Reagents and Reactions

S.No Reagent /Process Function Reaction Name of the reaction ( if any) /Remarks
conditions
1 H2 /Pd or Pt Alkenes or alkynes to Room
alkanes temperature

Hydrogenation of unsaturated hydrocarbons

Aldehydes to alcohols

Reduction of aldehydes

H2 /Pd / EtOH Nitrobenzene to aniline

2 H2 / Ni Alkenes or alkynes to At 2000C

alkanes. to 3000C,
atm
pressure
Sabatier-Sanderens reaction (Hydrogenation of
unsaturated hydrocarbons) Methane can not be
prepared
H2 / Ni or Na-Hg , H2O Nitriles to amines

3 Zn/HCl or Zn/ NaOH or Alkyl halides to alkanes Nascent

Zn-Cu couple/C2H5OH or hydrogen
Zn/CH3COOH is produced Reduction of alkyl halides
4 Na/ Dry ether alkyl halides to alkanes. Heat
(Carbon -Carbon coupling)

Wurtz reaction. (Free radical mechanism)

Methane can not be prepared
Akyl halide and aryl halide
couple to give alkyl
benzenes
Wurtz- Fittig reaction
Aryl halide couple to give
Biphenyl
Fittig reaction.
5 NaOH +CaO (Soda Lime) Sodium salt of carboxylic Heating
acids to alkanes with one
carbon atom less than the Product will contain one carbon less than starting
starting carboxylic acid. material.
Decarboxylation.
6 Electrolysis Sodium or potassium salt
of carboxylic acids to
alkanes. At anode alkane,
at cathode, H2 are formed.
(Carbon -Carbon coupling Kolbe’s electrolysis
Methane can not be prepared
7a X2 Alkanes to haloalkanes Higher
temp.
(573-773
Free radical substitution. (Halogenation / nitration
K) or in the
presence of /sulphonation). Chain reaction.
diffused Rate of reaction with halogens F2 > Cl2 > Br2 > I2
Sunlight or Rate of replacement of hydrogens of alkanes is
ultraviolet 3° > 2° > 1°.
light.
During the free radical halogenation of ethane, due
Iodination
is carried to the disproportionation of ethyl free radical,
out in the ethylene and ethane are formed.
presence of During the free radical halogenation of methane, in
oxidizing the chain termination, due to the combination of
agents like methyl free radicals, ethane can be formed.
HIO3 or
HNO3 .

7b Conc.HNO3 Alkanes to nitroalkanes

7c Conc.H2SO4 Alkanes to alkane

sulphonic acid.
Lower alkanes do not
undergo nitration
/sulphonation.)
8 Cu Methane to methanol 523K/100
( O2 is one of the reactants) atm

Controlled oxidation
9 Mo2O3 Methane to methanal Heat
( O2 is one of the reactants)

Controlled oxidation
10 (CH COO)2 Mn Ethane to ethanoic acid Heat
( O2 is one of the reactants)

Controlled oxidation
11 Acidified KMnO4 Isobutane to tertiary butyl Heat
alcohol.

Controlled oxidation.

Alkenes or alkynes to
carboxylic acids or
ketones.

Acidified K2Cr2O7 or
Acidified KMnO4
And Jones reagent
(CrO3 in aq.H2SO4) 10 alcohols are oxidized to
carboxylic acids ,
20 alcohols are oxidized
to ketones

Primary and secondary

KMnO4/KOH alkyl groups on benzene are
oxidized

Na2Cr2O7 / H2SO4 Phenol to p-benzoquinone

12 Anhydrous AlCl3 /HCl n-alkanes to isoalkanes Heat

Isomerization
13 Cr2O3 or V2O5 or MoO2 n-Alkanes having six or 773K at
more carbon atoms to 10-20 atm
aromatic compounds

Aromatization (dehydrogenation) or reforming.

14 Preparation of lower Higher alkanes to lower Very high
alkanes alkanes temp

Pyrolysis or cracking
15 Partially deactivated alkynes to alkenes on
palatized charcoal treating with H2
(Lindlar’s catalyst.
(Pd/C/BaSO4 )
Controlled hydrogenation. Cis-hydrogenation

Acid chlorides to aldehydes

Rosenmund reduction.
16 Na/Liq.NH3 alkynes to alkenes on
treating with H2

Controlled hydrogenation. Trans-hydrogenation

17 Alcoholic potash 1.Alkyl halides to alkenes Heat
(potassium hydroxide
dissolved in alcohol like
C2H5OH ( forms C2H5-O-
K ,potassium ethoxide, a
base. 1. Dehydrohalogenation, β-elimination.
( Sodium ethoxide acts as Rate of reaction: Cl2 < Br2 < I2
a base when it abstracts a Rate of reaction: Tert > Sec > Pri
proton from a molecule.
Elimination reaction that
occurs in alcoholic
conditions with heat.) 2. 1,2-Dihaloalkane Heat

(Refer Aq.NaOEt)
Nucleophilic substitution)
Williamson synthesis)

18 Zn Vicinal dihalides ( if Heat

halogen atoms are present
on the adjacent carbons) to
alkenes
Dehalogenation.

1,1,2,2-tetrahaloalkanes to Heat
alkynes

Dehalogenation.

Heat
Phenol to benzene
Reduction of phenol ( ZnO is also formed )
 Alkyl halides to alkanes. Heat
(Carbon -Carbon coupling) Frankland reaction
0
19 Conc.H2SO4 Alcohols to alkenes 170 C Dehydration. β-elimination.
Ease of dehydration of alcohols: tert > sec > pri

Alcohols to ethers 1400C

Alcohols to alkyl
hydrogensulphate. 1100C

Conc.H3PO4
20 alcohols to alkenes
1670C

30 alcohols to alkenes 850C

Al2O3 (or ZnCl2) Alcohols to alkenes 3500C (or

1500C)
20. X2 / CCl4 ( X= Cl or Br) Alkenes to trans 1,2-
dihaloalkane

The reddish orange colour of bromine solution in

carbon tetrachloride is discharged when bromine
adds up to an unsaturation site. This reaction is used
as a test for unsaturation. Addition of halogens to
alkenes is an example of electrophilic addition
reaction involving cyclic halonium ion formation.
Trans -1,2-dihalo compound is the product.

Alkynes  trans 1,2-

dihaloalkenes  1,1,2,2-
tetrahaloalkane

Halogenation of alkynes. Test for unsaturation as

colour of bromine will be discharged. Electrophilic
addition reaction.
21 HX ( X= Cl or Br or I) Alkenes to alkyl halides

Single product if symmetrical alkene is used

Two products if unsymmetrical alkene is used.

Formation of major product is in accordance with
Markovnikov rule (negative part of the addendum
(adding molecule) gets attached to that carbon atom
which possesses lesser number of hydrogen atoms).
Formation of the major product is based on the stability
of intermediate carbocation.

Alkynes  vinyl halide 

geminal dihalide
Addition of HX to unsymmetrical alkynes follow
Markovnikov’s rule.

Ether to alcohol and alkyl

halide Cold & dil
When primary or
secondary alkyl groups are Order of reactivity: HI > HBr > HCl.
present, it is the lower alkyl
group that forms alkyl The
iodide (SN2 reaction). cleavage of
(Iodide attacks less ethers
substituted carbon) takes place
with If one of the alkyl groups is a tertiary group, the
concentrat halide formed is a tertiary halide.Becuase the
ed HI or reaction proceeds through SN1 mechanism.
HBr at
high temp.

Alkyl aryl ethers are cleaved at the alkyl-oxygen

bond due to the more stable aryl-oxygen bond. The
reaction yields phenol and alkyl halide.
22 HBr (not with HCl or HI) Alkenes to alkyl halides
/Peroxides

Two products if unsymmetrical alkene is used.

Formation of major product is in accordance with
Anti Markovnikov addition or peroxide effect or
Kharash effect (negative part of the addendum
(adding molecule) gets attached to that carbon atom
which possesses more number of hydrogen atoms).
Formation of the major product is based on the
stability of intermediate free radical. With HCl and
HI Anti Markovnikov addition is not followed.
(Single product if symmetrical alkene is used).
23 Cold concentrated Alkenes to alkyl hydrogen
sulphuric acid sulphate

Formation of alkyl hydrogen sulphate

24 Cold, dilute, aqueous Alkenes to glycols 273K
solution of potassium
permanganate (Baeyer’s
reagent)

Cis hydroxylation. Colour of KMnO4 is discharged.

Test for unsaturation.
26 O3 , Zn-H2O Alkenes to two carbonyl
compounds

Ozonolysis. Useful reaction to detect the position

of double bond(s).

(Cyclic alkenes and

alkynes will give product
with two carbonyl groups)

27 Na+NH2 - Vinyl halide to alkyne Heat

Dehydrohalogenation.
28 H2O /dilH2SO4 Alkynes  vinyl alcohol Hg2+/333K
 carbonyl compounds
(acetaldehyde or ketones)
due to tautomerism

Hydration of alkynes
29 Mixture of conc.HNO3 and Benzene to nitrobenzene 323 to
conc.H2SO4 333K

Nitration (Electrophilic substitution reaction)

Nitronium (NO2+) ion is the electrophile

Aniline to mixture of 100C

nitroanilines
30 Halogen (Chlorine or Halogenation of benzene Room
Bromine) temp

Anhydrous AlX3 is the catalyst

Halonium (X+) ion is the electrophile
31 Fuming sulphuric acid Benzene to benzene 250 C
H2SO4(SO3) sulphonic acid

Sulphonation
SO3 is the neutral electrophile
32 Alkyl halide Benzene to alkyl benzene

Friedel Crafts alkykation

Alkyl carbocation is the electrophile
With n-propyl chloride, the product is isopropyl
benzene (cumene). Because, n-propyl
carbocation(primary carbocation) converts to more
stable isopropyl carbocation(sec carbocation).
33 Acyl halide Benzene to acyl benzene Heat

Friedel Crafts acylation

Acyl carbocation is the electrophile
(Acetic anhydride and ethanoyl chloride will give
same product – Acetophenone ( 1-Phenyl
ethanone).
34 Cl2 Benzene to Benzene UV
hexachloride (gammaxene) radiation/5
00K

Free radical Addition reaction.

35 Cl2 Benzene to Anhydrous
hexachlorobenzene AlCl3 /
dark ,cold

Electrophilic substitution reaction

36 HCl/ZnCl2 Primary and secondary Heating It is a nucleophilic substitution reaction.
alcohols to alkyl chlorides
37 HCl (no catalyst required) Tertiary alcohols to alkyl Room temp It is a nucleophilic substitution reaction.
chlorides.
38 HBr (48%) Alcohol to alkyl bromide Constant It is a nucleophilic substitution reaction.
boiling The order of reactivity of alcohols with a given
haloacid is 3°>2°>1°
39 NaI or KI in 95% H3PO4 Alcohol to alkyl Iodide Heating It is a nucleophilic substitution reaction.

40 PX3 Alcohol to alkyl halide Heating

Carboxylic acid to acid Heating

halide
41 PX5 Alcohol to alkyl halide Heating

Carboxylic acid to acid Heating

halide
42 SOCl2 Alcohol to alkyl chloride Heating
Carboxylic acid to acid Heating
chloride
Pure form of product is obtained as the gaseous
byproducts escape
43 Red P/X2 ( X= Cl or Br) Alcohol to alkyl halide Heating

Carboxylic acids to
α-halo acids Heating

Hell-Volhard-Zelinsky reaction
44 NaI in dry acetone Preparation of alkyl iodides Heating
from alkyl chlorides/
bromides

Halogen exchange reaction

45 AgF, Hg2 F2 , CoF2 or Preparation of alkyl Heating
SbF3 fluorides from alkyl
chlorides/ bromides
Swarts reaction , Halogen exchange reaction
46 NaNO2 /HCl Conversion of aniline to 00-50 C
benzene diazonium
chloride

Diazotization
 Diazonium cholride into
CuCl,CuBr,CuCN, Chlorobenzene, Bromo
benzene, Benzonitrile,

Iodo Benzene , Phenol,

KI,H2O, H3PO2 or Ethyl Benzene respectively
alcohol

Diazonium Chloride into

HBF4 Floro Benzene

Aliphatic primary amines

NaNO2 /HCl to alcohols

Aliphatic primary amines give unstable diazonium

salts which on hydrolysis yield alcohol with the
liberation of N2 (Quantitative evolution of nitrogen
is used in estimation of amino acids and proteins).
47 Aq.KOH Alkyl halide to alcohol

Nucleophilic substitution reaction.

48 Alkyl halide to ether Room

NaOR (sodium alkoxide ) temp
Nucleophilic substitution reaction.
Sodium ethoxide acts as a Williamson synthesis.
nucleophile when the
reaction occurs in
aqueous conditions
without heat.
49 NH3 Alkyl halides to primary
amines
RNH2 Alkyl halides to sec.
amines
RNHR’ Alkyl halides to tert.
amines
RN(R’)R” Alkyl halides to quaternary
ammonium salts

NH3 Carboxylic acids to amides

50 KCN Alkyl halides to nitriles

Nucleophilic addition

Aldehydes or ketones to
cyanohydrins
51 AgCN Alkyl halides to isonitriles R-X + AgCN  RNC + AgX

52 KNO2 Alkyl halides to alkyl R-X + KNO2  RONO + KX

nitrites
53 AgNO2 Alkyl halides to R-X + AgNO2  RNO2 + AgX
nitroalknanes
54 R’COOAg Alkyl halides to esters R-X +R’OCOAg  R-OCOR’ + Ag X
55 Alkyl halides to alkanes R-X + LiAlH4  RH
Aldehydes to Primary LiAlH4 + RCHO  RCH2OH
alcohols
Ketones to secondary LiAlH4 + RCOR’  R(‘R) CHOH
alcohols
Carboxylic acids to LiAlH4 + RCOOH  RCH2OH
LiAlH4 primary alcohols
Esters to primary alcohol LiAlH4 + RCOOR’  RCOOH + HOR’
Amides to amines LiAlH4 + RCONH2  RCH2NH2
Nitriles to amines LiAlH4 + RCN  RNH2
Acid halide to Primary LiAlH4 + RCOCl  ROH
alcohol
Alkyl isocyanides to LiAlH4 + RNC  RN(H)CH3
secondary amines
56 B2H6 followed by Alkenes to alcohols (anti
( H2O2/OH-) Markovnikov’s product)
57 Aldehydes to Primary NaBH4 + RCHO  RCH2OH
alcohols
NaBH4 Ketones to secondary NaBH4 + RCOR’  R(‘R) CHOH
(Note: NaBH4 can not alcohols
reduce C=C, R-X, R-NO2 , Acid halide to Primary NaBH4 + RCOCl  ROH
R-CN , RCOOH and acid alcohol
derivatives)

58 1.Formaldehyde to primary
alcohol
2.Any other aldehyde to
secondary alcohol
3.Ketones to tertiary
RMgX ( Guignard reagent) alcohol.
4.HCN to aldehyde
5.Nitriles to ketones
6.With CO2 to carboxylic
acids
7.Epoxide to primary
alcohol.
59 (CH3CO)2O / H+ Alcohol/Phenol to O-acyl
CH3 CO-Cl/ Pyridine phenol

Aniline to N-acyl aniline.

Acylation of Alcohols/ phenol or aniline

60 CHCl3/Ethanolic KOH Primary amines to
isocyanides
Carbylamine reaction, Isocyanide test.
61 CHCl3/Aq.NaOH Phenol to o-hydroxy Heat
benzaldehyde (+ little
amount p -isomer)

Reimer-Tiemann reaction
62 Pyridinium 10 alcohol to aldehydes
ChloroChromate (PCC), a
complex of chromium
trioxide with pyridine and
HCl
20 alcohol to ketones

Or
Pyridinium salt of
dichromate (PDC)

or
CrO3 anhydrous

Cu at 573K Apart from above two

conversions,
30 alcohol to alkene

CrO3 / Acetic anhydride Toluene to benzaldehyde

(Ac2O)

63 Conc. HCl + Anhyd. ZnCl2 30 alcohols react

(Lucas reagent) immediately to form 30
alkyl halide.

20 alcohols react slowly to

form 20 alkyl halide.

10 alcohols do not react

appreciably at room
temperature
64 SnCl2 + HCl Nitriles to aldehydes

Stephen reduction
65 Diisobutylaluminium Nitriles to aldehydes
hydride, (DIBAL-H)
Esters are also reduced to
aldehydes
66 CrO2Cl2 Toluene to benzaldehyde

Etard Oxidation
67 CO + HCl Benzene to benzaldehyde Anhydrous
AlCl3
catalyst

Gatterman – Koch formylation

68 HCN Aldehydes or ketones to
cyanohydrins

69 NaHSO3 Aldehydes give adducts

( ketones are less reactive)

This reaction is useful for the separation and

purification of aldehydes.
70 ROH / HCl gas Aldehydes or ketones to
hemi acetals ( hemi ketals )
and acetals (ketals)

ROH /H+ Carboxylic acids to esters

71 NH3 and its derivatives Aldehydes or ketones form

corresponding
condensation products
72 Zn-Hg / HCl

Clemmensen reduction
73 NH2-NH2 and KOH/ Heat
Ethylene glycol
Wolff-Kishner reduction
74 Ammoniacal silver nitrate Test to identify aldehydes Heat
solution (Tollens’ reagent), Silver mirror test
75 Fehling’s test Test to identify aliphatic Heat
(Fehling reagent comprises aldehydes
of two solutions, Fehling
solution A is aqueous
copper sulphate and
Fehling solution B is
alkaline sodium potassium
tartarate (Rochelle salt).
76 NaOH /X2 Compounds with acetyl Heat
(NaOX) group (also EtOH and
X= Cl or Br or I Isopropanol) will yield
haloform
Haloform reaction
77 Dil NaOH or Ba(OH)2 Aldehydes or ketones with Heat
α- hydrogens to aldol

Aldol condensation
78 Conc NaOH (or KOH) Aldehydes or ketones Heat
without α- hydrogens form
acid and alcohol
(disproportionation)

Cannizzaro reaction.
79 Br2 / Aq. Or ethanolic Amides to amines with one Heat
NaOH carbon less than starting
material
Hoffmann Bromamide reaction
80 H2O/H+ Cyanides to amides to Heat
carboxylic acids,

Esters into carboxylic acis

and alcohols,

Acid chlorides or
anhydrides into carboxylic
acids

81 Sn / HCl Nitrobenzene to anilne

Or
Fe /HCl
82 Benzenesulphonyl chloride 10 and 20 amines to
corresponding sulphonyl
amides

Hinsberg Reagent
Sulphonyl amide of 10 amine soluble in KOH due
to acidic hydrogen

30 amines will not react

Sulphonyl amide of 20 amine without acidic
hydrogen, insoluble in KOH
83 P4O10 or P2O5 Dehydration of acids into
anhydride,

Amides into nitriles

84 KOH /RX Phthalimide into aliphatic

primary amine

Aromatic primary amines cannot be prepared by

this method because aryl halides do not undergo
nucleophilic substitution with the anion formed by
phthalimide.
Gabriel phthalimide synthesis.
85 Br2 /H2O Phenol to 2,4,6-
tribromophenol

Aniline to 2,4,6-
tribromoaniline

86 Br2/ CH3-CO-Cl Aniline into 4-

/(CH3CO)2O bromoAniline
87 HNO3 + H2SO4/CH3-CO- Aniline into 4-nitroaniline
Cl /(CH3CO)2O

88 Benzene diazonium Conversion phenol /

chloride (Electrophile) aniline to p-hydroxy
azobenzene/p-
aminoazobenzene

Diazocoupling ( electrophilic substitution)