SRI CHAITANYA IIT ACADEMY - VSP

Extra syllabus

Organic Chemistry-1

Name of the Reactants Reagents Intermediate Products Example/Mechanism Remarks

Reaction
Wurtz reaction Alkyl Sodium/dry ether 1) Free radical Alkanes .CH4 cannot be prepared
halides 2) Organo with double . 30 Rx gives alkenes
metallic number of
compound carbons

Wurtz fitting (Alkyl Sodium in dry ether Free radical Alkyl 3 Products (one mixed
reaction halide & aryl benzene product and 2 self
halide) products

Fittig reaction Aryl halides Sodium in dry ether Free radical di phenyls

Ulmann’s Aryl halides Copper ---- di phenyls

reaction

Mixed wurtz Different Na/ dry ether Free radicals Mixture of

reaction alkyl halides alkanes
Internal wurtz Dihalides Na/dry ether Free radical Cyclo 1,2-dihalo alkenes gives
reaction alkanes alkenes

Corey’s House Alkyl R2 CuLi (Gil man’s alkanes 30 RX gives alknes vinyl,
reaction halides reagent) aryl halides cannot used
R in R2CuLi is alkyl or alkenyl or aryl

Kolbe’s Aq.solution Inert electrodes Free radical Hydro disproportionate

electrolysis of Na or K Carbons
salt of
carboxylic
acid
At anode: R-R+CO2
At cathode: H2
Decarboxylation Sodium salt Soda lime Hydro Alkane obtained with one
of Carbon carbon atom less (The
Carboxylic purpose of CaO to keep
acid NaOH dry)
Isomerisation Higher Anhy. AlCl3+HCl gas Isomeric
alkanes at 2000C high pressure alkanes It involves 1, 2
(Brached
alkanes) shift/ group

Aromatization Alkanes Matallic oxides Benzene

with 6-10 Cr2O3/Al2O3 or V2O5, and -
carbons MO2O3 or S or substituted
Se(6000C high Benzene
pressure

Hydro boration Alkenes 1) BH3 or B2H6 Alkyl boranes Alcohols Addition of H2O
oxidation 2) H2O2/OH- according to anti
Markowni –Koff’s rule

Ozonolysis Alkenes & 03/Zn/H2O Ozonide Carbonyl Unsymmetrical alkenes

alkynes compounds gives mixture of Carbonyl
compounds

Borodine- Silver salt of Br2/CCl4 Alkyl

Hunsdisker carboxylic bromides
Order of retn: 10>20>30
reaction acid
Simonini reaction
Finkelstein Alkyl NAI/Acetones Alkyl NaCl and NaBr is
reaction Chlorides or Iodides insoluble in acetone
bromide
Swart reaction R-Cl or R-Br Hg2F2/SbF3/AgF/ Alkyl
Or RI AsF3 fluorides
Sand rayer rectn Benzene *CuCl/HCl Aryl halides
diazonium *CuBr/HBr
chloride (or) Cu2Br2/HBr

Gatter Mann’s Benzene Finely divided Aryl halides

reaction diazonium Cu+HCl or HBr
chloride

Esterification Alcohol H2SO4 or dry HCl gas Esters During esterfication inter
+Carboxylic (If HCl is used as molecular elimination of
acid catalysis) Then this H2O Takes place
rctn is called as fisher
–speler esterification
Organic Chemistry-2

Name of the Reactants Reagents Intermediate Products Example/Mechanism Remarks

Reaction
Reimer – Phenol O - Hydroxy
is an
Thiemann Benzaldehyde
electrophile
reaction

Kolbe’s Phenol (or) - O-hydroxy

reaction Phenoxide benzoic acid

Williamson R-X (No aryl RONa or reaction ether

synthesis halides)

Rosenmunds Acid Alde hydes Ketones cannot

H2+Pd-
reduction chlorides prepared
In the presence of
sulphur
Stephen’s Alkyl imino Chloride Aldehyde Ketones cannot
reduction cyanides prepared

Etard reaction Toluene or Carbonyl Terminal carbon of

alkyl compound alkyl group is
Benzenes (Chromyl converted into -
chloride) CHO
Or

Clemenson’s Aldehydes & Zn-Hg+Conc- - alkanes >C=O converts to-

reduction ketones HCl CH2-

Wolf –Kishner Aldehydes & N2H4+KOH in - Alkanes >C=O converts to-

reaction ketones ethylene glycol CH2-

Bayer villeger Aliphatic H2 SO5 or - Esters Rearrangement

oxidation ketones MCPBA (or) oxidation
Peracetic acid
Cannizzaro’s Aldehydes Conc.NaOH - Alcohol & salt Dispropotionation
reaction with out - of acid (disproportionation) reaction
Hydrogen

Crossed Mixture of Conc.alkoli - Alcohol and More reactive

cannizzaro aldehydes salt of aldehyde oxidised
with out - carboxylic acid
H
Gattermann Benzene or CO+HCl Benzaldehyde
Koch retn its (or) its
derivatives derivatives

Aldol Aldehydes Dil alkali -hydroxly

condensation having - carbonyl unsaturated
Hydrogen compound carbonyl
(or) ketones (carbanion) compound
with - H

Crossed aldol Two differed alkali Carbonion Crossed product

aldehydes unsaturated depends on no of
are ketones carbonyl different
with compounds

One alkali -
aldehyde are unsaturated
ketone with carbonyl
and compound
other with
out
Oxoprocess Alkenes CO+H2 Carbonyl Only aldehydes
compound formed in this
(Straight chain reaction
major)
Halo form Methyl NaOH+Cl2 Halo form Compounds
reaction secondary NaOH+Br2 undergo basic
alcohols/Met NAOH+I2 hydrolysis to
hyl Or produce methyl
Ketones (X2+Na2CO3) 20alcohols or
/Methyl methyl ketones also
aldehydes gives this reaction

Perkin’s Only Acid anhydride -

reaction aromatic and its sodium Unsaturated
aldehyde salt carboxylic acid

Cinnamic acid
Benzoin Only AlC.KCN - hydroxy - hydroxy
condensation aromatic ketones carbonyl comp
aldehydes gives Tollens test

Witting Ketones and Phosphorous Four membered Alkene with In this reaction
reaction aldehydes ylides Betain more number carbonyl carbon
intermediate of carbon convert into
atoms Ethylenic carbon
Beckmann Ketoximes Lewis acid N-alkeyl Anto alky group is
rearrangement H2SO4, P2O5, amindes migrated
PCl5, SOCl2
Micheal Compounds Base Nucleophilic
Reaction having active addition on active
mathylene ethylenic bonds
group are (Ethylene centers
add to with M-groups like
activated –NO2,-CN)
olefinic bond
of the type
Z-
CH=CH2(Z
is EWG)
HVZ reaction Carboxylic Cl2 or Br2 in the Acid chloride halo acids
acids having presence of Red intermediate
-hydrogen phosphorous

Hoffmann Amides Br2/NaOH RNCO 10 amines This is

bromanide rearrangement
degradation reaction
Gabriel Potassium Alkyl halides SN2 10 amines
phthalimide Phthalimide
reaction

Carbylamine Aliphatic CHCl3/KOH R-NC It is identification

reaction (or) aromatic test for 10 amines
10 amines

Diazotisation Aromatic 10 NaNO2+HCl 0- Benenzene

amines 50C diazonium
chloride

Azocoupling Benzene Benzene

diazonium activated
salt compound
P-hydroxy azobenzene (red dye)
Friedel craft Benzene and Alkyl halides Arrheniumion Alkyl benzenes In this reaction
reaction its
substituted
compounds
(Re arranged products also obtained due to
carbocation stability etc not involved

Friedel craft Benzene and Acid halide & Alkyl benzene

acylation its acid an hydride
derivatives ketenes

Meer wein Ketones Aluminium Secondary Ethylene and

pondorf varley isopropoxide in alcohol acetylene centres
reduction the presence of are not effected
isopropyl alcohol

Schmidf Carboxylic N3H/H2SO4 I0 amines Scmidt reaction

reaction acids & obtained with with ketone is
Ketones carboxylic acid similar to
Beckmann
rearrangement

Tisehenko’s All Al(OEt)3 Carboxylic

reaction aldehydes acid + alcohol
+ ester