Chemistry HandBook C HAP TE R

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ORGANIC REAGENTS
1. Alcoholic KOH 10. CCl4 + OH— (Reimer Tiemann)
R—X Alkene ; Elimination OH OH
CO2
2. Aluminium Ethoxide + p-Product
RCH=O R C O CH2R (Tischenko Reaction)
O 11. CO + HCl + AlCl3
(Aldehyde) (Ester)
OH OH
CH O
3. Aqueous KOH/NaOH + p-Product
R—X ROH
Nucleophilic substitution reaction also used for Gatterman koch reaction
Cannizzaro reaction with aldehyde.
OH OH
CH O
4. Baeyer's Reagent (Alkaline cold dilute KMnO4) 12. HCN + HCl + AlCl3
RCH=CHR' RCH—CHR'
OH OH Gatterman Aldehyde Synthesis
(Syn)
alkene 1, 2 diol 13. CHCl3 + KOH
(used to detect unsaturation) OH OH
CH O
5. Bromine water (i)
(i) used to detect unsaturation;
Reimer Tiemann reaction
NH 2 NH 2 OH
OH
(ii) Br Br (iii) Br Br (ii) RNH2 RNC (Carbyl amine reaction)
(used to detect 1° Amine) (Isocyanide test)

Br Br
2,4,6-tribromoaniline 2,4,6-tribromophenol
14. CO2 + OH– (high temp. + Pressure)
6. Benedict's solution OH OH
Used to detect aldehyde group RCHO RCO2– CO2 + p–Product
[ketone gives -ve test]
Kolbe's reaction
7. Cu2Cl2 + NH4OH
Used to Detect Terminal Alkyne 15. Cu/
Red Precipitate observed (i) RCH2OH RCHO,
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(ii) R2CHOH R2C=O

8. CrO2Cl2
CH3 CH3
CH3 CH O
(iii) H3C–C–OH H2C=C
CH3 CH3
Etard reaction
16. 2,4 – D.N.P.
9. CrO3
(i) RCH2OH RCHO, used to detect carbonyl group (orange ppt observed)
(ii) R2CHOH R2C=O
(iii) R3COH no reaction 17. DMSO
Polar aprotic solvent: favour SN2 mechanism

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

Br (i) R C R R2CHOH
O
(ii) R–C–H RCH2OH
19. Fehling solution O
used to identify – CH=O group. (iii) RCN RCH2NH2; –C C– –CH2–CH2–,
PhCHO gives –ve test –HC=CH– –CH2—CH2–
Observation: red ppt of Cu2O formed
29. H 2(Pd/BaSO 4)
Quinoline
20. Grignard Reagent
Follows (i) Acid base reaction (ii) NAR (iii) NSR R C Cl RCH= O
O (Rosenmund reduction)
21. H2(Pd/CaCO3) Quinoline (Lindlar catalyst)
R—C C—R R—CH=CH—R (cis) 30. Jones Reagent (CrO3 + dil. H2SO4+ acetone)
(i) RCH2OH RCH=O; (ii) R2CHOH R2C=O
22. H 3PO 2
31. KHSO4 Dehydrating Reagent
+
N2 CH2 CH CH2 OH CH2 CH CH O

OH OH
32. K2Cr 2O7/H +
23. HN3 + H 2SO4
(i) RCH2OH RCO2H; (ii) R2CHOH R2C = O
R C OH RNH2
O 33. MnO2
(Schmidt Reaction) (i) CH3—CH=CH—CH2—OH CH3—CH=CH—CH=O
(ii) PhCH2OH PhCH=O
24. H3PO4/
To oxidise allylic / benzylic hydroxyl group into
H3PO4 Same as H2SO4/
corresponding carbonyl.

25. H2SO4/ 34. NaHCO3

RCH CH 3 RCH CH 2 14
14
NaH C O3
OH RCO2H RCO2 Na CO2
Saytzeff product; C+ mechanism;
Rearranged alkene can be formed 35. NaHSO3
OH
26. HNO2 (NaNO2 + HCl) R C R RC
+
(i) RNH2 R—OH; SO3Na
O
(ii) PhNH2 PhN2+ (0 – 5°C)
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[White crystals, soluble in water used to separate

(iii) PhNH2 PhOH (high temperature) carbonyl from noncarbonyl compound]
OH OH OH
N O 36. NaOH(aq)
(iv) + (i) R—X R—OH
NaOH
NO
(ii) R C OR' (H2O) R C O + R'OH
O O
27. HIO4 (Periodic acid)
Basic hydrolysis of ester
RCH CH R' RCH=O + R'CH=O
(iii) HCHO OH —
HCO2 CH3 OH (cannizaro)
OH OH
Oxidative cleavage of diol OH —
(iv) H3 C CH O H3 C CH CH CH O
(Aldol condensation)

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

Detection of amino acid
R H
Observation : Purple coloured ion R C CR C C
H R
38. NaOR
(trans alkene)
Strong base :
49. OsO4 + H2O
(i) RCH CH2 R RCH CH R
RCH CHR RCH CH R
X
(Saytzeff Product : E2 elimination)
(syn addition) OH OH

(ii) H3C C OEt H3C C CH2 C OEt O3

50. O3 : R–CH CH–R R–CHO+R–CHO
O O O H2O\Zn (Ozonolysis process)
(claisen condensation) ( keto ester)
51. Oxirane followed by H +

RMgX RCH2—CH2—OH
39. NaOH + X2 or NaOX
(i) RC CH3 RCO2 (Haloform reaction) 52. PCC
CHI3
O (i) RCH2OH RCHO,
(ii) R2CHOH R2C=O
(ii) R C NH2 RNH2 (Hoffman Degradation) (iii) R3COH no reaction
O (Mild oxidizing reagent)

53. P(red) + Br 2
40. NaOH + CaO
RCO2H RH (i) CH3CO2H H2 C CO2H (HVZ reaction)
Br
41. MnO / 300°C (ii) ROH R —Br
used for –CO2 & –H2O in carboxylic acid.
54. P (red) + HI
42. NBS CH3CO2H CH3—CH3
Br
CH3CH=O CH3—CH3
CH3CH2OH CH3—CH3
(i) ; (ii) PhCH3 PhCH2—Br (strong reducing agent can reduce any oxygen
or halogen containing compound to alkane)

43. NaNO2 + HCl 55. Perbenzoic acid [Baeyer Villiger Oxidation]

RNH2 R—OH
R C R' R C OR'
44. NaNH2 in paraffin O O
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Non-terminal Alkyne Terminal Alkyne R' having more migrating tendency than R
(2–Butyne 1–butyne)
56. RCl+AlCl3 [Friedel craft alkylation]
45. Na/EtOH
Reduce all except c/c double & triple bond R

46. Zn(Hg) + HCl Clemmensen's reduction

R C R R CH2 R 57. RCOCl + AlCl3 [Friedel craft acylation]
O C R
47. NH2 –NH 2/OH [Wolf Kishner reduction]
– O
R–CO–R R–CH2–R

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conc. 64. Tollens Reagent Test

58. ROH +R C OH H2 SO4 R C OR
(i) Terminal alkyne gives
O O (ii) Aldehyde Group gives
Ester formed (Esterification reaction) (iii) Ketone gives –ve test
(iv) -hydroxy ketone gives
59. SnCl2 + HCl (v) HCOOH gives
(i) R—N=N—R' RNH2 + R'NH2 (vi) Hemi acetal gives
NO2 NH2 (vii) PhNH–OH gives
(ii)
65. Benzene sulphonyl chloride
It is used to distinguish and separate (Hinsberg reagent)
(iii) RCN RCH=O [Stephen reduction]
1°, 2° and 3° amines.
60. Sn + HCl
66. Tetra ethyl lead (TEL)
NO2 NH2 Used as antiknock compound
(i)
67. V2O5
(ii) RCN R–CH2 NH2
O
61. Silver salt RCOOAg (Hunsdiecker reaction) V2O5 /O 2 HC
Br2/CCl4/ RBr +CO2+AgBr (I) 500°C
O
HC
62. AgOH/moist Ag2O; R 4 N X R 4 N OH (Maleic anhydride) O

OH
63. SOCl2
V2O5 /O 2
R C OH/R
(II)
OH R C Cl/R Cl 300°C
O O

IMPORTANT NOTES
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Nutshell review & preview of

ORGANIC NAME REACTIONS
O O O O OH O
+
OH H OH
• Aldol Condensation 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

O O O O O O O
+
EtO H
H3 C C OEt EtO C CH2 C CH3 CH3 C C C OC2H5
• Claisen Condensation EtO C CH2 C CH3
H2
OC2 H5 OEt

H H O H
O O
H 3C C ONa
• Perkin Condensation C + HC C C CH 3 C C C OH
O H O O H
Cinnamic acid

O O OH
KCN
• Benzoin Condensation 2 C H EtOH C CH Benzoin

OH O O
NaOI
• Haloform Reaction H3C CH R 1 H3C C R 1
NaOH
CHI3 +R
1
C ONa
I2

H Cl CHCl H Cl OH
3
• Carbylamine Test R N C R N C R N C Isocyanide
KOH
H Cl Cl
H

H
O OH H
OH O CCl4 C O
CHCl3
C OK
• Reimer Tiemman Reaction KOH KOH
(Salicylaldehyde)
(Salicylic acid)

O H OH O
C
• Kolbe's Schimdt Reaction NaOH 125°C OH (Salicylic acid)
CO 2/H + major
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O B r2
• Hoffmann Bromamide R C N H 2 KO H R N H 2+ K 2C O 3
Degradation
O
NaN 3
• Curtius Reaction R C Cl + R NH 2
,H3O

O HN3 H3O
• Schimdt Reaction R C OH R N C O R NH2
H2SO4

O O O O O O
50% +
• Cannizzaro reaction H C H NaOH H3C C H C H
slow
RDS H C OH+H C H H C ONa +CH3 OH
H O H H

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O (i) F3C C OO H O
(peracid)
• Bayer villiger oxidation C H3C C O
(ii) H +
H3C

O–O–H
CH3–CH–CH3 CH3–C–CH 3 OH
• Cumene O
O2 HCl
+ CH3–C–CH3
130°C
Cumene
hydroperoxide

Cl

+
H +
• Pinacol-Pincolone C C Cl C C
-H 2O
rearrangement OH OH OH

Ph
C C Ph —H
+
Cl
O Ph

O
O R(+M) O R C OH COOH
Na/ Na/ Na/
• Birch Reduction liq. NH 3 ; liq. NH 3 ; liq. NH 3

R H
Na/
R C C R' liq. NH C C Na/ +
3 R C C H liq. NH R C CNa
H R ; 3 (Acid-base reaction)
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trans

O O O O
• Gabriel Synthesis C NH3 C KOH C C
N H + CH3-I
O NK N CH3
C C C C
O O O O
O
C OH
H 3O +
+ CH3NH2
C OH
O

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NAME REACTIONS
Name Reactant Reagent Product

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

N+Cl OH NH2
2
NaOH (phenol) Azo Dye
Coupling Reaction + or HCl (Aniline) (Detection of OH or NH2 gr)

.. NaNO2 + HCl +
Diazotization N H2 N NCl
0° – 5°C
O
Etard reaction H 3C CrO2Cl2/CS2 H
( Be nzalde hyde)

Fittig Reaction Halo benzene Na/Dry ether Diphenyl

Friedel Craft alkylation +R—X Anhydrous AlCl3 Alkyl Benzene

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

Gattermann aldehyde
C6H6 HCN+ HCl /ZnCl2/H 3O+ Benzaldehyde
synthesis
Gattermann-Koch
C6H6 (CO + HCl) anhy AlCl3 Benzaldehyde
reaction
Hell-Volhard-Zelinsky carboxylic acid having halogenated
Br2 / red P
reaction -hydrogen atom carboxylic acid
Hoffmann mustard oil CH3CH 2—N=C=S +HgS
primary aliphatic amine + CS2 HgCl2 /
reaction (black)
Hunsdiecker reaction Ag salt of carboxylic acid Br 2/CCl4, 80°C alkyl or aryl bromide
Kolbe electrolytic alkali metal salt of
electrolysis alkane, alkene and alkyne
reaction carboxylic acid
Mendius reaction alkyl or aryl cyanide Na/C 2H5 OH primary amine

H2, Pd/BaSO4
Rosenmund reduction acid chloride aldehyde
boiling xylene

Sabatier-Senderens Raney Ni/H2,

Unsaturated hydrocarbon Alkane
reaction 200—300°C

CuCl/HCl or CuBr/HBr or
Sandmeyer reaction C6 H 5 N 2 Cl — Halo or cyanobenzene
CuCN/KCN, heat
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Gattermann Reaction C6H5 N2 +Cl— Cu/HX(HBr/HCl) Halobenzene

benzolytated product
O
Schotten-Baumann O –C–CH3
(phenol or aniline or alcohol) NaOH + C 6H5COCl
reaction O
NH– C–CH 3

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

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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POLYMERS
ADDITION P OLYMER S

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 Cl Homopolymer, chain growth
CH2=CH-C=CH2
Chloroprene or
2-Chloro-1,3-butadiene
2 Buna S (Styrene-Butadiene, Rubber) CH2 =CH-CH=CH2 and C6 H5CH=CH2 Copolymer, chain growth
1,3-butadiene Styrene
SBR or GRS
III. Polyacrylates
1. Polymethylmethacrylate (Flexiglass CH3 Homopolymer
Lucite, Acrylite or Perspex PMMA H2C C COOCH3
2. Polyethylacrylate H2C CH COOC2H5 Homopolymer
3. Polyacrylonitrile or Orlon PAN CH2=CH—CN Homopolymer
IV. Polyhalofins
1. Polyvinyl chloride PVC CH2=CH—Cl Homopolymer, chain growth
2. Polytetrafluoroethylene or Teflon PTFE F2C=CF2 Homopolymer
3. Polymonochlorotrifluoro-ethylene PCTFE ClFC=CF2 Homopolymer
CONDENSATION POLYMERS
S.No Name of Polymer Starting Materials Nature of Polymer
I. Polyesters
O
1. Terylene or Dacron O Copolymer,
HO C C OH
HO CH2 CH2 OH
step growth, linear
Tere pht ha lic acid or
Ethylene glycol or Ethane-1,2-diol And Benzene -1,4- dicarb oxylic acid

2. Glyptal or Alkyl resin HOOC CO OH Copolymer,

HO CH2 CH2 OH and linear step growth
Ethylene glycol
Ph thalic acid or
Benzene-1,2-dicarboxylic acid

II. Polyamides
1. Nylon-6,6 O O Copolymer,
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HO C(CH2 )4 C OH and H 2 N (CH 2)6 NH2 linear, step growth

Hex amethylenediamine
Adipic acid

2 Nylon-6,10 H2 N(CH2 )6 NH2 HOOC(CH2) 8COOH Copolymer,

and
Hex amet hyle ne di ami ne Sebacic acid linear, step growth

3. Nylon-6 NH O Homopolymer,
linear

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

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CARBOHYDRATES
• Carbodydrates are defined as optically active • Mutarotation: When either form of D-glucose is
polyhydroxy aldehydes or ketones or the compound placed in aq. solution it slowly form the other via
which produce such units on hydrolysis. open chain aldehyde and gradual change in specific
rotation until specific rotation (± 52.5°) is reached.
• Monosaccharide (CnH2nOn) : single unit, can't be 6
H2C OH
H2C OH HO-CH 2 H
hydrolysed : Glucose and fructose. 5 H O H
H O OH H O H
H H H
• Oligosaccharides gives two to ten 4
OH H
1 OH H
C O OH H
monosaccharides on hydrolysis. OH 3 2
H OH OH OH
H OH H OH H OH
• Disaccharides (by glycosydic linkage) -D-Glucose [ ]0=52.5
-D-Glucose
[ ]D=+112°
[ ]D=+19°

Sucrose H3 O D. Glucose + D. Fructose; • 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
Maltose H3 O 2 D. Glucose unit carbon.
• Epimer's : Diastereomer's which differ in
Lactose H3 O D. Glucose + D. Galactose conformation at any one chiral carbon
eg. D-Glucose & D-mannose
• Polysaccharide : Contain more than ten D-Glucose & D-Galactose
monosaccharide units • Sucrose :
(C6H10O5)n : Starch & cellulose. 6
OH
5
O H O 6
CH 2 OH
H
TYPE OF SUGAR 4 H 1 O 2 5
OH H OH H
Give Test Reducing Non OH HOCH2 H
Reducing 3 2 4 3

Tollen's Reagent +ve test –ve test H OH H OH

-D-Glucose -D-Fructose (unit)
Fehling Reagent +ve test –ve test
Benedict Test +ve test –ve test (1,2 Glycosidic linkage)
Mutarotation Yes No • Maltose
O 6 6
Functional Unit C C O C C C H 2C OH H 2 C OH
OH OH
H
5
O H H 5 O H
O H O H H 4
H
4 1 1
OH H OH H
OH OR O OH
OH
: 3 2
Hemiacetal Acetal 2
(1,4 Glycosidic 3
H OH linkage) H OH
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O R O R ( -D-glucose)
Two -D-Glucose unit
OH OR
• Lactose :
Hemiketal Ketal
6
6
HO-CH2
Example All monosaccharides Disaccharide HO-CH2
H 5
Glucose Sucrose HO
5
O O OH
Fructose Polysaccharide H H
4 1 O4 1
Mannose Starch OH H OH H
Galactose cellulose H H 2 H
3 2 3
Disaccharide
H OH H OH
Maltose
lactose -D-Galactose -D-Glucose

(1,4 Glycosidic linkage)

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• Starch : (Amylose & Amylopectin)

• Amylose : (Straight Chain) :
6 6
H 2 C OH H 2 C OH CH 2–OH
5 O H H 5 O H H O H
H H H
4 1 4 1 H
OH H OH H OH
O O O O
3 2 3 2
H OH H OH H OH
( -1,4 Glycosidic linkage)
(i) Soluble in H2O & gives blue colour with I2
• Amylopectin (Branch chain) : (C6H12O5)n

6 6
H2C OH H2C OH
(C6H12 O5)n
H 5
O H H 5 O H
nH2O Diastase
H H
4 1 4 1 C 12H22O 11(maltose)
OH H OH H
HO O nH2O maltase
3 2 3 2
2C 6H12O6 -D-Glucose
H OH
6
H OH O
1,6-Glycosidic linkage
HO–CH 2 6
CH2
H O H O H Cellulose
5 H 5
H H nH2O
4
OH H 1 4
OH H 1 nC6H12O6
O O O
3 2 3 2 -D-Glucose
n
H OH H H
1,4-Glycosidic linkage

REACTION OF GLUCOSE (OPEN CHAIN STRUCTURE)

* Fructose doesn't react with Br 2/H 2O

COOH Na–Hg CH2–OH

Br2
(CH–OH)4 (CH–OH)4
H2O
CH2–OH CH2–OH
(Gluconic acid) Sorbitol
CHO
COOH (CH–OH)4 CHO
Conc. HNO3 5AcCl (CH–OAc)4
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(CH–OH)4 CH2–OH
COOH CH2–OAc
Glucose
(Saccharic acid) Glucose penta acetate

HI / Red P 3Ph–NH–NH2
CH3–(CH2)4–CH3 CH = N – NH – Ph
(n-Hexane) C = N – NH – Ph
(CHOH)3
CH2–OH
(Osazone)

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IMPORTANT NOTES

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