ORGANIC CHEMISTRY This reaction follows first order kinetics.
1. Predict the alkenes that would be formed in the
following reactions and identify the major alkene.
Ans:
According to Saytzeff’s rule.
(ii)
2. How will you carry out the following
conversions?
1) Ethane to bromo ethene
2) Toluene to benzyl alcohol
Ans:
1) Ethane to bromo ethene:
2) Toluene to benzyl alcohol:
3. Explain the mechanism of Nucleophilic
unimolecular substitution SN1 reaction with one
example.
 The rate of SN1 reaction depends only on the
concentration of alkyl halide.
R α [R–X]
R = k [R–X]
 SN1 reaction is two step mechanism
(i) In 1st step alkyl halide undergo ionization and form
a carbocation.
(ii) In 2nd step the carbocation combine with
nucleophile gives product.
Ex:
 The order of reactivity of SN1 reaction is 30 > 20 >10
alkyl halides
4. Explain the mechanism of Nucleophilic
bimolecular substitution SN2 reaction with one
example.
 The rate of SN2 reaction depends upon the
concentration of both alkyl halide and nucleophile.
R α [R–X] [Nu–]
R = k [R–X] [Nu–]
 This reaction follows second order kinetics.
 SN2 mechanism is one step mechanism.
 In these reactions a transition state formed. In
which both the reactant molecules are partially
bonded to each other.
 The order of reactivity of SN2 reaction is 10 > 20
>30 alkyl halides
5. Define the following (i) Racemic mixture
(ii) Retention of configuration (iii) Enantiomers
(i) Racemic mixture:
 The equimolar mixture (50:50) of dextro and laevo
isomers is called Racemic mixture.
 Racemic mixture has zero optical rotation.
Ex: ( ) butan-2-ol

(ii) Retention of configuration:

 The repetition in stereo chemistry of the reactant, in
8. Write the equations for the preparation of
the product is known as Retention of configuration.
Phenol using benzene, conc.H2SO4 and NaOH.
 If the product formed has configuration opposite to
that of the reactant then the reaction is said to be
inversion of configuration.

9. Explain the acidic nature of phenols and

(iii) Enantiomers:
The stereoisomers which are non super imposible
mirror images to each other are called enantiomers.
compare with that of alcohols.
Phenols are acidic in nature because they produce
proton and phenoxide ion. The formed phenoxide ion
is stabilized by resonance effect.
More the stability of conjugate base more is acidic in
nature.

6. Write the reactions showing the major and The resonating structures of phenoxide ion
minor products when chlorobenzene is reacted
with CH3Cl and CH3COCl in presence of AlCl3.
(a) Friedel Craft’s alkylation:
Chlorobenzene reacts with CH3Cl in presence of
anhydrous AlCl3 to form 1-chloro-4-methyl benzene
(major) 1-chloro-2-methyl benzene (minor).

Comparision of acidic nature of Phenol and

(b) Friedel craft’s acylation:
Chlorobenzene reacts with CH3COCl in presence of
anhydrous AlCl3 to form 2-chloro acetophenone
(minor) and 4-chloro acetophenone (major)
ethanol:
 Phenol is more acidic than ethanol. This is
because phenoxide ion is more stable than
ethoxide ion due to resonance.
 Resonance is not possible in ethoxide ion hence it
is less stable.

10. Write the products formed by the reduction

and oxidation of phenol.
Reduction: Phenol reacts with Zn dust gives benzene.
7. Give the preparation of phenol from cumene.
Cumene (isopropyl benzene) is oxidized in the
presences of air form cumene hydro peroxide which
on hydrolysis in acid medium gives phenol.
Oxidation: Phenol reacts with chromic acid gives
benzoquinone.
11. With a suitable example write equations for the
following (i) Kolbe’s reaction (ii) Reimer-
Tiemann reaction (iii) Wiliamsons ether synthesis.
(i) Kolbe’s reaction: Phenol reacts with NaOH gives
sodium phenoxide. This reacts with CO2 in acid
medium forms salicylic acid.
(ii) Reimer – Tiemann reaction: Phenol reacts with
chloroform in presence of NaOH gives
salicylaldehyde.
(iii) Williamsons synthesis: Alkyl halides react with
sodium alkoxides to form ethers.
Ex: C2H5Cl + C2H5ONa C2H5–O–C2H5 + NaCl
Diethyl ether
12. Describe the following (i) Acetylation (ii)
Cannizaro reaction (iii) Cross aldol condensation
(iv) Decorboxylation
(i) Acetylation: Anisole reacts with acetyl chloride in
presence of anhydrous AlCl3 gives oand p- methoxy
acetophenone.
(ii) Cannizaro reaction:
Aldehydes which have no α – hydrogen reacts with
concentrated alkali undergo self oxidation and
reduction reaction.
HCHO + HCHO Conc.NaOH CH3OH + HCOONa
(iii) Cross aldol condensation:
Aldol condensation is carried out between two
different aldehydes is called cross aldol condensation.
If both the aldehydes contain α – hydrogen, it gives a
mixture of four products. If only one aldehyde contain
α – hydrogen it gives one product.
(iv) Decarboxylation:
Sodium salts of carboxylic acids heated with soda
lime removal of carbon dioxide takes place in the
form of Na2CO3 is called decarboxylation reaction.
13. Explain the following named reactions.
(i) Sandameyer’s reaction:
Aniline reacts with nitrous acid gives benzene
diazonium chloride which reacts with Cu2Cl2/HCl
gives chlorobenzene.
(ii) Gatterman reaction:
Aniline reacts with nitrous acid gives benzene
diazonium chloride which reacts with Cu/HCl gives
chlorobenzene.
14. Compare the acidic strength of acetic acid,
chloroacetic acid, benzoic acid and phenol.
Ans:
chloroacetic acid > benzoic acid > acetic acid >
Phenol
15. How do you prepare ethyl cyanide and Ethyl
isocyanide from a common alkylhalide?
Ethyl chloride reacts with KCN gives ethyl cyanide as
major product.
CH3–CH2–Cl KCN CH3–CH2–CN+ CH3–CH2–NC
Ethyl cyanide (major) ethyl isocyanide
Ethyl chloride reacts with AgCN gives ethyl
isocyanide as major product.
CH3–CH2–Cl KCN CH3–CH2–NC+ CH3–CH2–CN
ethyl isocyanide (major)
 ORGANIC NAMED REACTIONS heating with KOH in presence of ethylene glycol gives
1. Finkelstein reaction: alkanes.
Alkyl chlorides/ bromides reacts with NaI in presence of
acetone gives alkyl iodides.
Ex: CH3Cl + NaI dry acetone CH3I + NaCl
10. Friedel craft’s Alkylation reaction:
2. Swarts reaction: Anisole reacts with methyl chloride in presence of
Alkyl chlorides/ bromides heated with metal fluorides anhydrous AlCl3 gives o – methoxy toluene and p –
such as AgF, Hg2F2, CoF2 or SbF3 gives alkyl fluorides. methoxy toluene.
Ex: CH3Br + AgF CH3F + AgBr

3. Wurtz – Fittig reaction:

A mixture of alkyl halide and aryl halide reacts with
sodium in presence of dry ether gives alkylarene.
11. Friedel craft’s acylation reaction:
Anisole reacts with acetyl chloride in presence of
anhydrous AlCl3 gives o – methoxy acetophenone and p
– methoxy acetophenone.
4. Fittig reaction:
Aryl halides treated with sodium in presence of dry ether
gives biphenyl.

12. Rosenmund reduction:

5. Kolbe’s reaction: Benzoyl chloride on reduction in presence of Pd –BaSO 4
Phenol reacts with NaOH gives sodium phenoxide. This gives Benzaldehyde.
reacts CO2 gives salicylic acid.

6. Reimer – Tiemann reaction: 13. Etard reaction:

Phenol reacts with chloroform in the presence of Toluene reacts with chromyl chloride gives chromium
NaOH/KOH gives Salicyladehyde. complex, which on hydrolysis gives benzaldehyde. This
reaction is called Etard reaction.

7. Williamson’s reaction:
Alkyl halides react with sodium alkoxides to form 14. Stephen reaction:
ethers. Nitriles are reduced with stannous chloride in the
Ex: Ethyl chloride reacts with sodium ethoxide gives presence of HCl gives imine, which on hydrolysis gives
diethyl ether aldehydes
C2H5Cl + C2H5ONa C2H5–O–C2H5 + NaCl RCN+SnCl2+HCl RCH=NH H3O+ RCHO
Diethyl ether

8. Clemmenson reduction: 15. Aldol condensation:

Aldehydes or ketones react with Zn – Hg and Conc. HCl
gives alkanes.
9. Wolf – kishner reduction:
Aldehydes or ketones react with hydrazine followed by
Aldehydes which having α – hydrogen undergoes
condensation in the presence of dil. NaOH to form β –
hydroxy aldehydes called aldol. Which loses water gives
α, β unsaturated product.
 Aniline reacts with nitrous acid at 0 to 5oC gives
benzene diazonium chloride which reacts with Cu / HCl
gives chlorobenzene.

16. Cannizzaro reaction:

22. Decarboxylation reaction:
Aldehydes which have no α – hydrogen reacts with
Sodium salts of carboxylic acids heated with soda lime
concentrated alkali undergo self oxidation and reduction
removal of carbon dioxide takes place in the form of
reaction.
Na2CO3 is called decarboxylation reaction.
HCHO + HCHO Conc.NaOH CH3OH + HCOONa

17. Cross aldol condensation:

Aldol condensation is carried out between two different
aldehydes is called cross aldol condensation. If both the
aldehydes contain α -hydrogen, it gives a mixture of four
products. If only one aldehyde contain α – hydrogen it
gives one product.
23. Diazotization reaction:
The conversion of primary aromatic amines into
diazonium salts is known as diazotization.

18. Hell – volhard – zelensky reaction (HVZ):

Carboxylic acids having at least one α-hydrogen reacts
with X2 (Cl2/Br2) in presence of red phosphorus to give α
– halo acid. This reaction is called HVZ reaction.
EX: Chlorine reacts with acetic acid in the presence of
red Phosphorus to give trichloro acetic acid.

19. Carbylamine reaction or isocyanide test:

Aniline reacts with chloroform in presence of NaOH
gives phenyl isocyanide. This test used to detect primary
amines.

20. Sandmeyer’s reaction:

Aniline reacts with nitrous acid at 0 to 5oC gives
benzene diazonium chloride which reacts with
Cu2Cl2/HCl gives chlorobenzene.

21. Gatterman reaction: