcohol and acetone (2,4-DNP)

Phenol and ethyl alcohol(Neutral FeCl3 )

Pentan-2-one and pentan-3-one(Iodoform test)

Benzoic acid and phenol(NaHCO3)

Propanone and propanol (2,4 – DNP) Propanal and benzaldehyde(Fehling’s solution)

Methanoic acid and ethanoic acid (Tollen’s & Fehling

Ethanol and propanal ( Iodoform test) solution)

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CHAPTER – 5
Ethanal and methanal (Iodoform test) Aniline and ethyl amine Diazotisation

Acetophenone and Benzophenone ( Iodoform

test)

Aniline and N-methylaniline (Isocyanide test)

Benzoic acid and Ethylbenzoate

Aniline and Benzylamine(Diazotisation +
phenol)

Benzaldehyde and acetophenone (Tollen’s

test)

Methyl amine and Di-methyl amine

(Isocyanide test)

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CHAPTER – 6

HYDROCARBON-ALKANE
PREPARATION

CH4
CH3-CH3
R-CH2-CH3
CH3-CH2-CH3

REACTIONS

CH4
CH3-CH3
R-CH2-CH3
CH3-CH2-CH3

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CHAPTER – 6

HYDROCARBON-ALKENE

 Order Of Reactivity of Olefins for hydrogenation CH2=CH2 > R-CH=CH2 ( Reverse of stability)

 Order of Reactivity of alkene towards hydration > CH3-CH=CH2 > CH2=CH2

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CHAPTER – 6

HYDROCARBON-ALKYNE
Preparation
Elimination

REACTION

Oxidation

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CHAPTER – 6

HYDROCARBON-BENZENE
PREPARATION

BENZENE

REACTIONS
Electrophilic Substitution Reaction

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CHAPTER – 7

HALOALKANE
PCl5 NaBr + H2SO4

PCl3 HI /KI/H3PO4

Red P + Br2 NBS

CCl4
SOCl2
Cl2/hv
PREPARATION

HBr
CCl4
Nal
Acetone

AgF or Hg2F2
REACTIONS

Physical Properties: (1) Dipole moment : CH3-Cl > CH3-F > CH3-Br>CH3-I (2)Bond enthalpies: CH3-F> CH3-Cl> CH3-Br> CH3-I
(3) Boiling point: R-I > R-Br > R-Cl > R-F (4) Density : n-C3H7Cl < n-C3H7Br < n-C3H7I (5) Solubility Slightly soluble in water

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CHAPTER – 7

TRI-HALO ALKANE
PREPARATION

REACTIONS

Reactivity Boiling Melting

(i) < < <

(i) > > > > >

(ii) < < (ii) > >

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CHAPTER – 7

GRIGNARD REAGENT
REACTION

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CHAPTER – 8

ALCOHOL

 Solubility of alcohol increase with increase in branching n< iso < neo (isomeric)
 Relative order of reactivity
(i) 10 > 20 > 30 (O-H bond fission) (ii) 30 > 20 > 10 (C-O bond fission (iii) 30>20>10 (Dehydration)

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CHAPTER – 8

ALCOHOL

Acid Base Reaction

NSR

CH3-CH2-OH

NSR

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CHAPTER – 8

ETHER

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CHAPTER – 8

PHENOL

REACTION DUE TO BENZENE RING

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CHAPTER – 8

Order of reactivity of
Alkyl Halide towards
SN1 ∝ Benzylic > Allylic > 30 >20 > 10
SN1 ∝ Stability of carbocation
SN2 ∝ 10 > 20 > 30

1
SN2 ∝
Steric hindrance

Reactivity order towards

SN1 or SN2 and E1 or E2
R-I > R-Br > R-Cl > R-F
With increase in number of strong
electron
Withdrawing group at ortho and para
position, reactivity of X towards
aromatic nucleophilic substitution
increase.

< < <

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CHAPTER – 8

Preparation of Aldehyde & Ketone both

Preparation of Aldehyde only

Preparation of Ketone only

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CHAPTER – 8

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CHAPTER – 9

CARBOXYLIC ACID

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CHAPTER – 10

AMINES

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CHAPTER – 10

ANILINE

REACTIONS

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CHAPTER – 10

BENZENE DIAZONIUM CHLORIDE

Gatterman reaction
Coupling reaction

Sandmeyer reaction

FrSR Free Radical Substitution reaction

ESR Electrophilic Substitution reaction
NSR Nucleophilic Substitution reaction
SNAE Subtitution Nucleophilic (addition elimination)
FrAR Free radical addition reaction
NAR Nucleophilic addition reaction
EAR Electrophilic addition reaction
FrER Free Radical Elimination reaction

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CHAPTER – 11
Nutshell review & preview of
ORGANIC REAGENTS
1. Alcoholic KOH 10. CCl4 + OH- (Reimer Tiemann)
R-X Alkene ; Elimination
2. Aluminium Ethoxide

11. CO + HCl + AlCl3

3. Aqueous KOH/NaOH
R-X ROH
Nucleophilic substitution reaction also used for
Cannizzaro reaction with aldehyde.
4. Baeyer’s Reagent (Alkaline cold dilute KMnO4)
12. HCN + HCl + AlCl3
Gatterman Aldehyde Synthesis
13. CHCl3 + KOH

5. Bromine water
(i) Used to detect unsaturation; (i)
(ii)
RNH2 RNC(Carbyl amine
reaction)
(used to detect 10
Amine)(Isocyanide test)
14. CO2 + OH-(high temp. + Pressure)
(ii)
6. Benedict’s solution
Used to detect aldehyde group RCHO RCO2
[Ketone gives –ve test]
7. Cu2Cl2 + NH4OH
Used to detect Terminal Alkyne 15. Cu/
Red Precipitate observed (i) RCH2OH RCHO
8. CrO2Cl2 (ii) R2CHOH R2C=O

(iii)
16. 2,4 – D.N.P.
Used to detect carbonyl
9. CrO3 group(orange ppt observed)
(i) RCH2OH RCHO 17. DMSO
(ii) R2CHOH R2C=O Polar aprotic solvent: favour SN2
(iii) R3COH no reaction mechanism

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18. Fe + Br2/FeBr3 28. H2(Ni) can reduce

19. Fehling solution

Used to identify - CH=O group.
PhCHO gives –ve test
Observation : red ppt of Cu2O formed
20. Grignard Reagent 29. H2(Pd/BaSO4)
Follow (i) Acid base reaction (ii) NAR (iii) Quinoline
NSR
21. H2(Pd/CaCO3) Quinoline (Lindlar catalyst)
(cis)
30. Jones Reagent(CrO3 + dil. H2SO4 +acetone)
22. H3PO2
(i) RCH2OH RCH=O
(ii) R2CHOH R2C=O
31. KHSO4 Dehydrating Reagetn

23. HN3 + H2SO4

32. K2Cr2O7/H
(i)RCH2OH RCO2H (ii) R2CHOH R2C=O
33. MnO2
24. H3PO4/
H3PO4 same as H2SO4/
25. H2SO4/ To oxidize allylic/benzylic hydroxyl group
into corresponding carbonyl
34. NaHCO3

26. HNO2(NaNO2 + HCl)

35. NaHSO3
(i) RNH2 R-OH;
(ii) PhNH2 PhN2 (0-50C)
(iii) PhNH2 PhOH(high temperature)
[White crystal, soluble in water used to separate
carbonyl from noncarbonyl compound]
36. NaOH(aq)
(i) R-X R-OH

(iv)
27. HIO4(Periodic acid)
(ii)

(iii)

(iv)

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37. Ninhydrin 48. Na in Liq. NH3[Birch reduction]

Detection of amino acid
Observation : Purple coloured ion
38. NaOR
Strong base:
49. OsO4 + H2O

(i)
50. O3:

51. Oxirane followed by H+

(ii)
39. NaOH + X2 or NaOX RMgX RCH2-CH2-OH
52. PCC
(i) RCH2OH RCHO,
(i) (ii) R2CHOH R2C=O
(iii) R3COH no reaction
(mild oxidizing reagent)
53. P(red) + Br2
(ii)

40. NaOH + CaO

RCO2H RH (i)
0
(ii) ROH R-Br
41. MnO/ 300 C
Used for –CO2 & -H2O in carboxylic acid. 54. P(red) + HI
42. NBS CH3CO2H CH3-CH3
CH3CH=O CH3-CH3
CH3CH2OH CH3-CH3
(strong reducing agent can reduce any
(i) oxygen or halogen containing compound to
alkane)
43. NaNO2 + HCl 55. Perbenzoic acid[Baeyer villager
RNH2 R-OH Oxidation]
44. NaNH2 in paraffin
Non- terminal Alkyne Terminal Alkyne
(2-Butyne 1-butyne) R’ having more migrating tendency than R
45. Na/EtOH 56. RCI + AlCl3[Friedel craft alkylation]
Reduce all except c/c double & triple bond
46. Zn(Hg) + HCl [ Clemmensen’s reduction]

57. RCOCl + AlCl3[Friedel craft alkylation]

47. NH2 –NH2/OH- [Wolf Kishner reduction]
R-CO-R R-CH2-R

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58. 64. Tollens Reagent Test

(i) Terminal alkyne gives
(ii) Aldehyde Group gives
(iii) Ketone gives –ve test
(iv) α-hydroxy ketone gives
59. SnCl2 + HCl (v) HCOOH gives
(i) R-N=N-R’ RNH2 + R’NH2
(vi) Hemi acetal gives
(vii) PhNH-OH gives
65. Benzene sulphonyl chloride
(ii) It is used to distinguish and
(iii)
RCN R-CH=O [Stephen separate(Hinsberg reagent)
reduction] 10, 20 and 30 amines.
60. Sn + HCl 66. Tetra ethyl lead (TEL)
Used as antiknock compound
67. V2O5
(i)
(ii) RCN R-CH2NH2
61. Silver salt RCOOAg[Hunsdiecker reaction]
Br2/CCl4/ RBr + CO2 + AgBr

62. AgOH/moist Ag2O; (i)

63. SOCl2

(ii)
IMPORTANT NOTES

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CHAPTER – 12
Nutshell review & preview of
ORGANIC NAME REACTIONS
Aldol
Condensation

Claisen
Condensation

Perkin
Condensation

Benzoin
Condensation

Haloform
Reaction

Carbylamine
Test

Reimer
Tiemman
reaction

Kolbe’s
Schimdt
reaction

Hoffmann
Bromamide
Degradation
Curtius
Reaction

Schimdt
Reaction

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Cannizzaro
reaction

Bayer villager
oxidation

Cumene

Pinacol-
Pincolone
rearrangemen
t

Birch
reduction

Gabriel
Synthesis

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NAME REACTIONS
Name Reactant Reagent Product
Clemmensen Aldehyde & Ketone Zn-Hg/conc.HCl Alkane
Reduction
Coupling NaOH(phenol) Azo Dye
Reaction HCl(Aniline) (Detection of OH or
NH2 gr)

Diazotization NaNO2 + HCl

00-50C
Etard reaction CrO2Cl2/CS2

Fitting reaction Halo benzene Na/Dry ether Diphenyl

Friedel Craft Anhydrous AlCl3 Alkyl Benzene

alkylation + R-X

Friedel Craft Anhydrous AlCl3 Acyl Benzene

alkylation

Gattermann C6H6 HCN + Benzaldehyde

aldehyde HCl/ZnCL2/H3O+
synthesis
Gattermann- C6H6 (CO+HCl) Anhy AlCl3 Benzaldehyde
Koch reaction
Hell-Volhard- Carboxylic acid having α- Br2/ red P α-halogenated
Zelinsky reaction hydrogen atom carboxylic acid

Hoffmann Primary aliphatic amine + HgCl2/ CH3CH2-N=C=S +

mustard oil CS2 HgS(black)
reaction
Hunsdiecker Ag salt of carboxylic acid Br2/CCl4, 800C Alkyl or aryl bromide
reaction
Kolbe electrolytic Alkali metal salt of Electrolysis Alkane, alkene, alkyne
reaction carboxylic acid

Mendius reaction Alkyl or aryl cyanide Na/C2H5OH Primary amine

Rosenmund Acid chloride H2, Pd/BaSO4 aldehyde

reduction boiling xylene

Sabatier- Unsaturated hydrocarbon Raney Ni/H2, Alkane

Senderens 200-3000C
Reaction

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Sandmeyer CuCl/HCl or Halo or cyanobenzene

reaction CuBr/HBr or
CuCN/KCN, heat

Gattermann Cu/HX(HBr/HCl) Halobenzene

Reaction

Schotten- (phenol or aniline or alcohol) NaOH + C6H5COCl

Baumann
reaction

Stephen reaction Alkyl cyanide (i)SnCl2/HCl (ii) H2O Aldehyde

Williamson Alkyl halide Sodium alkoxide or Ether

synthesis sodium phenoxide

Wurtz-Fitting Alkyl halide + aryl halid Na/dry ether Alkyl benzene

reaction

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CHAPTER – 13

POLYMERS
ADDITION POLYMERS
S.No Name of Polymer Starting Materials Nature of
Polymer
I. Polyolefins
1. Polyethylene or Polyethene CH2=CH2 Low density
homopolymer
(branched
chain growth)
2. Polypropylene or Polypropene CH3CH=CH2 Homopolymer,
linear, chain
growth
3. Polystyrene C6H5CH=CH2 Homopolymer,
linear, chain
growth
II. Polydiences
1. Neoprene Homopolymer,
chain growth

2. Buna S(Styrene-Butadiene, Copolymer,

Rubber) SBR or GRS chain growth
III. Polyacrylates
1. Polymethylmethacrylate(Flexiglass Homopolymer
Lucite, Acrylite or Perspex PMMA
2. Polyethylacrylate Homopolymer
3. Polyacrylonitrile or Orlon PAN Homopolymer
IV. Polyhalofins
1. Polyvinyl chloride PVC Homopolymer,
chain growth
2. Polytetrafluoroethylene or Teflon F2C=CF2 Homopolymer
PTFE
3. Polymonochlorotrifluoro-ethlene CICF=CF2 Homopolymer
PCTFE

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CONDENSATION POLYMERS
S.N Name of Polymer Starting Materials Nature
o of
Polymer
I. Polyesters
1. Terylene or Dacron Copolymer,
step growth,
linear

2. Glyptal or Alkyl resin Copolymer,

linear step
growth,

II. Polyamides
1. Nylon-6,6 Copolymer,
linear step
growth,

2. Nylon-6,10 Copolymer,
Linear
chain
growth
3. Nylon-6 Homopoly
mer, linear

Formaldehyde resins
1. Phenolformaldehyde resin or Phenol and formaldehyde Copolymer,
Bakelite step growth
2. Melamine formaldehyde Melamine and formaldehyde Copolymer,
step growth

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CHAPTER – 14

CARBOHYDRATES
 Carbohydrates and defined as optically active Mutarotation : When either form of D-
polyhydroxy aldehydes or ketones or the compound Glucose is placed in aq. Solution it slowly
which produce such units on hydrolysis. form the other via open chain aldehyde and
 Monosaccharide(CnH2nOn) : single unit, can’t be gradual change in specific rotation until
hydrolysed : Glucose and Fructose.
specific rotation ( 52.50) is reached.
 Oligosaccharides gives two to ten monosaccharides on
hydrolysis.
 Disaccharides (by glycosydic linkage)

Anomer’s : Differ in configuration at 1st

carbon due to hemi(acetal or ketal) ring
formation. The new-asymmetric carbon is
referred to as Anomeric carbon.
 Polysaccharide : contain more than ten monosaccharide Epimer’s : Diastereomers which differ in
units conformation at any one chiral carbon
(C6H10O5)n : Starch & Cellulose Eg. D-Glucose & D-mannose
TYPE OF SUGAR D- Glucose & D-Galactose
Give test Reducing Non reducing Sucrose:
Tollen’s reagent +ve test -ve test
Fehling reagent +ve test -ve test
Benedict test +ve test -ve test
Mutarotation Yes No
Functional unit

Maltose:

Example All Disaccharide

monosaccharides Sucrose
Glucose Polysaccharide
Fructose Starch
Mannose cellulose
Galactose
Disaccharide
Maltose
Lactose Lactose:

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CHAPTER – 14
 Starch: (Amylose & Amylopectin)
 Amylose: (Straight chain):

(i) Soluble in H2O & gives blue colour with I2

 Amylopectin(Branch chain): (C6H12O5)n

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