ALDEHYDE AND KETONE

Crux – Aldehyde & Ketones give nucleophilic addition reactions and 4 named reactions viz.
ACPH

Reagents Uses
Tollens reagent, Ag(NH3)2]+ Oxidizes aldehydes and  - hydroxy ketones (check it)
Fehlings solution Oxidises aldehydes to carboxylic acids but does not oxidizes
benzaldehyde
OH-/ X2 Haloform reaction
LiAlH4 Reduces Aldehyde, ketones,ester and acid chloride to
corresponding alcohol
NaBH4 Reduces A & K to corresponding alcohol but does not affects
ester and acid chloride
Zn / Hg – conc. HCl Reduces A & K to corresponding alkane
(Clemmenson reduction)
N2H4, glycol,KOH (Wolf Reduces A & K to corresponding alkane
Kishner reduction)
Mg – Hg in benzene (H2O) Reduces ketones to pinacole
SeO2 Oxidizes CH3,CH2- group adjacent to carbonyl group of A &
K to C=O group
Peracids Oxidizes ketones to esters by inserting O atom
(PFA,PBA,MCPBA)
Dil. OH- Aldehydes and ketones having  atom give aldol
condensation
50% aq OH- or ethanolic Aldehydes lacking  H – atom gives cannizaro reaction in
OH- which alcohol and carboxylic acid is produced (disproporotion
reaction)
H2 – Pd, BaSO4, boiling Converts acid chloride to aldehyde (Rosenmund reaction)
Xylene
NH3 or NH2-Z Aldehyde and ketones react with ammonia and its derivative
under acidic condition, followed by loss of water molecule to
give condensation product
NaNO2 – HCl (HNO2) Converts aniline to diazonium salt
Aldehyde and ketone react with alcohols under acidic condition to give hemiacetal and acetal

HYDROCARBON
Crux – Alkene & alkyne give electrophilic addition reactions whereas alkane give free radical
reactions.

Reagents
H2, Ni/Pt/Pd
Pd/CaCO3+Quinoline &
Lead acetate (Poison)
[lindlar's catalyst]
Na/Liq. NH3
Uses
Syn addition of hydrogen across C=C and C  C
Adds one equivalent of H2 across C  C (converts alkyne to
alkene)
Trans addition of H2 to Non-Terminal alkynes

Dilute H+ Markownikoffs addition of water across C=C

BH3; H2O2; OH–, HBO Anti Mark. addition of water across C=C.
H2O;Hg(OAC)2/NaBH4,OH– Markownkoff's addition of H2O across C=C.

HX (HCl,HBr,HI) Markownikoffs addition of HX across C=C

HBr in peroxide
X2 (Cl2,Br2,I2)
Cold alk. KMnO4
Hot conc. alk. KMnO4
Peracids
(PFA,PBA,MCPBA)
OsO4 in ether,H2O,Na2SO3
Heated Fe,Ni or Cu tube
O3, / Zn dust - AcOH
O3, / H2O2
NBS,NClS or SO2Cl2 in
peroxide
X2 in sunlight or peroxide
Anti Markownikoffs addition of HBr across C=C
Anti addition of X2 across C=C
Syn addition 2 OH groups across C=C
C=C rupture takes place and various oxidized products are
formed.
Anti addition of 2 OH groups across C=C
Syn addition of 2 OH groups across C=C
Polymerization of alkyne takes place
Reductive ozonolysis of alkene, aldehyde and or ketones are
produced
Oxidative ozonolysis of alkene, acid and or ketones are
produced
Alkynes on ozonolysis first give diketones and finally give
carboxylic acids.
 halogenation to C=C takes place
Halogenation of alkane takes place

ETHER
Aliphatic ether – protonated ether – SN1, SN2
Cyclic ether – acidic condition – SN1 and basic condition - SN2
For ether preparation better SN2 – better is the yield

ALCOHOL

CRUX - Alcohol – protonated alcohol - SN1,E1 (2o,3o, allylic, benzylic etc) or

rearrangement reaction
- SN2 (1o, methyl)
Reagents Uses
Conc. HCl,anhyd ZnCl2 Converts R-OH to R-Cl (used as a test to distinguish between
(Lucas reagent) 1o,2o,3o alcohol)
HX (HCl,HBr,HI) Converts R-OH to R-X
NaX,H2SO4 Converts R-OH to R-X
KI-H3PO4 or HI Changes R-OH to R-I
PCl5,PCl3,P + Converts alcohol to corresponding alkyl haide
X2,SOCl2,PBr3,TsCl + NaCl
PCC (Pyridinium chloro Selective reagent for converting 1o alcohol to aldehyde
chromate)
Heated Cu or Ag Converts 1o and 2o alcohol to aldehyde and ketone
respectively and 3o alcohol to alkene
 ,KMnO4 / H+ or OH / -
All Strong O.A, converts alcohol to carboxylic acids
 K2Cr2O7 / H / 
+

 Conc. HNO3
HIO4 1, 2 – dicarbonyl or 1, 2 – hydroxyl or combination of these
two on oxidation with periodic acid produces carbonyl
 compounds – aldehydes, ketones or acids

- Alcohols react with carboxylic acids under acidic condition to give estes
- 1,2 – diol or pinacol rearrange under acidic condition to give ketones or pinacolone

ALKYL HALIDE
CRUX – Alkyl halide –

Reagents Uses
Alc. KOH Converts alkyl halide to alkene
NaI-acetone,  (Finkelstien For preparing RI from R-Cl or R-Br
reaction)
Hg2F2 ,  Converts R-Cl to R-F
Br2 ,CCl4 ,  (Hunsdiecker Silver salts of carboxylic acid are converted to alkyl bromide
reaction) (RCOO-Ag+   R-Br + CO2 + AgBr )

Aq.KOH or Moist Ag2O (or Converts R-X 

 R-OH
AgOH)
RO-Na+ (sod. Alkoxide) Converts R-X to R-O-R, if alkyl halide is primary.
(Williamson ether synthesis)
Dry Ag2O R-X   R-O-R
Alc. KCN R-X to R-CN
Alc. AgCN RX to RNC
Na/EtOH RCN   RCH2NH2 (mendius reaction)

Alc. NH3 R-X to R-NH2 ; R-X(xs)   then R-NH2/R2NH/R3N and

R4N+X- (Hoffman ammonolysis)
KNO2 R-X   R-O-NO (alkyl nitrite)
AgNO2 R-X   R-NO2 (nitro alkane)
Alc. R’COOAg R-X   R-COOR’ (ester)
Zn-EtOH Reduces R-X to R-H
Zn-HCl/Sn-HCl/LiAlH4 Reduces R-X to R-H
Mg – dry ether R-X + Mg dry ether

 R-MgX (Grignard reagent)
AlCl3 – 573K Isomerisation of haloalkanes takes place

PHENOL

CRUX – Phenol gives acid – base reaction or Named reactions (EAS). Industrially phenol is
prepared from cumene process

Reagents Uses
NaOH,CO2,125oC,Press,followed Introduces COOH group in phenol (Kolbe’s reaction)
by hydrolysis
NaOH,CHCl3,followed by Introduces CHO group in phenol (Reimer Tiemann
hydrolysis reaction)
HCN,HCl,ZnCl2, followed by Introduces CHO group in phenol (Gattermann reaction)
hydrolysis
Zn dust Converts phenol to benzene
Pthaleic anhydride Phenol condenses with pthaleic anhydride to give acid
base indicator Phenolpthalein
Neutral FeCl3 Gives blue or violet colour with phenol, used as a test
Aniline + HNO2 (NaNO2 + HCl) Coupling of diazonium cation with phenol at ortho and
para position takes place
NaOH, KOH (or any strong base) Acid base reaction of phenol (salt + H2O
NaH (or any metal hydride) Acid base reaction of phenol (salt + H2)

CAD
CRUX – Carboxylic acids and their derivatives give nucleophilic substitution reaction or 2
named reactions viz. Beckmann or Hoffman reaction.

Reagents Uses
Br2 + KOH Converts amides to primary amines (RCONH2 to RNH2)
H+ Oximes convert into substituted amides under acidic condition

EAS
Reagents Source of E+
NaNO2 + HCl (or HNO2) NO2+
Conc. H2SO4,oleum,liquid SO2
SO2
X2 + Lewis Acid X+
(X2 = Cl2,Br2,I2)
R-Cl + Lewis acid R+
RCOCl + Lewis acid RCO+
RCOOCOR + Lewis acid RCO+
RCOOH + Strong mineral RCO+
acid
RC=C + dilH+ Stable alkyl carbocation
R-OH + H+ (R-OH = 2o,3o) R+
NO2BF4,DMSO (solvent), NO2+
heat
Aniline + HNO2 Diazonium cation