Name reactions for mains.pdf

DISTINCTION BETWEEN PAIRS OF COMPOUNDS
UNSATURATION TEST

TEST FOR TERMINAL ALKYNE
NATURE OF X-GROUP IN C–X BOND

DISTINCTION BETWEEN 1°,2° AND 3° ALCOHOLS

DISTINCTION BETWEEN 1°,2° AND 3° ALCOHOLS
PHENOL

CARBONYL GROUP

ALDEHYDE GROUP

AROMATIC ALDEHYDE GROUP
CARBOXYLIC GROUP

FORMIC ACID
AMINES
AMINES (1°, 2° & 3°) (Hinsberg's test)

1. Chloroethane and Chlorobenzene
2. Chlorocyclohexane and chlorobenzene

3. Chloroethane and Bromoethane
4. Benzyl chloride and chlorobenzene

5. Ethyl Chloride and Vinyl Chloride
6. n-Propyl Alcohol and iso-propyl Alcohol

7. Ethyl alcohol and methyl alcohol (Iodoform test)
8. Ethyl alcohol and acetone (2, 4 – DNP)

9. Phenol and ethyl alcohol (Neutral FeCl3
)
10. Benzoic acid and phenol (NaHCO3
)

11. Propanone and propanol (2, 4 - DNP)

12. Propanal and propanone (Tollen’s and Fehling reagent)

13. Ethanal and Propanal (Iodoform Test)
14. Pentan-2-one and pentan-3-one (Iodoform Test)

14. Pentan-2-one and pentan-3-one (Iodoform Test)
15. Propanal and benzaldehyde (Fehling solution)

16. Methanoic acid and ethanoic acid (Tollen's & Fehling solution)
17. Ethanal and Methanal (Iodoform Test)

18. Acetophenone and Benzophenone (Iodoform test)
19. Benzoic acid and ethylbenzoate

20. Benzaldehyde and acetophenone (Tollen's test)
21. Methyl amine and dimethyl amine (Isocyanide test)

22. Aniline and Ethyl Amine (Diazotisation)

23. Aniline and N-methylaniline (Isocyanide test)
24. Aniline and Benzylamine (Diazotisation + phenol)

24. Aniline and Benzylamine (Diazotisation + phenol)
25. Glucose and fructose
26. Glucose and sucrose

27. Glucose and starch

Alcoholic KOH R–X ⟶ Alkene; Elimination
Aluminium Ethoxide
Aldehyde ⟶ Ester
(Tishchenko Reaction)
Aqueous KOH/NaOH R–X ⟶ ROH
Nucleophilic substitution reaction also
used for Cannizzaro reaction
Baeyer’s Reagent
(Alkaline cold dilute KMnO4)
Alkene ⟶ 1.2 diol
(used to detect unsaturation)
RCH=O R−C−O−CH2
R
||
O
RCH=CHR’ R−CH−CHR’
|
OH
|
OH
(Syn)
Organic reagents and its uses

Bromine water (i) used to detect unsaturation.
(ii)
(iii)
2,4,6-tribromophenol
Benedict’s solution Used to detect aldehyde group
RCHO ⟶ RCO3
–
[ketone gives –ve test]
Cu2
Cl2
+ NH4
OH
(Fehling solution)
Used to Detect Terminal Alkyne
Red Precipitate observed.
NH2
Br
Br
Br
NH2
OH
Br
Br
Br
OH

CrO2
Cl2
Etard reaction
CrO3
(i) RCH2
OH ⟶ RCHO.
(ii) R2
CHOH ⟶ R2
C=O
(iii) R3
COH ⟶ no reaction
CCl4
+ OH
(Reimer Tiemann) + p-product
CO + HCl + AlCl3
+ p-product
Gattermann koch reaction
CH2
CH=O
CO2
−
OH OH
CH=O
OH OH
–

HCN + HCl + AlCl3
Gattermann Aldehyde Synthesis
CHCl3
+ KOH (i)
(Reimer Tiemann)
(ii) RNH2
⟶ RNC (Carbylamine reaction)
(used to detect 1st Amine)
(Isocyanide test)
CO2
+ OH–
(high temp + pressure)
Cu/Δ (i) RCH2
OH ⟶ RCHO.
(ii) R2
CHOH ⟶ R2
C=O
(iii)
CH=O
OH OH
CH=O
OH OH
CO2
−
OH OH
H3
C−C−OH
|
CH3
CH3
CH3
CH3
|
H2
C=C

2,4 – D.N.P. Used to detect carbonyl group
(orange ppt observed)
DMSO Polar aprotic solvent: favour SN
2 mechanism
Fe + Br2
/FeBr3
Fehling solution Used to identify – CH=O group.
PhCHO gives –ve test
Observation red ppt of Cu2
O formed
Grignard Reagent Follows (i) Acid base reaction
(ii) NAR
(iii) NSR
H2
(Pd/CaCO3
)
Quinoline
Lindlar catalyst:
R–C≡C–R R–CH=CH–R(cis)
Br

H3
PO2
(Sodium stannite also can be used for this purpose)
HN3
+ H2
SO4
(Schmidt Reaction)
H3
PO4
/Δ
or
H2
SO4
/Δ
Saytzeﬀ product: C+
mechanism;
Rearranged alkene can be formed
HNO2
(NaNO2
+ HCl) (i) RNH2
⟶ R–OH;
(ii) PhNH2
⟶ PhN2
+
(0 – 5o
C)
(iii) PhNH2
⟶ PhOH (High temperature)
(iv)
N2
+
RNH2
R−C−OH
||
O
N=O
OH OH OH
NO
+
RCH=CH2
RCH−CH3
|
OH

HlO4
(Periodic acid)
Oxidative cleavage of diol
H2
(Ni) H2
(Ni) can reduce)
(i)
(ii)
(iii) RCN ⟶ RCH2
NH2
;
–C=C– ⟶ –CH2
–CH2
–,
–HC≡CH– ⟶ –CH2
–CH2
–
H2
(Pd/BaSO4
)
Quinoline
(Rosenmund reduction)
Jones Reagent
(CrO3
+ dil. H2
SO4
+ acetone)
(i) RCH2
OH ⟶ RCOOH;
(ii) R2
CHOH ⟶ R2
C=O
RCH=O + R’CH=O
RCH−CH−R’
|
OH
|
OH
R2
CHOH
R−C−R
||
O
RCH2
OH
R−C−H
||
O
RCH=O
R−C−Cl
||
O

KHSO4
Dehydrating Reagent
K2
Cr2
O7
/H+
(i) RCH2
OH ⟶ RCO2
H;
(ii) R2
CHOH ⟶ R2
C = O
MnO2
(i) CH3
–CH=CH–CH2
–OH ⟶ CH3
–CH=CH–CH=O
(ii)PhCH2
OH ⟶ PhCH=O
To oxidise allylic/benzylic hydroxyl group into
corresponding carbonyl.
NaHCO3
NaHSO3
[White crystals, soluble in water used to separate
carbonyl from non-carbonyl compound]
CH2
=CH−CH=O
CH2
−CH−CH2
−OH
|
OH
|
OH
14
RCO2
−Na+
+
CO2
↑
RCO2
H
14
NaHCO3
RC
R−C−R
||
O
|
R
OH
SO3
−
Na+

NaOH(aq) (i) RX ⟶ R–OH;
(ii)
Basic hydrolysis of ester
(iii) HCHO HCOO–
+ CH3
OH (cannizaro)
(iv) H3
C–CH=O H3
C–CH=CH–CH=O
(Aldol condensation)
Ninhydrin Detection of amino acid
Observation purple coloured ion
NaOR Strong base:
(i)
(Saytzeﬀ Product E2
elimination)
(ii)
(claisen condensation) (β-keto ester)
R−C−OR’
||
O
NaOH
(H2
O)
R−C−O−
||
O
+ R’OH
RCH−CH2
−R
|
X
RCH=CH−R
H3
C−C−OEt
||
O
||
O
H3
C−C−CH2
−C−OEt
||
O
OH–
OH–
heat

NaOH + X2
(i)
(Haloform reaction)
(ii)
(Hoﬀman Degradation)
NaOH + CaO RCO2
H ⟶ RH
NaOX Same as NaOH + X2
NBS
(i)
(ii) PhCH3
⟶ PhCH2
– Br
NaNO2
+ HCl RNH2
⟶ R–OH
RC−CH3
||
O
-CHI3
RCO2
−
Br
R−C−NH2
||
O
RNH2

NaNH2
in paraﬃn Non-terminal Alkyne ⟶ Terminal Alkyne
(2-Butyne ⟶ 1-butyne)
Na/EtOH reduce all except c/c double & triple bond
Zn(Hg) + HCl ⟶
Clemmensen reduction
NH2
⟶ NH2
/OH–
R–CO–R ⟶ R–CH2
–R
Wolf Kishner
Na in Liq. NH3
(Birch reduction)
(trans alkene)
R−C−R
||
O
R−CH2
−R
C=C
R−C≡CR
H
R
R
H

OsO4
+ H2
O ⟶
(syn-addition)
O3
R–CH=CH–R R⟶CHO + R–CHO
[Ozonolysis process]
Oxirane followed by H+
RMgX ⟶ RCH2
–CH2
–OH
PCC (i) RCH2
OH ⟶ RCHO,
(ii) R2
CHOH ⟶ R2
C=O
(iii) R3
COH ⟶ no reaction
[Mild oxidizing reagent]
P(red) + Br2
(i)
(HVZ reaction)
(ii) ROH ⟶ R-Br
RCH=CHR RCH−CH−R
|
OH
|
OH
CH3
CO2
H H2
C−CO2
H
|
Br
O3
H2
OZn

P(red) + HI
(Strong reducing agent can
reduce any oxygen or
halogen containing
compound to alkane)
CH3
CO2
H ⟶ CH3
–CH3
CH3
CH=O ⟶ CH3
–CH3
CH3
CH3
OH ⟶ CH3
–CH3
Perbenzoic acid
R’ having more migrating tendency than R
(Baeyer Villiger Oxidation)
RCl + AlCl3
Friedel craft alkylation
RCOCl + AlCl3
Friedel craft acylation
R−C−R’
||
O
R−C−OR’
||
O
R
C−R
||
O

Ester formed (Esteriﬁcation reaction)
SnCl2
+ HCl (i) R–N=N–R’ ⟶ RNH2
+ R’NH2
(ii)
(iii) RCN ⟶ RCH = O Stephen reduction
Sn + HCl (i)
(ii) RCN ⟶ R–CH2
NH2
Silver salt RCOOAg Br2
/CCl4
/Δ⟶RBr + CO2
+ AgBr
Hunsdiecker reaction
ROH + R−C−OH
||
O
NO2
NH2
NO2
NH2

(i) AgOH/moist Ag2
O R4
NX ⟶ R4
NOH;
SOCl2
Tollens Reagent –CH=O ⟶ –CO2
–
+ Ag
(Shining silver mirror)
(I) 𝝰-hydroxy ketone,
Ph–NH–OH, HCO2
H gives positive test
(II) Reagent also used to distinguish
(i)
(ii) HCOOH Vs other acid
(III) ketone gives –ve test;
R−C−OH/R−OH
||
O
R−C−Cl/R−Cl
||
O
−C=O
H
|
−C−R
||
O
vs
–
+
+ –

Benzene sulphonyl chloride
(Hinsberg reagent)
It is used to distinguish and separate 1o
, 2o
and 3o
amines.
Tetraethyl lead Used as antiknock compound
V2
O5
(I)
(II)
V2
O5
/O2
500°
V2
O5
/O2
300°
O
O
O
HC
||
HC
OH

ORGANIC NAME REACTIONS
● Aldol Condensation
● Claisen Condensation
● Perkin Condensation
● Benzoin Condensation
– –

● Haloform Reaction
● Carbylamine Test
● Reimer Tiemann Reaction
Nutshell Review and Preview of ORGANIC NAME REACTIONS

● Kolbe's Schmidt Reaction
● Hoﬀmann Bromamide Degradation
● Curtius Reaction
● Schmidt Reaction

● Cannizzaro reaction
● Baeyer villiger
oxidation

● Cumene
● Pinacol Pinacolone rearrangement

● Birch Reduction
● Gabriel Synthesis

ORGANIC NAME REACTIONS
Name Reactant Reagent Product
Clemmensen
Reduction
Aldehyde & Ketone Zn-Hg/conc. HCl Alkane
Coupling
Reaction
NaOH (phenol)
HCl (Aniline)
Azo Dye
(Detection of OH or
NH2
gr)
Diazotization NaNO2
+ HCl
0o
– 5o
C
Etard reaction CrO2
Cl2
/CS2
Fittig Reaction Halo benzene Na/Dry ether Diphenyl
+ OR
N2
+
Cl–
OH NH2
NH2
:
CH3
N+
≡NCl−
O
H

Friedel Craft
alkylation
Anhydrous AlCl3
Alkyl Benzene
Friedel Craft
acylation
Anhydrous AlCl3
Acyl Benzene
Gattermann
aldehyde
synthesis
C6
H6
HCN +
HCl/ZnCl2
/H3
O+ Benzaldehyde
Gattermann-Koc
h reaction
C6
H6
(CO + HCl) anhy AlCl3
Benzaldehyde
Hell-Volhard
-Zelinsky
reaction
Carboxylic acid having
𝝰-hydrogen atom
Br2
/red P
𝝰-halogenated
carboxylic acid
+ R — X
+ R—C—Cl or (RCO)2
O
O

Hoﬀmann
mustard oil
reaction
primary aliphatic
amine + CS2
HgCl2
/∆
CH3
CH2
–N=C=S + HgS
(black)
Hunsdiecker
reaction
Ag salt of
carboxylic acid
Br2
/CCl4
, 80o
C Alkyl or aryl bromide
Kolbe electrolytic
reaction
Alkali metal salt of
carboxylic acid
electrolysis
Alkane, alkene and
alkyne
Mendius reaction
alkyl or aryl
cyanide
Na/C2
H5
OH Primary amine
Rosenmund
reduction
Acid chloride
H2
, Pd/BaSO4
boiling xylene
aldehyde
Sabatier-Sendere
ns reaction
Unsaturated
hydrocarbon
Raney Ni/H2
,
200–300o
C
Alkane
+

Sandmeyer reaction C6
H5
N2
+
Cl– CuCl/HCl or CuBr/HBr
or CuCN/KCN, heat
Halo or cyanobenzene
Gattermann reaction C6
H5
N2
+
Cl–
Cu/HX(HBr/HCl) Halobenzene
Schotten-Baumann
reaction
(phenol or aniline or
alcohol)
NaOH + C6
H5
COCl
Benzolytated product
Stephen reaction alkyl cyanide (i) SnCl2
/HCl (ii) H2
O Aldehyde
Williamson synthesis alkyl halide
sodium alkoxide or
sodium phenoxide
Ether
Wurtz-Fittig reaction alkyl halide + aryl halide Na/dry ether alkyl benzene
O−C−CH3
||
O
NH−C−CH3
||
O

Alkanes
R—H
ALKANES
Methods of preparation Chemical properties
R–CH=CH2
R–C≡C–H
H2
Pt
Reducing agent
Na-dry ether
Wurtz reaction
Zn,R’-X/
R2
Zn-Frankland reagent
R–X
Li.Cul,R’-X/Corey house
R2
CuLi-Gillmann’s reagent
HNO2
(vapours)
450o
C
X2
/hv (F2
> Cl2
> Br2
> I2
)
Catalytic oxidation
KMnO4
Complete oxidation
R–NO2
R–X
R3
C–OH
nCO2
+ (n + 1)H2
O
(3n + 1)
2 O2

Alkanes
R—H
R—C—R
||
O
R–CH2
–I
conc. H2
SO4
+ SO3
R–CH2
–OH
R–CHO
R–COOH
Red P + Hl
R–CHO
or
Zn+Hg/HCl-Clemmensen
NH2
–NH3
/OH
Wolf Kishner
⊝
NaOH + CaO
Sodalime/Δ
(Decarboxylation)
Kolbe’s
electrolysis
H—2
(Active—H)
RCOOH
RCOOH
R–MgX
CH2
N2
/Δ
Insertion of carbene
Pyrolysis
Higher alkanes
Alkenes + alkanes
Cr2
O3
+ Al2
O3
+ 600o
C
aromatization
Aromatic
hydrocarbon
AlCl3
/HCl, Δ
isomerisation Isomeric alkanes
R–SO3
H

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