Organic Phenol, Aniline, Carboxylic Acid

ABC-2, 3 & 4
ABC-2 (Phenol & Aniline)
(A) PHENOL
Preparation of Phenol (5-Methods)
1. Cumene hydroperoxide method CH3 CH3
CH OH
O
This is an industrial process to convert cumene (1) O2 / h
into phenol and acetone in the presence of 


 +CH3–C–CH3
( 2) H3O
oxygen from air followed by hydrolysis. acetone
Phenol
2. Dow's process. Cl OH
(1) NaOH
(2) HCl
In this process chlorobenzene is heated at +NaCl+ H2O
350ºC
350°C (under high pressure) with sodium High pressure
hydroxide which yields phenol. Chlorobenzene Phenol
3. Fusion of Benzene sulphonic acid

SO3H OH
with concentrated NaOH
(1) NaOH/
  

This is commercial process for synthesizing ( 2) H
phenol. Benzene sulphonic acid is melted Benzene Phenol

(fused) with sodium hydroxide at (300°C– Sulphonic acid
320°C) followed by hydrolysis which yields

phenol.
4. Decarboxylation of salicylic acid OH OH

COONa Soda lime
Distillation of salicyclic acid with soda-lime 


produces phenol.
5. Hydrolysis of Benzene diazonium + –

NH2 NN Cl
salt NaNO , HCl
2
Benzene diazonium salt is prepared by reacting H2O, 5ºC
aromatic primary amine with NaNO2, HCl at low
Aromatic Aryl diazonium salt
temperature.Then this aqueous solution is Primary amine
heated to get phenol.
+ –
NN Cl OH
Heat

H2O
Phenol
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ABC-2, 3 & 4 - 1
ABC-2, 3 & 4
Chemical Reactions of Phenol [5-Reactions]

1 (a) Reaction with Br2/H2O OH
OH
When bromine is added to solution of phenol in
   Br
Br2 Br
presence of ethanol or H2O, it forms white precipitate EtOH / H 2 O
+ HBr
of 2,4,6-tribromo-phenol.
Br
White ppt.
(b) Reaction with Br2/CS2 OH

OH OH
In order to add one equivalent of bromine to phenol, Br
Br2, CS2
carbon disulfide (CS2) is used at low temperature and < 5ºC
+
forms para-bromophenol and ortho-bromophenol
Br
2. Reimer Tiemann formylation OH OH OH

Phenol when heated with chloroform and NaOH (1) CHCl / NaOH/
 CHO
followed by H2O forms salicyladehyde.
3
 
  +
(2) H2O
Major CHO
3. Reimer Tiemann carboxylation OH OH OH

COOH
Phenol when heated with CCl4 and sodium hydroxide CCl / NaOH / 
4
    
+

H
followed by hydrolysis forms salicylic acid.
COOH Major
Note: Salicyclic acid can be used in formation of O

aspirin. O–C–CH3
(Aspirin is used as painkiller) OH COOH

Ac 2 CO / H
COOH    
Aspirin
4. Kolbe's Schmidt Reaction OH O–

(i) OH  COO– (iii) HCl
Phenol when reacted with hydroxide ion in presence    
(ii) CO 2
of CO2 forms a complex which on acidification forms
salicyclic acid. OH OH
COOH
+
COOH Major
ABC-2, 3 & 4 - 2
ABC-2, 3 & 4
5. Bakelite formation OH OH OH
CH2O CH2OH
Bakelite is made by condensation reaction between  

NaOH
phenol and formaldehyde.
CH2OH
Polymerises
OH OH
OH OH
Bakelite
Lab test for Phenol

1. Litmus test
Phenol turns blue litmus red. Phenols behave as weak acid because of presence of polar O–H
+
group, they ionise in aqueous solution to give H ions.
OH O
+
+ H2O  H3O
Phenol Phenoxide
ion
2. Neutral FeCl3
Phenols give a violet-coloured water soluble complex with neutral ferric chloride.
+
6 Ph–OH + FeCl3  Fe(OPh)3–6 + 3H + 3HCl
Violet complex
ABC-2, 3 & 4 - 3
ABC-2, 3 & 4
NH2
(B) ANILINE
Preparation of Aniline [3-Methods]

3. Hofmann bromamide
1. Reduction by Metals 2. Reduction by H2
degradation reaction
NO2 NH2 In this reaction an unsubstituted
NH2 amides treated with NaOH/KOH
and bromine to give a primary
Ni / H2 or Pd / H2
amine that has one carbon lesser
Metal / Acid
than starting amide.
NO2 NH2 O
R–C–NH2 + Br2 + 4NaOH
Sn / HCl
+ 6H
R–NH2 + Na2CO3 + 2NaBr + 2H2O
NH2
R can be : Alkyl or phenyl

Fe/ HCl
+ 6H
Special
NO2 NH2
(NH4 )2 S
 
Selective reduction
NO2 NO2
Chemical Reactions of Aniline :
1. Preparation of diazonium salt:
Aniline reacts with NaNO2/H+ to form diazonium salt.
NH2 N2+Cl
–
NaNO2 / HCl
(O–5°C)
Benzene
diazonium chloride
Note :
1. Primary aliphatic amines react with nitrous acid to form aliphatic diazonium salt which being unstable,
liberate nitrogen gas.
2. Primary aromatic amines form arene diazonium salts which are stable for a short time in solution at low
temperatures (273-278 K).Due to its instability, the diazonium salt is not generally stored and is used
immediately after its preparation.
ABC-2, 3 & 4 - 4
ABC-2, 3 & 4
2. Chemical reactions of diazonium salt

Diazonium salt opens the way to prepare many other compounds, see following chart.
ABC-2, 3 & 4 - 5
ABC-2, 3 & 4
1. Complete the following reactions.

NNCl
CuCl/HCl
i. or ii. iii.
Cu2Cl2/HCl
CH3
 
NNCl NNCl
H3PO2 C2H5OH
iv. v. vi.
CH3 CH3

NNCl
H2O, 
vii. viii.
CH3
2. Conversion.

Ph–NO2 Ph–Cl
H2/Pd Sandmayer reaction
NaNO2/HCl
Ph–NH2
Lab test of Aniline :
1. Carbylamine Reaction
Primary amines (aliphatic as well as aromatic) react with chloroform (CHCl3) on heating in the
presence of ethanolic solution of KOH to form isocyanides (also called carbylamines) which are foul
smelling substances. Secondary and tertiary amines do not undergo this reaction, therefore this
reaction is used as a test for primary amines (aliphatic as well as aromatic).
R–NH2 + CHCl3 + 3KOH Heat R–NC + 3KCl + 3H2O

Heat
Ex. CH3–NH2 + CHCl3 + 3KOH CH3–NC + 3KCl + 3H2O
NH2 NC
Heat
Ex. + CHCl3 + 3KOH + 3KCl + 3H2O
ABC-2, 3 & 4 - 6
ABC-2, 3 & 4
2. Azo dye test

Azo compounds are usually intensely colored because of the azo linkage (–N=N–). Azo
compounds, because of their intense color’s and because they can be synthesized from relatively
inexpensive compounds, are used extensively as dyes.
Synthesis of orange-red dye from 2-naphthol [-naphthol] and aniline.
O N=N
H OH
NaNO2/H2SO4 +
NH2 N2
(0–5°C) NaOH pH = 8-10
Orange-red Dye
3. Bromine water Test (Br2 + H2O):

Aniline reacts with bromine water at room temperature to give a white precipitate of
2,4,6-tribromoaniline.
NH2 NH2
Br Br
Br2 / H2O
+ 3Br2 + 3HBr
Aniline Br
2,4,6- Tribromoaniline
ABC-2, 3 & 4 - 7
ABC-2, 3 & 4
ONLY ONE OPTION CORRECT TYPE

1. The process of conversion of cumene in the presence of oxygen and light followed by hydrolysis lead to
the formation of _______ .
(A*) Phenol (B) Aniline (C) Anisole (D) Benzene
vkWDlhtu ,oa izdk'k dh mifLFkfr esa D;wehu ds lkFk vfHkfØ;k dj rRi'pkr~ tyvi?kVu ij izkIr mRikn -----------------
gSA
(A*) fQukWy (B) ,fuyhu (C) ,fulksy (D) cSathu
2. Identify the product of following reaction.
fuEu vfHkfØ;k dk mRikn igpkfu;s&
CH3–CH–CH3
O2 / h
  


H3O
CH3
OH
(A*) (B) (C) (D) None of thesemijksä esa ls dksbZ ugh
CH3 CH3
3. Identify the product of the following reaction.
Cl
( i) NaOH
(ii) HCl
  ______ + NaCl + H2O
350 º C
High pressure
Cl OH OH OH
Cl
(A) (B) (C*) (D)
Cl Cl Cl
Website : www.resonance.ac.in | E-mail : contact@resonance.ac.in ABC–2 - 1

ABC-2, 3 & 4
SO3H
( i) NaOH/
4.   
 ?
( ii) H
CH3
SO3H SO3H OH CH3

OH
(A) (B) (C*) (D)
OH OH
CH3 CH3 CH3
5. Give the product for following reaction.

OH
COONa
Soda lime
  

C 2 H5
OH OH
COOH
(A) (B*) (C) (D) None of thesemijksä esa ls dksbZ ugha
C2H5 C2H5 C 2H5
6. Identify the X and Y in the following reaction.
fuEu vfHkfØ;k esa X ,oa Y dks igpkfu;s&
NH2
NaNO , HCl 
2 X  Y
H2O, 5ºC H2O
+ –
OH N2Cl OH
(A) X = Y= (B) X = Y=
+ –
N2Cl OH N2Cl
(C*) X = Y= (D) X = Y=

ABC-2, 3 & 4
7. What will be the product of following reaction?
fuEu vfHkfØ;k dk mRikn D;k gksxk\
OH
2 Cl
 
EtOH / H2O
OH OH OH OH
Cl Cl Cl
(A) (B) (C) (D*)
Cl
Cl Cl Cl
8. Find the product for the following reaction.
fuEu vfHkfØ;k dk mRikn D;k gksxk\
OH
2 2 Br , Cs
 
 5ºC
CH3
OH OH Br
Br
(A) (B*) (C) (D) None of these mijksä esa ls dksbZ ugh
Br CH3
9. Give the major product for the following reaction.
fuEu vfHkfØ;k dk eq[; mRikn D;k gksxk\
OH
CHCl 3 / NaOH
   

Me
OH OH OH OH
CHO Me COOH
(A) (B*) (C) (D)
CHO Me Me Me

ABC-2, 3 & 4
10. The reagent used for Reimer Tiemann carboxylation in order to form salicylic acid is _______ .
lsfylhfyd vEy ds fuekZ.k ds fy, jhej Vheku vfHkfØ;k esa dkSulk vfHkdeZd iz;qä gksrk gSA
(A) CHCl3 / NaOH / H+ (B*) CCl4 / NaOH / H+
(C) OH– / CO2 / HCl (D) None of these mijksä esa ls dksbZ ugh
11. Aspirin can be formed from following reaction using which reagent?
fuEu vfHkfØ;k esa dkSulk vfHkdeZd ,fLizu ds fuekZ.k esa iz;ksx fd;k tkrk gS\
O
OH O–C–CH3
COOH COOH

O O
+
(A*) (CH3–C–)2O / H (B) (C2H5–C–)2O / H+ (C) CHCl3 / NaOH (D) None of these
mijksä esa ls dksbZ ugh

12. Give product for following reaction.
fuEu vfHkfØ;k dk mRikn crkb;sA

OH
CHCl 3
 
KOH
CHO COOH
CHO OH OH
(A) (B*) (C) (D) None of these
mijksä esa ls dksbZ ugh

13. The reactant used in the reaction is
fuEu vfHkfØ;k esa vfHkdkjd gksxk\

OH
COOH
–
OH / CO2
vfHkdkjd reactant  
HCl

OH
OH OH
COOH
(A) (B) (C*) (D)

ABC-2, 3 & 4
Anilne ,fuyhu
NO2
14. Sn/HCl R is gS&

+ 6H
R,
CH3
NO2 NH2 NH2 NH2
(A) (B) (C*) (D)

CH3 CH3
Cl
NH2
Fe/HCl
15. R + 6H , R is gS&
NO2 NO2 NO2

NO2
(A) (B) (C*) (D)
NH2
Ni/H2
16. R , R is gS&
CH3
NO2 NO2 NO2 NO2
(A) (B*) (C) (D)
CH3
Br2/NaOH
17. R C2H5–NH2 , R is gS&
CH3
(A) C2H5–CH2–C–NH2 (B) C2H5–CH–C–NH2
O O
CH3
(C*) C2H5–C–NH2 (D) C2H5–CC–NH2
O CH3 O

ABC-2, 3 & 4
+
–
N2Cl
H3C CH3
NaNO2/HCl R, is-
18. R (0–5°C)
gS&
CH3
NO2 NH2
H3 C CH3 H3 C CH3 CH3 H3C CH3
(A) (B*) (C) (D)
CH3 CH3 CH3 CH3
19. Which of them produces diazonium cation at 0°C ?
buesa ls fdlds }kjk 0°C ij MkbZ,stksfu;e /kuk;u dk fuekZ.k laHko gSS
NH2 NH–CH3
CH3
(A*) (B) (C) CH3–CH2–NH2 (D) CH3–C–NH2
CH3
+
N2Cl–
P
20. , P is gSa ?
C2H5 C2H5
(A) Cu2Cl2/HCl (B) Cu/HCl (C*) C2H5OH (D) HBF4
NC
CHCl3 + 3KOH/
21. R R is - gSa ?
C2H5

–
N2Cl NO2
(A) (B)
C 2H 5 C2 H5
NH2 CN
(C*) (D)
C2 H5 C2 H5

ABC-2, 3 & 4
OH
NO2
H2/Pd NaNO2/HCl
22. (A) (B) NaOH (pH=8-10)
(C)
(0-5°C)
SO3H
C is gSa -
+ –
(A) HO3S O N2Cl (B*) HO N=N SO3Na
+ – + –
(C) HO N2Cl (D) HO SO2 N2Cl
OH
NH2
NaNO2/H2SO4 CH3
23. (A) NaOH (pH=8-10)
(B)
(0-5°C)
(A) NH2 O CH3 (B) NH2 CH2 OH
OH
OH
(C*) N=N (D) N=N

CH3
CH3

ABC-2, 3 & 4
ABC-3 (Carboxylic acid & Carbonyl Compounds)
(A) CARBOXYLIC ACID

 Compounds containing the carboxyl group (–COOH) are distinctly acidic and called carboxylic acid.
Compound Common name IUPAC name Occurrence
HCOOH Formic acid Methanoic acid Ants, bees & other stinging insects.
CH3COOH Acetic acid Ethanoic acid Grapes, Vinegar & pickle
Animal fats, vegetables fats

CH3–CH2–COOH Propionic acid Propanoic acid
(coconut oil.)
CH3–(CH2)2–COOH Butyric acid Butanoic acid Rancid butter
COOH
Oxalic acid Ethanedioic acid Kidney stone, Cabbage
COOH
COOH
CH2 Malonic acid Propanedioic acid Plants (Leaves of lucerne)
COOH
CH2–COOH
Succinic acid Butanedioic acid Amber, Lignite and many plants
CH2–COOH
COOH
Benzoic acid Benzene carboxylic acid Cranberries, fruit juice, soft drink, plum
Preparation of Carboxylic acid (3-Methods)

1 By Grignard reagents : O
1. CO2 , Et 2O
(i) CH3–CH2–MgCl     CH3–CH2–C–OH
O 2. H3O
1. CO2 , Et 2O
R – MgX     R–C–OH
Grignard reagent 2. H3O Carboxylic acid
MgBr COOH
1. CO2 , Et 2O
(ii)    
2. H3O
(i) Carbon dioxide is a carbonyl compound and

it is an electrophile.
(ii) X is (Cl, Br, I)
(iii) Alkyl magnesium halide [R–MgX] is called
Grignard reagent.
ABC-2, 3 & 4 - 13
ABC-2, 3 & 4
2 By Oxidation of primary alcohol & (i ) KMnO 4 , O H


R–CH2–OH     R–COOH

aldehydes: 
(i) Primary alcohol and aldehydes are readily (i) KMnO , H 

R–CHO   4 R–COOH

oxidized to carboxylic acids with common

(i) K 2Cr2O7 , H
oxidizing agents such as potassium (i) CH3–CH–CH2–OH  CH3–CH–COOH
permanganate (KMnO4) in neutral, acidic or CH3 CH3
alkaline medium or potassium dichromate 
(ii) CH2–OH 
CrO3 , H
 COOH
(K2Cr2O7) and chromium trioxide (CrO3) in
acidic medium. O O
(ii) Number of carbon atom in carbon chain C–H C–OH
KMnO 4 , H
remains same during oxidation. (iii)   
3 By Hydrolysis of acid derivatives: O O

+
H2O / H
A. Hydrolysis of ester: A.(i)CH3–C–OCH2CH3 CH3–C–OH +CH3–CH2–OH
O O O O
H2O / H+ 18 H2O / H+ 18
R–C–OR' R–C–OH + R'–OH (ii) C6H5–C–OC2H5 C6H5–C–OH + C2H5–OH
B. Hydrolysis of Amides: O O
O C C +
H O / H + NH4
B.(i) CH3 NH2 2  CH3 OH
C 
R NH2 H2O / H
 

O O
H2 O / H +
O (ii) Ph–C–NHPh  Ph–C–OH + PhNH3

+
C + NH4
R OH O O
H2 O / H
Amides undergo hydrolysis when they are C.(i) CH3–C–Cl  CH3–C–OH+ HCl
heated with aqueous acid. O O

(ii)CH3– CH–C–Cl  CH3– CH–C–OH + HCl
H2 O / H
C. Hydrolysis of acid chloride:

CH3 CH3
O O
 O O O
H2 O / H
R–C–Cl   R–C–OH + HCl H2 O / H
D. (i) CH3–C–O–C–CH3   2CH3–C–OH
Acid chloride reacts with water to form

O O O O
carboxylic acid. (ii) Ph–C–O–C–CH3 H O /H
2

Ph–C–OH +CH3–C–OH

D. Hydrolysis of acid anhydride:

E.
O O O
2 H O / H O
R–C–O–C–R  2R–C–OH
(i)CH3–CH2–CH–CN  CH3–CH2–CH–C–OH H2O / H
CH3 CH3
E. Hydrolysis of nitriles:
O
O H2 O / H +
+ (ii) Ph–CH2–CN   Ph–CH2–C–OH + NH4
R–CH2–CN 
H2 O / H
 R–CH2–C–OH + NH4

ABC-2, 3 & 4 - 14
ABC-2, 3 & 4
Chemical Reactions of Carboxylic Acid [5-Reactions]

1 Hell-Volhard-Zelinski reaction (HVZ reaction): Examples
(i) In this reaction a carboxylic acid is treated with O O
(i) PBr3 ,Br2
PX3 and X2, then halogenation at the -carbon (i) CH3–CH2–C–OH  CH3–CH–C–OH
(ii) H2 O
occurs. Br
(ii) X is (Cl, Br). O O

(ii) CH2–C–OH 3(i) PBr ,Br
2 CH–C–OH
O O  
(ii) H2 O
(i) PX3  or red P , X2 Br
R–CH2–C–OH   R–CH–C–OH
(ii) H2O
X
2 Preparation of Acid derivatives: A.
A. Reaction with SOCl2 O O

(i)CH3–CH2–C–OH  CH3–CH2–C–Cl
SOCl2 + SO2 + HCl
O O 

2 SOCl
R–C–OH   R–C–Cl + SO2 + HCl O O

SOCl2
OH  Cl +SO2+ HCl
(ii) 

B.
O O O
+ –
(i)CH3–C–OH + NH3 
CH3–C–ONH4  CH3–C–NH2
B. Reaction with NH3 (ii)

O O O O
– – +
+ CH2 C ONH4
R–C–OH + NH3 R–C–ONH4   CH2–C–OH + NH3
O
R–C–NH2 + H2O O

Carboxylic acid reacts with aqueous ammonia to  CH2 C NH2
form ammonium salts and after heating produce an

C.
amide.
O O
(i)CH3–C–OH + H–O–C–CH3
O O
P2O5, 
CH3 C O C CH3+ H2O
C. Reaction with RCOOH: O
O O O C
CH2–COOH CH2
P2O 5,   (ii)  O + H 2O
2R–C–OH R C O C R + H 2O CH2–COOH CH2 C
P2O5 is a dehydrating agent (removal of H2O). O
D.
O
(i) H+
CH3–CH–CH2–C–OH + C2H5OH
CH3
O
CH3–CH–CH2–C–OC2H5 + H2O
CH3
ABC-2, 3 & 4 - 15
ABC-2, 3 & 4
D. Reaction with R–OH (ii)
O O O O
R'OH, H+ H+
R–C–OH R C–OR' + H2O Ph–C–OH + CH3OH Ph–C–OCH3 + H2O
Carboxylic acid reacts with excess alcohol in the

presence of an acid catalyst produce ester. This
reaction is called fisher esterification reaction.
3 Hunsdiecker Reaction: O
(i) Ag O
(i)CH3–CH2–CH2–C–OH 
2

(i) A carboxylic acid can be decarboxylated if a (ii) Br2 , 
heavy metal salt of the carboxylic acid is heated CH3–CH2–CH2–Br

+ CO2 + AgBr
with bromine.
O
 Ph–CH2–CH2–Br
(i) Ag2 O

(ii) The product is an alkyl halide with one less (ii)Ph–CH2–CH2–C–OH (ii) Br2 ,  + CO2 + AgBr
carbon than the starting carboxylic acid. O

C–OH Br
(iii) The heavy metal can be silver ion or mercuric (i) Ag O
(iii) 2
  + CO2 + AgBr
(ii) Br2 , 
ion.
2 (i) Ag O
R–COOH   R–Br + CO2 + AgBr.
(ii) Br2 , 
4 Sodalime Decarboxylation: O
NaOH  CaO
 CH3 – CH3 + CO2
(i)CH3–CH2–C–OH 
O 
NaOH  CaO
R–C–OH  R–H + CO2
 COOH
 NaOH  CaO
(ii) 
 + CO2

(i) Sodalime: NaOH + CaO
NaOH  CaO
(ii) Decarboxylation simply means removal of CO2. (iii) Ph – CH2 –COOH   Ph – CH3 + CO2

5 Kolbe's electrolysis: (i) 2CH3–COOK + 2H2O 

Electrolysis

CH3–CH3 + 2CO2 + H2 + 2KOH

Electrolysis
2RCOOK + 2HOH  R–R + 2CO2 + H2 + 2KOH
CH2–COOK CH2
Electrolysis
If n is the number of carbon atoms in the salt of (ii) + 2H2O   + 2CO2 + H2 +
CH2–COOK CH2
carboxylic acid, the alkane formed has 2(n–1) 2KOH
carbon atoms. (iii) 2CH3–CH2–COOK + 2H2O 

Electrolysis

CH3–CH2–CH2–CH3 + 2CO2 + H2 + 2KOH
ABC-2, 3 & 4 - 16
ABC-2, 3 & 4
Lab Test of Carboxylic Acid [3-Tests]

1 Sodium bicarbonate (NaHCO3) test :
All carboxylic acids & sulphonic acids give. (i) Ph–COOH + NaHCO3 PhCOONa + H2CO3
R–COOH + NaHCO3  R–COONa + H2CO3 H2O + CO2
(ii)CH3–SO3H + NaHCO3 CH3SO3Na + H2CO3

H2O + CO2
H2O + CO2
R–SO3H + NaHCO3  R–SO3Na + H2CO3
H2O + CO2
Exception :
Picric acid gives NaHCO3 test.
Note : Phenol does not give NaHCO3 test.
2 Litmus test: Acid converts blue litmus into red litmus.

H+
3 Esterification of acid: When carboxylic acid reacts RCOOH + R' OH RCOOR' + H2O
with alcohol then ester forms, which are sweet (fruity) (sweet smelling liquid)
smelling liquids.
ABC-2, 3 & 4 - 17
ABC-2, 3 & 4
(B) CARBONYL COMPOUNDS

Preparation of Carbonyl Compounds (4-Methods)
1. By reduction of acid halide
Reagents H2 / Pd (BaSO4 )
  CH3–CHO
(i)Lindlar’s catalyst : [H2/Pd (CaCO3, quinoline)]
(ii)Rosenmund catalyst : [H2/Pd (BaSO4, quinoline)]
General Reactions
H2 / Pd (BaSO4 )
 
H2 / Pd (CaCO3 ,quinoline)

 R–CHO
2. By oxidation of alcohol using PCC:

Reagents
PCC* = (Pyridinium Chloro Chromate) in CH2Cl2 CH3CH2OH CH3CHO
PCC
Ethanol  Acetaldehyde
Non aquous solvent
+HCl+CrO3 
 .Cl–.CrO3 PCC
CH3–CH–CH3  CH3–C–CH3
OH O
General Reactions
Propan-2-ol Propanone
PCC
R–CH2–OH  RCHO
Aldehyde CH3
PCC
 No reaction
 R–C–R
PCC
R–CH–R  CH3–C–CH3 
OH O OH
Ketone 2-Methylpropan-2-ol
R
PCC
R–C–R  No reaction Note : 3º alcohols don't oxidize by most of the
oxidizing agents
OH
3. By Stephen's reduction of cyanide : (i ) SnCl2 / HCl

CH3–CN    CH3–CH=O + NH4Cl
(ii ) H2O
Reagents : (i) SnCl2/HCl (ii) H2O
General Reactions Ethanenitrile Ethanal
(i ) SnCl2 / HCl (i ) SnCl2 / HCl

R–CN    R–CH = O + NH4Cl Ph–CN    Ph–CH=O + NH4Cl
(ii ) H2O (ii ) H2O
Benzene carbonitrile Benzaldehyde
4.
Dry distillation of calcium salt of fatty acids : (c) By dry distillation of calcium acetate
formate:
(a) By dry distillation of calcium formate :
O
H–C–O
O Dry distillation
Ca    CH3–C–H
H–C–O CH3–C–O – CaCO3
Dry distillation
Ca    
 H–C–H O
H–C–O – CaCO3 O
O
O
ABC-2, 3 & 4 - 18
ABC-2, 3 & 4
(b) By dry distillation of calcium of Acetate : (d) By dry distillation of calcium acetate and
calcium formate :
O
CH3–C–O Dry distillation O O
Ca    CH3–C–CH3
CH3–C–O – CaCO3 CH3–C–O O–C–H
O Ca + Ca
O CH3–C–O O–C–H
O O
Dry distillation –CaCO3
CH3–C–CH3 + H–C–H + CH3–C–H

O O O
Chemical Reactions of Carbonyl Compounds (4-Reactions)

1. Cannizzaro reaction:
Simple Cannizzaro reaction

Aldehydes which do not have an
-hydrogen atom, undergo self
oxidation and reduction
(disproportionation) reaction on
treatment with a concentrated alkali.
Crossed Cannizzaro reaction

On using two types of carbonyl
compounds not having -hydrogen
atom, acid salt will be corresponding
to that aldehyde or ketone which is less steric more steric
less sterically crowded and another crowding crowding
will give alcohol.
2. Aldol condensation (or aldol H H

reaction): H  
(i ) dil. NaOH
Aldehydes and ketones with atleast CH3–C=O + CH–C–H    CH3–C=CH–C–H
H (ii ) 
one -hydrogen undergo a reaction in O O
the presence of dilute alkali as , -unsaturated
catalyst. carbonyl compound
H 3C H 3C
H  
  CH3–C=CH–C–CH3
(i ) dil. NaOH
CH3–C=O + CH–C–CH3 
H (ii) 
O O
, -unsaturated
carbonyl compound
Prediction of reactant (i ) dil. NaOH
 
C=O + CH3–C–H    C=CH–C–H
(ii ) 
O H O
O
H
ABC-2, 3 & 4 - 19
ABC-2, 3 & 4
3. Perkin reaction:
When aromatic aldehyde like (CH3CO)2O / CH3COONa
benzaldehyde is treated with Acetic Sodium acetate
anhydride in the presence of sodium anhydride (Acts as base)
salt of acid from which anhydride is
derived we get -unsaturated acid.
Prediction of reactant
CH = CH–COOH
CH=O (CH3CO)2O H
 +
CH3COONa O
H
Benzaldehyde
Benzaldehyde
4. Reaction with NH2OH CH3 CH3 OH
C=O + NH2–OH 
 C=N
C= O + H2 N–OH H – H2O H
Aldehyde / Ketone
 OH
 C=N
– H2O
Oxime
Aldehyde  Aldoxime
Ketone  Ketoxime
Test for carbonyl compounds

1. 2,4-DNP¼2,4-Dinitrophenyl hydrazine+½Test : CH3
C=O + H2N–NH NO2
Carbonyl compouds (all aldehydes and ketones) H
give yellow–orange precipitate with 2,4–DNP. It is NO2
also knwon as Brady’s reagent. 2, 4-DNP
General Reactions
CH3
C=O + H2N–NH NO2 C=N–NH NO2
H
NO2 NO2
(yellow–orange precipitate of Hydrazone)
2, 4-DNP
CH3
C=O + H2N–NH NO2
C=N – NH NO2 CH3
NO2
NO2
2, 4-DNP
CH3
C=N–NH NO2
CH3
NO2
ABC-2, 3 & 4 - 20
ABC-2, 3 & 4
Test for Aldehydes

1. Tollen’s Reagent [AgNO3 + NH4OH or O
||
{Ag(NH3)2} OH ] :
+  AgNO  NH OH
CH3–CH=O 

 CH3– C – O + Ag  3 4
Tollen’s Reagent gives silver mirror or Black silver mirror

precipitate with aldehydes.
General Reactions O
O ||
|| AgNO3  NH4 OH 
AgNO3  NH4 OH  PhCHO   Ph – C – O + Ag 
R–CH=O   R – C – O + Ag  silver mirror
silver mirror
Note : HCOOH also gives this test. O
||
AgNO3  NH4 OH 
HCOOH   H – C – O + Ag 
silver mirror
2. Fehling or Benedict test (Cu2+ in basic

medium) % O
||
Aliphatic aldehyde gives red precipitate of Cu2O CH3 CH3– C – O 
with Fehling/Benedict solution. Cu2+ reduced into
Cu1+and aldehyde oxidised into acid salt.
O
General Reactions ||
C2 H5 C2 H5 – C – O 
* Aromatic aldehydes do not give this test.

* Schiff reagent is also use for lab test of
aldehyde.
Iodoform Test
Reagents : I2 + NaOH or NaOI (Where R = H,
alkyl, aryl group)
Acetaldehyde, all methyl ketones & ethyl alcohol
give Iodoform test.
General Reactions
ABC-2, 3 & 4 - 21
ABC-2, 3 & 4

dsoy ,d lgh fodYi çdkj (ONLY ONE OPTION CORRECT TYPE)
PART-A (CARBOXYLIC ACID) ¼dkckZsfDlfyd vEy½
1. MgBr 1. CO2,Et2O Product is –
2. H3O
MgBr 1. CO2,Et2O mRikn gS %

2. H3O
COOH
COOH
(A) (B) (C*) COOH (D)
COOH
1. CO2, Et2O COOH

2. A A is gS&
2. H3O
MgBr
(A) (B*) MgBr (C) (D)
MgBr MgBr
K2Cr2O7/H
3. Ph–CH2–OH + Product is - mRikn gS&
O
(A) Ph–CH2–COOH (B) Ph–CH–CH3 (C*) Ph–COOH (D) Ph–CH2–O–C–CH3
COOH
CH2–OH
+
K2Cr2O7/H
4. Find product is – vafre mRikn gS&
COOH COOH
(A) COOH (B) (C) (D*)
COOH
OH
+
CrO3/H
5. Product is - mRikn gS&
CH3
OH
COOH
COOH
(A*) (B) (C) (D)
CH3 CH3 COOH COOH
Corporate Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.)-324005 1
ABC–3 - 1
ABC-2, 3 & 4
O
+
H2O/H
6. C2H5–C–OCH3 Product is - mRikn gS&
(A) CH3COOH, C2H5OH (B) CH3COOH,C2H5–COOH

(C*) C2H5–COOH, CH3OH (D) CH3OH, C2H5–OH
O
H2O/H+
7. CH3–C–NH–Ph A+B

A rFkk B gS&
A & B are -
O O
(A) Ph–NH–C–H + CH3 –COOH (B) CH3–C–NH2 + Ph–OH
O O
+
(C) CH3–C–NH2 + Ph–COOH (D*) CH3–C–OH + Ph–NH3
O O
+
H2O/H
8. C2H5–C–O–C–Ph A+B
Ratio of A and B is –
A rFkk B dk vuqikr gS&
(A) 1 : 2 (B) 2 : 1 (C*) 1 : 1 (D) 2 : 3
+
CN H2O/H
COOH
(A) (B)
COOH
COOH
(C*) COOH (D)
Chemical reaction of Carboxylic acid

dkcksZfDlfyd vEy dh jklk;fud vfHkfØ;k,sa%
Red P  Br2
10. CH3CH2CH2COOH    CH –CH –CH–COOH
3 2
Br
This reaction is called -
(A) cannizzaro reaction (B) Aldol reaction
(C*) HVZ reaction (D) Reimertiemann reaction
Red P  Br2
CH3CH2CH2COOH    CH –CH –CH–COOH
3 2
Br
;g vfHkfØ;k dgykrh gS&
(A) dSfutkjks vfHkfØ;k (B) ,YMkWy vfHkfØ;k
(C*) HVZ vfHkfØ;k (D) jkbej fVeku vfHkfØ;k
ABC–3 - 2
ABC-2, 3 & 4
COOH SOCl2

O
O
C
(A) (B*) C (C) COOH
H (D)
Cl Cl
Cl Cl
COOH 
12. + NH3 Product is- mRikn gS&
O O
(A) (B*)
C–O–NH2 C–NH2
COOH
NH2
(C) (D)
COOH
NH2
COOH

13. Product is- mRikn gS&
COOH
O
C O
O
(A) (B) O (C) O=C O=O (D*) O
C
O
(i) Ag2O
14. Ph–CH–CH–COOH (ii) Br2, 
Product is- mRikn gS&
CH3 CH3
Br
(A) Ph–CH–CH–CH2–Br (B) Ph–CCH–CH3
CH3 CH3 CH3 CH3
(C*) Ph–CH–CH–Br (D) Ph–CH–CH2
CH3 CH3 CH3 CH2–Br
COOH (i) Ag O
2
15. Product is- mRikn gS&
(ii) Br2, 
Br
Br
COOH
(A) (B) COOH
Br
(C*) (D) C–Br
O
ABC–3 - 3
ABC-2, 3 & 4
COOH NaOH + CaO

16.  Product is- mRikn gS&
COOH
(A) (B*) (C) (D)
KOOC
COOK
17. Kolbe electrolysis
+ H2O Product is-
KOOC
COOK
KOOC
COOK
dksYcs oS|qr vi?kVu
+ H2O mRikn gS&
KOOC
COOK
CH3
(A*) (B)
COOH
(C) CH3 C CH3 (D) CH3 CH3

O
Lab test of carboxylic acid:

dkcksZfDlfyd vEy dk izk;ksfxd ijh{k.k
18. CH3–CH–CH2–SO3H + NaHCO3 Product is - mRikn gS&

CH3
(A) CH 3–CH–SO3Na (B*) CH3–CH–CH2–SO3Na + CO2
CH3 CH3
SO3Na
(C) CH3–CH–SO3Na (D) CH3–C–CH3

CH2–CH3 CH3
PART-B (CARBONYL COMPOUND) ¼dkcksZfuy ;kSfxd½

19. Product of given reaction is
H2 / Pd(CaCO3 ) Quinoline
CH 3 –CH2–C– Cl  
O
(A) CH3–CH2 –CH2–OH (B*) CH 3 –C H2–C– H
O
(C) (D) None of these
ABC–3 - 4
ABC-2, 3 & 4
nh x;h vfHkfØ;k dk mRikn gS &

CH 3 –CH2–C– Cl 
H2 / Pd (CaCO3 , Dohuksyhu )
      
O
(A) CH3–CH2 –CH2–OH (B*) CH 3 –C H2–C– H
O
(C) (D) buesa ls dksbZ ugha
20. Predict the reactant

O
H2 / Pd (BaSO 4 )
Reactant      CH3–CH2–C–H
fØ;kdkjd dks igpkfu,
O
H2 / Pd (BaSO 4 )
fØ;kdkjd      CH3–CH2–C–H
O
(A) CH3–CH2–CH2OH (B*) CH3–CH2–C–Cl
O
(C) CH3–CH2–CH2–Cl (D) CH3–C–Cl
H2
21. X   Y
Pd(BaSO 4 )
X is :
H2
X   Y
Pd(BaSO 4 )
VkWysu
vfHkdeZd
X gS :
(A) (B)
(C*) (D)
PCC
22. CH3–CH–CH2–OH  X
CH3
O
(A) CH3–CH–COOH (B) CH3–C
CH3 CH2–CH3
(C*) CH3–CH–CHO (D) CH3–C=O
CH3 CH3
ABC–3 - 5
ABC-2, 3 & 4
23. Which of the following is product of given reaction

HO OH
PCC
(Pyridinium
Chlorochromate)
CH2OH
nh x;h vfHkfØ;k dk mRikn gS &
HO OH
PCC
¼fijhMhuh;e Dyksjks ØksesV½
CH2OH
O O O O
(A*) (B)
CHO COOH
O O
HO OH
(C) (D) None of these buesa ls dksbZ ugha
COOH
24.
X is :
VkWysu
vfHkdeZd
X gS :
(A) (B) (C*) (D)
(i ) SnCl2 / HCl
25. CH3–CN    X + NH4Cl
(ii ) H2O
Identify ‘X’ : ‘X’ igpkfu,
(A*) CH3–CH=O (B) CH3–CH2–CH=O (C) CH3CH2OH (D) CH3CH(OH)CH3
ABC–3 - 6
ABC-2, 3 & 4
O
C–H
(i ) SnCl2 / HCl
26. R   
(ii ) H2O
Identify ‘R’ : ‘R’ igpkfu,
CN CH2–OH NH2 CH3

(A*) (B) (C) (D)
O
Ph–C–O Dry distillation
27.  Product
Ca    
Ph–C–O
O
O
Ph–C–O ' kq" d vklou
Ca    
 mRikn
Ph–C–O
O
O O O OH
(A) Ph–C–H (B*) Ph–C–Ph (C) Ph–C–C–Ph (D) Ph–C–C–Ph
O O H
O
Ph–C–O Dry distillation
28.  Product
Ca    
H–C–O
O
O
Ph–C–O ' kq" d vklou
Ca    
 mRikn
H–C–O
O
O O
(A*) Ph–C–H (B) Ph–C–Ph (C) H–C–H (D) Ph–C–C–H
O O O

29. Ca-Salt of Carboxylic acid 
X and Y
(A*) (H–COO)2Ca + (CH3–COO)2 Ca (B) (HCOO)2Ca + (CH3–CH2–COO)2Ca
(C) (CH3COO)2Ca + (CH3CH2–COO)2Ca (D) None of these

dkcksZfDlfyd vEy ds dSfY'k;e yo.k 
X rFkk Y gS &
(A*) (H–COO)2Ca + (CH3–COO)2 Ca (B) (HCOO)2Ca + (CH3–CH2–COO)2Ca
(C) (CH3COO)2Ca + (CH3CH2–COO)2Ca (D) buesa ls dksbZ ugha
ABC–3 - 7
ABC-2, 3 & 4
Chemical properties
jklk;fud xq.k
30. Benzaldehyde, when heated with conc. KOH solution, gives
(A) C6H5CH2OH only (B) C6H5COOH only
(C) C6H5COOK only (D*) a mixture of C6H5COOK and C6H5CH2OH
cSUtfYMgkbM dks lkUnz KOH foy;u ds lkFk xeZ djus ij curk gS &
(A) dsoy C6H5CH2OH (B) dsoy C6H5COOH
(C) dsoy C6H5COOK (D*) C6H5COOK rFkk C6H5CH2OH dk feJ.k
31. The Cannizzaro’s reaction is not given by :

dSuhtkjks vfHkfØ;k ugh nsrk gS &
(A) C6H5CHO (B) HCHO (C*) CH3CHO (D) (CH3)3C–CHO
NaOH
32. In the reaction, (CH3)3CCHO + HCHO  
 A + B
heat
the products (A) and (B) are respectively :
(A*) (CH3)3CCH2OH and HCOO– Na+. (B) (CH3)3CCOONa and CH3OH.
(C) (CH3)3CCH2OH and CH3OH. (D) (CH3)3COONa and HCOO– Na+.
NaOH
(CH3)3CCHO + HCHO   A+B
xeZ
vfHkfØ;k esa mRikn (A) rFkk (B) Øe'k% gS &
(A*) (CH3)3CCH2OH ,oa HCOO– Na+. (B) (CH3)3CCOONa ,oa CH3OH.
(C) (CH3)3CCH2OH ,oa CH3OH. (D) (CH3)3COONa ,oa HCOO– Na+
SnCl HO
33. ( X )  

HCl
2
  C6H5COO  C6H5CH2 – OH
(A) (B) (C) (D*) C6H5–CN
34. Which of the products is formed when acetone is reacted with dil. NaOH solution after heating?
tc ,lhVksu dks ruq NaOH foy;u ds lkFk xeZ fd;k tkrk gS rks cuus okyk mRikn gksxk \
O CH3 O
||
(A*) CH3–C–CH=C–CH3 (B) CH3 – C – CH – CH – CH3
| |
CH3 OH
O OH OH
| |
(C) CH3–C–CH2–C=CH2 (D) CH3 – C — C – CH3
| |
CH3 CH3 CH3
35. Product is : mRikn gSA
(A) (B*) (C) (D)
ABC–3 - 8
ABC-2, 3 & 4
(i ) dil. NaOH
36. Reactant    CH3–CH=CH–C–H
(ii ) 
O
Reactant is :
(i ) dil. NaOH
fØ;kdkjd    CH3–CH=CH–C–H
(ii ) 
O
fØ;kdkjd gSA
O O O O
(A) CH3–CH3 (B) H–C–C–H (C) CH3–C–CH3 (D*) CH3–C–H

37.
(A) H–CN (B*) CH3–CN (C) CH3–CH2–CN (D) CH3–COCl
38. The reaction,

(i ) CH3COONa / 453K
C6H5CHO + (CH3CO)2O      C6H5CH = CHCOOH
(ii ) H / H2O
is called
(A) Benzoin condensation (B) Aldol condensation
(C) Etard reaction (D*) Perkin's reaction
(i ) CH3COONa / 453K
C6H5CHO + (CH3CO)2O      C6H5CH = CHCOOH
(ii ) H / H2O
vfHkfØ;k dgykrh gS
(A) csUtgksbu la?kuu (B) ,YMkWy la?kuu
(C) bZVkMZ vfHkfØ;k (D*) ifdZu vfHkfØ;k
39. Predict the reactant for the given reaction.

CH3
CH=C–COOH
(CH CH CO) O
Reactant 
3 2 2


CH3 CH2COONa, 
(A) Benzene (B) (CH3CH2CO)2O (C) CH3COOH (D*) Benzaldehyde

nh x;h vfHkfØ;k esa fØ;kdkjd gS &
CH3
CH=C–COOH
(CH3 CH2CO)2 O
fØ;kkdkjd  
CH3 CH2COONa,

(A) csUthu (B) (CH3CH2CO)2O (C) CH3COOH (D*) csUtsfYMgkbM
40. Product mRikn

O O O
(A) C6H5CH=CH–C–O–C–CH3 (B*) C6H5–CH=CH–C–OH
O
OH O O H CH2–C
(C) C6H5–CH–CH2–C–O–C–CH3 (D) C6H5–C O
CH2–C
O
ABC–3 - 9
ABC-2, 3 & 4
H2 ,Pd,BaSO4 (CH CO) O

41. (X)  3 2
   C6H5–CH=CH–COOH

CH3 COONa,
(A) (B) (C) (D*)
42. The structure of the compound when acetaldehyde reacts with oxime is
,lhVSfYMgkbM dh vkWfDle ds lkFk vfHkfØ;k djkus ij izkIr mRikn gksxk &
(A) CH3CH = NCONHNH2 (B) CH3CH = NNHCONH2
(C*) CH3CH = NOH (D) CH3CH = NNH2
CH3 OH
43. 
(X) + (Y)  C=N
– H2O H
idenitfy (X) and (Y)
(X) rFkk (Y) igpkfu, &
CH3 CH3
(A) X  C=O ; y = NH2CONHNH2 (B) X  C=O ; y = NH2–NH2
H H
CH CH3
(C*) X  3 C=O ; y = NH2–OH (D) X  C=O ; y = NH2–NH–Ph
H H
44.
H2
Identify (X) and (Y).
(X) rFkk (Y) igpkfu, &
(A*) (B)
(C) (D)
45. Benzaldehyde and acetone can be distinguished by

(A) Mulliken Baker test (B) Fehling solution
(C*) Iodoform test (D) Ninhydrin test
csUtsfYMgkbM rFkk ,flVksu dks foHksfnr dj ldrs gSA
(A) eqfydu csdj ijh{k.k }kjk (B) Qsgfyax foy;u
(C*) vk;ksMksQkeZ ijh{k.k }kjk (D) uhugkbfMªu ijh{k.k }kjk
46. Acetaldehyde and benzaldehyde can be distinguished by
(A) Tollen's test (B*) Fehling solution
(C) FeCl3 test (D) NaHCO3 test
,flVsfYMgkbM rFkk csUtsfYMgkbM dks foHksfnr dj ldrs gSA
(A) VkWysu ijh{k.k }kjk (B*) Qsgfyax foy;u
(C) FeCl3 ijh{k.k }kjk (D) NaHCO3 ijh{k.k }kjk
47. Propanal and propanone can not be distinguished by

(A) Iodoform test (B) Fehling solution
(C) Tollen's test (D*) 2,4- DNP test
izksisusy rFkk izksisukWu dks foHksfnr ugha dj ldrs gSA
(A) vk;ksMksQkeZ ijh{k.k }kjk (B) Qsgfyax foy;u
(C) VkWysu ijh{k.k }kjk (D) 2,4- DNP ijh{k.k }kjk
ABC–3 - 10
ABC-2, 3 & 4
48. Which of the following compound will not react with I2/OH–.
fuEu esa ls dkSulk ;kSfxd I2/OH– ds lkFk vfHkfØ;k ugh djrk gSaA
(A) (B) (C*) (D) CH3 – CHO
Sol. group gives positive iodoform test.
gy % lewg /kukRed vkW;ksMksQkWeZ ijh{k.k nsrk gSA
49. 2-Pentanone can be distinguished from 3- Pentanone by which reagent ?

(A) 2, 4- Dinitrophenyl hydrazine (B) Tollen's reagent
(C*) I2 and dilute NaOH (D) Fehling solution
2-isUVsukWu vkSj 3- isUVsukWu dks fuEu esa ls fdl vfHkdeZd }kjk foHksfnr fd;k tk ldrk gSA
(A) 2, 4-MkbukbVªks QSfuy gkbMªsthu (B) VkWysu vfHkdeZd
(C*) I2 vkSj ruq NaOH (D) Qsgfyax foy;u
Sol. Iodoform test. (vk;ksMksQkeZ ijh{k.k)
50. Tollen’s reagent (AgNO3 + NH4OH) can be used to distinguish between.
(A) and (B) and
(C*) and (D) and
VkW y s u vfHkdeZ d (AgNO3 + NH4OH) ls fuEu es a foHks n dj ldrs gS A
(A) rFkk (B) rFkk
(C*) rFkk (D) rFkk
Sol. Aldehydes gives black or silver mirror ppt. with tollen's reagent.
gy % ,fYMgkbM VkWysu vfHkdeZd ds lkFk dkyk ;k jtr niZ.k vo{ksi nsrk gSA
ABC–3 - 11
ABC-2, 3 & 4
(A) ALKYL HALIDE

Preparation of Alkyl Halides (5-Methods)
1. From alcohol
SOCl2
(i) from (SOCl2) in presence of pyridine CH3–CH2–OH 
CH3–CH2–Cl + SO2 + HCl
Ethanol Pyridine Chloroethane
SOCl
R–OH 
2
 R–Cl+SO2+HCl
heat,pyridine
(ii) from PCl5 CH3–CH–OH+ PCl5 CH3–CH–Cl + HCl + POCl3

R–OH + PCl5 R–Cl + HCl + POCl3 CH3 CH3
Propan-2-ol 2-Chloropropane
(iii) from PX3

(PX PCl ,PBr ,PI )
3 3 3
3R–OH+PX3 3
 3R–X+H3PO3 3CH3–CH2–OH +PCl3 3CH3–CH2–Cl + H3PO3
Ethanol Chloroethane
(iv) from HX(X= Cl, Br,I)

ZnCl2 OH Cl
R–OH + HX R–X + H2O ZnCl2
+ HCl + H2 O
Cyclohexanol 1-Chlorocyclohexane
h
2. Halogenation of Alkane CH4 + Cl2 CH3Cl + HCl
Methane Chloromethane
Halogenation take place either at high
Cl
temperature (573 - 773 K) or in the presence
h
+ Cl2 + HCl
of diffuse sunlight or ultraviolet light.
Rate of reaction of alkanes with halogens : Cyclohexane 1-Chlorocyclohexane
F2 > Cl2 > Br2 > I2.

3. Addition of Hydrogen Halides CH2 CH2 + HBr CH3CH2Br
Ethene Bromoethane
Hydrogen halides add up to alkenes to form
Cl
alkyl halides. The order of reactivity of
CH3–C=CH2 + HCl CH3–C–CH3
hydrogen halides is HI > HBr > HCl.
CH3 CH3
2-Methylprop-1-ene 2-Chloro-2-methylpropane
4. Finkelstein reaction H H
Dry aceteone
Alkyl iodides often prepared by the reaction CH3 C CH3 + NaI CH3 C CH3 + NaCl
of alkyl chloride / bromide with Nal in dry Cl I
2-Chloropropane 2-Iodopropane
acetone. This reaction is known as
Br I
Finkelstein reaction. dry acetone
+ NaI + NaCI
1-Bromocyclohexane 1-Iodocyclohexane
ABC-2, 3 & 4 - 31
ABC-2, 3 & 4
5. Swart Reaction CH3 Cl + AgF CH3 F + AgCl

Chloromethane Fluoromethane
The synthesis of alkyl fluoride is best
Cl
accomplised by heating an alkyl chloride /
CH3 CH2 CH CH3 + AgF
bromide in the presence of a metallic fluoride
2-Chlorobutane
such as AgF, Hg2F2, CoF2 or SbF3.
CH3 CH2 CH CH3 + AgCl
The reaction is termed as Swart reaction. 2-Fluorobutane
F
Chemical Reactions of Alkyl Halide (4-Reactions)

1. Reaction of alkyl halide with H
(a) KCN CH3 CH CH3 + KCN CH3 C CH3 + KCl

KCN predominantly ionic and provides Cl CN
2-Chloropropane 2-Methylpropanenitrile
cyanide ions in solution. Although both
Br CN
carbon and nitrogen atoms are in a position + KCN + KBr
to donate electron pairs, the attack takes
1-Bromocyclohexane Cyclohexanecarbonitrile
place mainly through carbon atom and not
through nitrogen atom since C – C bond is
more stable than C – N bond.
(b) AgCN CH3 Cl + AgCN CH3NC + AgCl
Methylchloride Methylisocyanide
AgCN is mainly covalent in nature and
H
nitrogen is free to donate electron pair
CH3 CH CH3 + AgCN CH3 C CH3 + AgCl
forming isocyanide as the main product.
Cl NC
2-Chloropropane
(c) KNO2 H
Alkyl halides (R–X) react with KNO2 to give CH3 CH CH3 + KNO2 CH3 C CH3 + KCl
R–O–N=O (Alkylnitrite). Cl O–N=O
Iso-propylchloride Iso-Propylnitrite
Br O N O
+ KNO2 + KBr
Cyclohexylbromide Cyclohexylnitrite
(d) AgNO2 CH3 Cl + AgNO2 CH3NO2 + AgCl

Chloromethane Nitromethane
Alkyl halides (R–X) react with AgNO2 to
give R–NO2 (Nitroalkane) CH3 CH2 CH2 CH2 Cl+AgNO2
1-Clorobutane
CH3 CH2 CH2 CH2 NO2 + AgCl

1-Nitrobutane
ABC-2, 3 & 4 - 32
ABC-2, 3 & 4
(e) Aqueous KOH CH3 CH2 Cl + aq. KOH CH3 CH2 OH + KCl
Chloro ethane Ethanol
Alkyl halides (R–X) when reacts with
H H
aq. KOH gives alcohol
CH3 C CH3 + KOH(aq.) CH3 C CH3 + KCl
Cl OH
2-Chloropropane Propan-2-ol
dry ether
2. Wurtz Reaction CH3 Br + 2Na + Br CH3 CH3 CH3 + 2NaBr
Bromomethane Ethane
Alkyl halide on treatment with sodium
CH3 CH3
metal in dry ether solution give higher
CH3 C Br + 2Na + Br C CH3
alkanes. The reaction is known as
H H
Wurtz reaction. It is used for the 2-Bromopropane
preparation of higher alkanes CH3 CH3

dry ether
containing even number of carbon CH3 C C CH3 + 2NaBr
atoms. H H
2,2-Dimethyl butane
3. Wurtz-Fittig Reaction Br CH3

dry ether
+ 2Na + Br CH3 + 2NaBr
A mixture of an alkyl halide and aryl
Bromobenzene Methylbenzene
halide give an alkyl arene when treated Br
Br
with sodium in dry ether.
dry ether
+ 2Na + + 2NaBr
Bromobenzene Bromocyclohexane Cyclohexylbenzene
– +
4. Williamson Ether Synthesis CH3Cl + CH3O K CH3 – O – CH3 + KCl
Methyl Potassium Dimethyl
chloride methoxide ether
(B) ALCOHOL AND ETHERS

Preparation of Alcohols (4-Methods)
+
H 3O
1. From Grignard Reagents [R–Mg–X] (a) CH3MgBr + HCHO
Ether
CH3–CH2–OH
Grignard Reagent is an organometallic
+
compound. Grignard Reagent acts as base Ether H3O
(b) PhMgBr + CH3–CHO CH3–CH–OH
and nucleophile.
(i) HCHO Ph
R–CH2–OH (1° alcohol)
(ii) H3O
CH3
(i) R–CHO Ether H3O
+
R–MgX R–CH–R (2° alcohol) (c) CH3–CH2MgBr + CH3–C–CH3 CH3–C–OH
(ii) H3O
OH O CH2CH3
O R
(i) R–C–R
(ii) H3O R–C–R (3° alcohol)
OH
ABC-2, 3 & 4 - 33
ABC-2, 3 & 4
2. Syn hydroxylation of alkenes (a) H2C = CH2 

4 (i) OsO
H2CCH2
(ii) NaHSO3
Reagents : a. Baeyer's reagent: [cold OH OH
dilute 1% alkaline KMnO4] or 1% alk. KMnO4
(b) CH3–CH=CH2 CH3–CH–CH2
b. (i) OsO4 (ii) NaHSO3
OH OH
Baeyer's reagent OH
(i ) OsO
or (i)OsO4 (ii) NaHSO3 (c) 4
   
(ii ) NaHSO 3
OH OH OH
Remark
It is syn addition. Both OH groups add on
the same side of pi-bond.
3. Anti hydroxylation of alkene OH
Reagent: (a) +
H3 O
(i) Peroxyacid (RCOOOH) OH
+
(ii) H2O/H OH
PAA
(b) CH3–CH=CH–CH3 H O+ CH3–CH–CH–CH3
Peroxyacid 3
OH
OH
OH ( i) Peroxy acid
    

H 3 O
C–C (c) (ii) H3O 
OH
OH
Remark
It is anti addition. Both OH groups add on
the opposite side of pi-bond.
Peroxyacid may be any one of these:
a. m-CPBA (Metachloro perbenzoic acid)
b. PAA (Peracetic acid)
c. PBA (Per benzoic acid)
d. TFPAA (Trifluoro peracetic acid).
4. Hydration of alkene (a)
(a) Acid Catalysed hydration :
+ +
Reagents: dil. H2SO4 or H2O/H or H3O H2O/H
| | (b) CH3–CH=CH–CH3 CH3–CH–CH–CH3
H2O/H – C – C –
H OH
| |
H OH
Remarks: Markovnikov's addition
ABC-2, 3 & 4 - 34
ABC-2, 3 & 4
(b) Hydroboration-oxidation reaction: (a)

(i) B2H6.THF
CH3–CH2–CH=CH2 CH3–CH2–CH–CH2
(ii) H2O2 OH
Butene
Reagents : (i) BH3, or B2 H6 /THF H OH
(ii) H2O2/ OH CH3 CH3

(b) (i) B2H6.THF
H
(ii) H2O2 OH
(i) B2H6.THF
| | OH
–C–C–
(ii) H2O2 OH | |
H OH
Remarks: Anti Markovnikov's addition ; Syn

addition of H and OH.
Preparation of Ethers (2-Methods)

1. Williamson synthesis
(a) CH3–X + CH3–CH2–CH2O–Na CH3–O–CH2CH2CH3
It is an important laboratory method for
the preparation of symmetrical and
unsymmetrical ethers. In this method, an (b) CH3CH2–X + PhO–Na Ph–O–CH2–CH3
alkyl halide is allowed to react with sodium

alkoxide. (c) Ph–CH2–X +Ph–CH2–O–Na PhCH2–O–CH2–Ph
– +
RX + RO–Na R–O–R + NaX
H2SO4
2. From alcohol (a) CH3–CH2–OH 413 K
C2H5–O–C2H5
Alcohols undergo dehydration in the
presence of protic acids (H2SO4, H3PO4) H2SO4
(b) CH3–OH + CH3OH CH3–O–CH3
413 K
at 413K temperature.
H SO H2SO4
R–OH 
2 4
 R–O–R (c) CH3–OH + CH3–CH2–OH 413 K CH3–O–CH3
413 K
Remark :
Alcohols undergo dehydration by heating
+ CH3–CH2–O–CH2–CH3 + CH3–O–CH2–CH3
with conc. H2SO4 at 443K and give
alkene.
Chemical Reactions of Alcohols (5-Reactions)

1. Reaction with HX:
HBr
R–OH + HX R–X + H2O (a) CH3–CH2–OH CH3–CH2–Br
The reactions of primary and secondary

alcohols with HCl require a catalyst
HCl
(ZnCl2). With tertiary alcohols, the reaction (b) CH3–CH–OH ZnCl2
CH3–CH–Cl
conduct by simply shaking with CH3 CH3
concentrated HCl at room temperature.
ABC-2, 3 & 4 - 35
ABC-2, 3 & 4
2.
Reaction with phosphorus (a) CH3–CH2–CH2–OH PBr3
CH3–CH2–CH2–Br
trihalides:
CH3
3R – OH + PX3 3R – X + H3PO3 | PCl3
(b) CH3 – CH2 – CH – CH2 – OH  
PX3 = PCl3, PBr3, PI3
CH3
|
CH3 – CH2 – CH – CH2 – Cl
3. Reaction with PCl5

S N2 (a) PhCH2 OH PCl5 PhCH2Cl + POCl3
R–OH + PCl5 R–Cl + HCl + POCl3
PBr5
(b) CH3 CH OH CH3 CH Br
CH3 CH3
SOCl2
4. Reaction with thionyl chloride in (a) CH3–CH2–OH pyridine
CH3–CH2–Cl
presence of pyridine:
SOBr2
pyridine (b) Ph–CH2–OH pyridine Ph–CH2–Br
R – OH + SOCl2 R – Cl + SO2 + HCl
Conc. H2SO4
5. Reaction with conc. H2SO4 /  (a) CH3 CH CH3 
CH3 CH CH2
OH
Conc. H2SO4

CH3 CH3
(b) CH3 Conc. H2SO4
CH3–CH=CH–CH3 C CH3 CH3 C CH2

Remarks : OH
i. Ease of dehydration of alcohol CH3 CH3

Conc. H2SO4
    3o > 2o > 1o (c) CH3 CH2 C CH3 CH3 CH C CH3

ii. More stable alkene (Saytzeff Alkene) OH

is formed as major product
Chemical Reactions of Ethers (1-Reaction)

H2O/H
1. Hydrolysis of Ethers (a) CH3–O–CH3 2CH3–OH
Ether is hydrolysed in acidic medium and H 3O+
(b) CH3–CH2–O–CH2–CH3 2CH3–CH2–OH
produce two alcohols. Dil. H2SO4
+ + (c) Ph–CH2–O–CH2–CH3
Reagent : dil H2SO4 or H3O or H2O/H
Ph–CH2–OH + CH3–CH2–OH
H2O/H
R–O–R R–OH + R–OH
ABC-2, 3 & 4 - 36
ABC-2, 3 & 4
Test of Alcohols (3-Test)

S.No Test / Reagent Observation
1 Cerric ammonium nitrate test Red colour compounds is formed
Reagent : [(NH4)2Ce(NO3)6]
2 Lucas Reagent (a) 1° alcohol does not give appreciable reaction or white
Reagent : [Conc. HCl + anhyd. ZnCl2] turbidity in 30 minute.

(b) 2° alcohol gives white turbidity in 5 minute.
Remarks : It gives white turbidity or
(c) 3° alcohol gives white turbidity immediately.
cloudiness with alcohols (OH groups
attached with sp3 hybridised carbon).
3 Victor Mayer test (a) 1° alcohol – Blood red colour.
Reagent : (i) P + I2 (b) 2° alcohol – Blue colour.

(c) 3° alcohol – No colour.
(ii) AgNO2
(iii) HNO2
(iv) Base
ABC-2, 3 & 4 - 37
ABC-2, 3 & 4

PART-A (ALKYL HALIDES) ¼,fYdy gSykbM½
CH2–OH
1. + PCl3 [X] + H3PO3
Product [X] is : mRikn [X] gS -

CH3–OH
CH3
CH2–Cl CH3
Cl
(A*) (B) (C) (D)
Cl Cl
CH3
2. CH3–C–OH + HBr [Y] + H2O
CH3
Product [Y] is : mRikn [Y] gS -
CH3 CH3 CH3
(A*) CH3–C–Br (B) CH3–C–H (C) CH3–CH2–CH2–Br (D) CH3–C–CH2–Br
CH3 CH2–Br CH3
3. [X] + PCl5 CH3–CH2–CH2–Cl + HCl + POCl3

Reactant [X] is - vfHkdkjd [X] gS&
CH3
(A) CH3–CH–OH (B*) CH3–CH2–CH2–OH
CH3
(C) CH3–CH2–CH3 (D) CH3–CH–CH3
CH2–OH
4. + PCl5 [X] + HCl + POCl3
CH2–Cl CH2–Br
(A*) (B)
CH3 CH2–OH
Cl
(C) (D)
Cl
ABC–4 - 1
ABC-2, 3 & 4
CH3
5. h
CH3–C–CH3 + Cl2 [X] + HCl
CH3
Product [X] is - mRikn [X] gS -
CH3 CH3
(A) CH3–C–CH3 (B*) CH3–C–CH2 –Cl
Cl CH3
CH3 C 2H 5
(C) CH3–CH–CH2–Cl (D) CH3–C–Cl
C 2H 5
2 Cl / h
6. Iso-butane  
No of monochloro structural isomeric product
Cl / h
2
vkblks-C;wVsu  
eksuksDyksjks lajpukRed leko;oh mRikn dh la[;k gS&
(A) 1 (B*) 2 (C) 3 (4) 4
Cl / h
7. Iso octane 
2

Cl2 / h
vkblksvkWDVsu  
(A) 1 (B) 2 (C) 3 (D*) 4
Cl / h
8. Cyclopentane 2

Cl2 / h
DyksjksisUVsu  
(A*) 1 (B) 2 (C) 3 (D) 4
9. CH3–CH=CH2 + HBr  [Y]

Major product [Y] is : eq[; mRikn [Y] gS&
CH3
(A) CH3 CH CH2 Br (B) CH3 CH2 CH2 Br

Br
H
(C*) CH3 C CH3 (D) CH3 CH2 CH3

Br
Cl
10. [Z] + HCl
Reactant [Z] is : vfHkdkjd [Z] gS&

CH3
(A) (B) (C*) (D)
ABC–4 - 2
ABC-2, 3 & 4
Dry acetone
11. CH3–CH2–Cl + NaI [X] + NaCl
Product [X] is -
(A) CH3–CH3 (B*) CH3–CH2–I
(C) CH3–I (D) CH3–CH2–CH2–CH3
'kq"d ,lhVksu
CH3–CH2–Cl + NaI D [X] + NaCl
mRikn [X] gS -
(A) CH3–CH3 (B*) CH3–CH2–I
(C) CH3–I (D) CH3–CH2–CH2–CH3
CH2–I
12. [Z] + NaI Dry acetone
Reactant Z is :
CH2–Cl CH3 CH3 CH3
Cl
(A*) (B) (C) (D)
Br
Cl
CH2–I
'kq"d ,lhVksu
[Z] + NaI D
vfHkdkjd [Z] gS&

CH2–Cl CH3 CH3 CH3
Cl
(A*) (B) (C) (D)
Br
Cl
13. CH3–CH2–Cl + AgF X] + AgCl
Product [X] is - mRikn [X] gS -
(A) CH3–CH3 (B*) CH3–CH3–F (C) CH3–CHF2 (D) CH3–F
CH2–Cl CH2–F
14. + [Y] 
Reagent [Y] can be : vfHkdeZd [Y] gS -

(A) AgF (B) Hg2F2 (C) SbF3 (D*) All
15. [Z] + SbF3 F

Reactant [Z] is : vfHkdkjd [Z] gS&
(A) (B) (C*) Cl (D)
16. CH3–CH2–CH2–Cl + KNO2 [X] + KCl

(A*) CH3–CH2–CH2–O–N=O (B) CH3–CH2–CH2–NO2
(C) CH3–CH2–CH3 (D) CH3–CH=CH2
17. CH3–CH2–CH2–Cl + Cl + AgNO2 [X] + AgCl

(A) CH3–CH2–CH2–O–N=O (B*) CH3–CH2–CH2–NO2
(C) CH3–CH2–CH3 (D) CH3–CH=CH2
ABC–4 - 3
ABC-2, 3 & 4
CH3
+
18. CH3–C–O–K + CH3–Br [Y] + KBr
CH3
Product [Y] is : mRikn [Y] gS -
CH3
(A) CH2 (B) CH3 (C*) CH3–C–O–CH3 (D) CH3–CH3
CH3–C–CH3 CH3–C–CH2–CH3 CH3
CH2–Br
19. + KOH (aq.) [X] + KCl

CH3
CH2–OH CH3 CH2–Cl
(A*) (B) (C) (D)
OH OH
CH3 CH3
20. In wurtz reaction, CH3–CH–CH–CH3 can be prepared from which of the following compound?
CH3 CH3
oqVZ~t vfHkfØ;k esa CH3–CH–CH–CH3 fuEu esa ls dkSuls ;kSfxd ls fufeZr gks ldrk gS \
CH3 CH3
(A*) CH3–C–Br (B) CH3–CH2–CH2–Br (C) CH3–CH2–Br (D) CH3–C–CH2Br
H CH3
21. [X] + Na Dry ether
Reactant [X] is -
Br Br
(A) (B) (C*) (D)
[X] + Na 'kq"d bZFkj
vfHkdkjd [X] gS&

Br Br
(A) (B) (C*) (D)
Br
22. + C2H5Br + 2Na Dry ether [X] + 2NaBr
Major product [X] is -

C2H5
CH3
(A) (B*) (C)CH3–CH2–CH2–CH3 (D) None of these
ABC–4 - 4
ABC-2, 3 & 4
Br
+ C2H5Br + 2Na 'kq"d bZFkj [X] + 2NaBr
eq[; mRikn [X] gS&

C2H5
CH3
(A) (B*) (C)CH3–CH2–CH2–CH3 (D) buesa ls dksbZ ugha
PART-B (Alcohol & Ethers) ¼,YdksgkWy ,oa bZFkj½

23. Which carbonyl compound is used for following interconversion:
fuEu vUrj ifjorZu ds fy, dkSulk dkcksZfuy ;kSfxd iz;qDr gksrk gS–
CH3
H3 O
Carbonyl compound + CH3–CH2–MgBr + X  CH3–CH2–C–CH3
OH
(A) CH3–CHO (B) HCHO (C*) CH3–C–CH3 (D) CH3–CH2–CHO
O
24. Which is correct product for given reaction? nh xbZ vfHkfØ;k ds fy, lgh mRikn dkSulk gS ?
H O
CH3–CH2–CHO + PhMgBr 
3
P
CH3 CH3
(A*) CH3–CH2–CH–OH (B) CH3–C–OH (C) CH3–CH–CH2–OH (D) Ph–CH2–CH2–CH2–OH
Ph Ph Ph
25. Which of the following carbonyl compound will give 1° alcohol after reaction with Grignard reagent
followed by acidification:
fuEu esa ls dkSulk dkcksZfuy ;kSfxd fxU;kj vfHkdeZd ds lkFk vfHkfØ;k ds i'pkr~ vEyh; dj.k ij 1° ,YdksgkWy
nsrk gS %
(A*) HCHO (B) CH3–CHO (C) CH3–CH2–CHO (D) CH3–C–CH2–CH3
O
26. For the following reaction:
OsO / NaHSO
4 3
  P.
Product is:
OH OH OH
(A) (B*) (C) (D) OH
OH OH
ABC–4 - 5
ABC-2, 3 & 4
fuEu vfHkfØ;k ds fy,:
OsO / NaHSO
4 3
  P.
mRikn gS&
OH OH OH
(A) (B*) (C) (D) OH
OH OH
27. For the following reaction :
CH3–CH=CH–CH3  CH3–CH–CH–CH3

OH OH
Reagent is:
(A) HCl (B) Dil. H2SO4 (C*) Bayer's reagent (D) H2/Ni
fuEu vfHkfØ;k ds fy, :
CH3–CH=CH–CH3  CH3–CH–CH–CH3

OH OH
vfHkdeZd gS :
(A) HCl (B) Dil. H2SO4 (C*) cs;j vfHkdeZd (D) H2/Ni
28.
Reagent x will be :
(A) 1% alkaline KMnO4 (Baeyer’s reagent) (B) OsO4 /NaHSO3
(C) Peracid/H3O+ (D*) A and B both
vfHkdeZd x gksxk&
(A) 1% {kkjh; KMnO4 (cs;j vfHkdeZd) (B) OsO4 /NaHSO3
(C) ijvEy/H3O+ (D*) A o B nksuksa
ABC–4 - 6
ABC-2, 3 & 4
(i)peroxy acid
29. CH3–CH=CH–CH3 

P
(ii)H3O
Product is:
(i) ijksDl h vEy
CH3–CH=CH–CH3 
(ii) H3O
mRikn gS&
OH
(A) CH3–CH2–CH–CH2 (B*) CH3–CH–CH–CH3
OH OH OH
OH
(C) CH3–CH2–CH2–CH (D) CH2–CH2–CH2–CH2
OH
OH OH
CH COOOH / H O
30. 3 3
  Product

Product will be:

CH3 CH3 OH
OH CH3
(A) OH (B*) (C) (D) None of these
H OH OH
OH H H
3CH COOH / H O
3
 mRikn
mRikn gksxk&
CH3 CH3 OH
OH CH3
(A) OH (B*) (C) (D) dksbZ ugha
H OH OH
OH H H
(1) Peroxyacid
31.      P
( 2 ) H3O 
Product is :
(A) (B*) (C) (D) None of these
(1) ijkWDlh vEy

 
 P mRikn gS&
(2) H3 O
(A) (B*) (C) (D) buesa ls dksbZ ugha
ABC–4 - 7
ABC-2, 3 & 4
32. Predict the product of the following reaction:

fuEu vfHkfØ;k dk mRikn crkb;s&
H2 / Ni H O
CH2=CH–CH2–O–CH2–CH3  3
 
(A) CH2=CH–CH2–OH; CH3–CH2–OH (B*) CH3–CH2–CH2–OH ; CH3–CH2–OH
(C) CH3–CH2–CH3; CH3–CH2–OH (D) CH3–CH2–CHO; CH3–CH2–OH
33. Predict the product of the following reaction: fuEu vfHkfØ;k dk mRikn crkb;s&
2Dil. / H SO
4
 
O
OH
(A) HO (B*) HO OH
CHO OH
(C) OHC (D) HO
34. What is the final product of the following reaction :

fuEu vfHkfØ;k dk vfUre mRikn gS&
NaOH CH –Cl
Ph–OH  3
 
(A*) Ph–O–CH3 (B) Ph–CH3 (C) Ph–O–CH2–CH3 (D) Ph–Cl
35. In the following reaction:
C2H5ONa + C2H5Cl  product

Product is:
(A) C2H5–O–CH3 (B*) C2H5–O–C2H5 (C) CH3–O–CH3 (D) C2H5–C2H5
fuEu vfHkfØ;k esa
C2H5ONa + C2H5Cl  mRikn

mRikn gS&
(A) C2H5–O–CH3 (B*) C2H5–O–C2H5 (C) CH3–O–CH3 (D) C2H5–C2H5
36. Predict the suitable reagent for the following conversion:
CH3–CH2–OH  CH3–CH2–O–CH2–CH3

(A) dil. H2SO4 (B) conc. H2SO4 / 200°C
(C*) conc. H2SO4 / 140°C (D) Al2O3
fuEu :ikUrj.k ds fy, mi;qDr vfHkdeZd gS&
CH3–CH2–OH  CH3–CH2–O–CH2–CH3

(A) ruq H2SO4 (B) lkUnz H2SO4 / 200°C
(C*) lkUnz H2SO4 / 140°C (D) Al2O3
ABC–4 - 8
ABC-2, 3 & 4
37. In the following reaction:

Conc.H SO
CH3–OH + CH3–CH2–OH 
2 4
product:
100–140 C
Which is not a possible product:
(A) CH3–O–CH2–CH3 (B) CH3–O–CH3
(C*) CH3–O–CH2–CH2–CH3 (D) CH3–CH2–O–CH2–CH3
fuEu vfHkfØ;k esa:

CH3–OH + CH3–CH2–OH lkUnzH2SO4 mRikn :
100–140°C
dkSulk mRikn lEHko ugha gS&
(A*) CH3–O–CH2–CH3 (B) CH3–O–CH3
(C) CH3–O–CH2–CH2–CH3 (D) CH3–CH2–O–CH2–CH3
38. Predict the reagent for the following reaction:

Ph–CH2–OH  Ph–CH2–O–CH2–Ph
(A) dil. H2SO4 (B) KMnO4 (C) LiAlH4 (D*) conc. H2SO4 / 140°C
fuEu vfHkfØ;k ds fy, vfHkdeZd crkb;s&
Ph–CH2–OH  Ph–CH2–O–CH2–Ph
(A) ruq H2SO4 (B) KMnO4 (C) LiA/H4 (D*) lkUnz H2SO4 / 140°C
39. Which alcohol give instant turbidity with Lucas reagent:

dkSulk ,YdksgkWy Y;wdkl vfHkdeZd ds lkFk 'kh?kzrk ls xanykiu nsrk gS&
CH3
(A) CH3–CH2–OH (B) CH3–CH–CH3 (C*) CH3–C–CH3 (D) CH3–CH2–CH2–OH
OH OH
40. Which alcohol give white turbidity after 5 minute with Lucas reagent:–
dkSulk ,YdksgkWy Y;wdkl vfHkdeZd ds lkFk 5 feuV i'pkr~ 'osr xanykiu nsrk gS&
Ph CH3
(A) CH3–CH2–OH (B) Ph–C–CH3 (C*) CH3–CH–CH2–CH3 (D) CH3–C–CH3
OH OH OH
41. Which can distinguish 1°, 2° and 3° alcohol :

(A*) Victor Mayer test (B) Iodoform test (C) NaHCO3 test (D) Bayer's test
dkSulk ijh{k.k 1°, 2° o 3° ,YdksgkWy esa foHksnu dj ldrk gS :
(A) foDVj es;j ijh{k.k (B) vk;ksMksQkeZ ijh{k.k (C) NaHCO3 ijh{k.k (D) cs;j ijh{k.k
42. Which test is not used for Alcohol

(A) Lucas Test (B*) Neutral FeCl3 Test
(C) Victor major test (D) Cerric ammonium nitrate test
,YdksgkWy ds fy, dkSulk ijh{k.k iz;qDr ugha gksrk gS&
(A) Y;wdkl ijh{k.k (B*) mnklhu FeCl3 ijh{k.k
(C) foDVj es;j ijh{k.k (D) lsfld veksfu;e ukbVªsV ijh{k.k
ABC–4 - 9

Organic Phenol, Aniline, Carboxylic Acid

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Organic Phenol, Aniline, Carboxylic Acid

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ABC-2, 3 & 4

ABC-2 (Phenol & Aniline)

3. Fusion of Benzene sulphonic acid

phenol. Benzene sulphonic acid is melted Benzene Phenol

320°C) followed by hydrolysis which yields

4. Decarboxylation of salicylic acid OH OH

5. Hydrolysis of Benzene diazonium + –

Chemical Reactions of Phenol [5-Reactions]

(b) Reaction with Br2/CS2 OH

2. Reimer Tiemann formylation OH OH OH

3. Reimer Tiemann carboxylation OH OH OH

Note: Salicyclic acid can be used in formation of O

4. Kolbe's Schmidt Reaction OH O–

Lab test for Phenol

Preparation of Aniline [3-Methods]

R can be : Alkyl or phenyl

2. Chemical reactions of diazonium salt

1. Complete the following reactions.

H2/Pd Sandmayer reaction

Lab test of Aniline :

R–NH2 + CHCl3 + 3KOH Heat R–NC + 3KCl + 3H2O

2. Azo dye test

3. Bromine water Test (Br2 + H2O):

ONLY ONE OPTION CORRECT TYPE

(A*) Phenol (B) Aniline (C) Anisole (D) Benzene

2. Identify the product of following reaction.

fuEu vfHkfØ;k dk mRikn igpkfu;s&

(A*) (B) (C) (D) None of thesemijksä esa ls dksbZ ugh

3. Identify the product of the following reaction.

fuEu vfHkfØ;k dk mRikn igpkfu;s&

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SO3H SO3H OH CH3

5. Give the product for following reaction.

fuEu vfHkfØ;k dk mRikn igpkfu;s&

C2H5 C2H5 C 2H5

6. Identify the X and Y in the following reaction.

fuEu vfHkfØ;k esa X ,oa Y dks igpkfu;s&

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7. What will be the product of following reaction?

fuEu vfHkfØ;k dk mRikn D;k gksxk\

8. Find the product for the following reaction.

fuEu vfHkfØ;k dk mRikn D;k gksxk\

9. Give the major product for the following reaction.

fuEu vfHkfØ;k dk eq[; mRikn D;k gksxk\

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mijksä esa ls dksbZ ugh

fuEu vfHkfØ;k dk mRikn crkb;sA

mijksä esa ls dksbZ ugh

fuEu vfHkfØ;k esa vfHkdkjd gksxk\

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14. Sn/HCl R is gS&

NO2 NH2 NH2 NH2

(A) (B) (C*) (D)

NO2 NO2 NO2

(A) (B) (C*) (D)

NO2 NO2 NO2 NO2

(A) (B*) (C) (D)

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CH3 CH3 CH3 CH3

19. Which of them produces diazonium cation at 0°C ?

buesa ls fdlds }kjk 0°C ij MkbZ,stksfu;e /kuk;u dk fuekZ.k laHko gSS

(A) Cu2Cl2/HCl (B) Cu/HCl (C*) C2H5OH (D) HBF4

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