Alcohols, Phenols and Ethers

NARAYANA SR.
AIEEE MATERIAL 137 ALCOHOL
ALCOHOL
H 3C
SYNOPSIS:
NOMENCLATURE:
CH  CH 2OH
isobutyl alcohols etc. are
i). Alcohols contain the functional group -OH
(hydroxyl group)
H3C
ii) From a given alkane one, two, three hydrogen primary alcohols.
atoms may be replaced by one, two, three ii) Secondary alcohols contain -OH group bound to a
hydroxyl groups, to give monohydric, dihydric, Secondary carbon atom.
trihydric alcohols respectively Example:
iii) The general name polyhydric alcohol indicates
that the alcohols contains more than one -OH H 3C
group.
CH  OH
MONOHYDRIC ALCOHOLS: Isopropyl alcohol ,
Methyl alcohol  CH 3OH  , H3C
Ethyl alcohol  C2 H 5OH  , CH 3  H 2 C

sec. butyl alcohol C H  O H are
isopropyl alcohol  CH 3  CHOH,
2
H3C
Tertiary butyl alcohol  CH 3 3 COH etc.are iii). Tertiary alcohol contain-OH group bound to a
monohydric alcohols tertiary carbon atom.
Example:
 CH 2OH  CH 2 OH  is dihydric
POLYHYDRIC ALCOHOLS: CH 3
glycerol  CH 2OH  CHOH  CH 2OH  CH 3  C  OH
is trihydric, sorbitol or Tertiary butyl alcohol: ,
CH 3
mannitol CH OH  CHOH 
2 4
 CH 2OH  
is hexahydric. CH 3
MONOHYDRIC ALCOHOLS(R-OH):The general
formula of the homologous series of monohydroxy
CH 3  CH 2  C  OH
Tertiary amyl alcohol
alkanes is Cn H 2n1OH or R  OH
CH 3
where R is alkyl group.
i). If -OH group is bound to a primary carbon atom it
is called a primary alcohol.  COMPOUNDS CONTAINING Csp 3  OH : In
Ex: Methyl alcohol H  CH 2OH  ; this class of alcohols, the -OH group is
attached to an Sp 3 hybridised carbon atom of
ethyl alcohol  CH 3  CH 2  OH  ; an alkyl group. they are further classified as
follows:
n-Propyl alcohol
CH 3  CH 2  CH 2  OH  ; primary  H  CH 2OH 

NARAYANA SR.AIEEE MATERIAL 138 ALCOHOL
COMMON SYSTEM OF NOMENCLATURE:

H 3C In this system the names of alcohols are given by
CH  OH the radico functional system in which the alkyl
Secondary group that bears-OH is named first and the word
H3C alcohol is added next.
Example:
CH 3 Methyl alcohol  CH 3OH  ,

CH 3  C  OH Ethyl alcohol  C2 H 5OH  ,
Tertiary
CH 3 H 3C
CH  OH
 ALLYLIC ALCOHOLS: In these alcohols, the - Isopropyl alcohol
OH group is attached to a sp 3 hybridised carbon H3C
next to the carbon carbon double bond, that is
to an allylic carbon. CH 3
Primary CH 2  CH  CH 2  OH
CH 3  C  OH
H Tertiary butyl alcohol:
|
CH 2  CH  C|  OH CH 3
Secondary
C 
|
n-butyl alcohol CH 3CH 2CH 2CH 2OH
 BENZYLIC ALCOHOLS: In these alcohols, the
CH 3  CH 2  CH  CH 3
- OH group is attached to a sp 3 -hybridised
carbon atom next to an aromatic ring.
sec.butyl alcohol
|
OH
IUPAC SYSTEM:
i). The substitutive names of alcohols are given by
identifying the longest continuous carbon chain
allylic and benzylic alcohols may be primary, containing the hydroxyl group and replacing the
ending letter of the name of the corresponding
secondary or tertiary.
alkane ‘e’ by ‘ol’.
 COMPOUNDS CONTAINING Csp 3  OH bond: ii). The carbon atoms in the identified longest
chain are numbered such that the carbon
These alcohols contain -OH group bonded to a carrying the -OH group gets the lowest possible
carbon - carbon double bond i.e., to a vinylic number.
carbon or to an aryl carbon. These alcohols are
also known as vinylic alcohols. CH 2  CH  CH 2
 Propane -1, 2, 3 - triol | |
OH OH OH
|
Vinylic alcohol: CH 2  CH  OH
Compound Common Name IUPAC name

CH 3  OH Methyl alcohol Methanol
CH 3  CH 2  CH 2  OH n -Propyl alcohol Propan - 1 -ol
CH 3  CH  CH 3
| Isopropyl alcohol Propan - 2 -ol
OH
CH 3  CH 2  CH 2  CH 2  OH n  butyl alchol butan - 1 -ol
CH 3  CH  CH 2  CH 3
| sec -butyl alcohol Butan - 2 - ol
OH
CH 3
|
CH 3  C  CH 3
tert-Butyl alcohol 2-Methylpropan - 2 - ol
|
OH
CH 2  CH  CH 2
| | | Glycerol Propane -1, 2, 3 - triol
OH OH OH
i. FROM ETHYL HALIDE : Ethyl halide on hydrolysis
 Structure functional group In alcohols, the oxygen
with aqueous sodium hydroxide or potassium
of the -OH group is attached to carbon by a sigma hydroxide or silver oxide suspended in boiling
  bond f ormed by the ov erlap of a water forms ethyl alcohol.
sp 3 hybridised orbital of carbon with a CH 3 CH 2 X  NaOH ( aq )  CH 3 CH 2 OH  NaX
sp 3 hybridisecd orbital of oxygen. depicts Where X  Cl , Br , I

structuralaspects of methanol, phenol and
methoxymethane.
The bond angle in alcohols is slightly less than

CH 3CH 2 X  AgOH   CH 3 CH 2 OH  AgX
 0

the tetrahedral angle 109 28 ' . It is due to
the repulsion between the unshared electron pairs ii) FROM ETHYL ACETATE: Ethyl alcohol is formed
of oxygen. The C-O bond length (141 pm) is by the hydrolysis of ethyl acetate (an ester) with
almost the same as in alcohols. aqueous alkali.
MET HODS OF PREPARAT ION OF ET HYL
ALCOHOL
i) Ethyl alcohol is called grain alcohol as it is CH COOC 2 H 5  KOH ( aq )  CH 3 COOK  C 2 H 5 OH
3
obtained from starchy grains. (or)

ii) Ethyl alcohol is a constituent of wines and it is
R ' OH H2
called spirit of wine. RCOOH 
H
RCOOR '  RCH

catalyst 2
OH  R ' OH
iii) FROM ACETALDEHYDE:

i) Acetaldehyde forms ethyl alcohol when it is
reduced with a suitable reducing agent like
 CH 3  CH 2 
lithium aluminium hydride ( LiAlH 4 ) in ether..
ii) Acetaldehyde on catalytic hydrogenation also iii) Deprotonation to form alcohol
forms ethyl alcohol.
iii) The catalyst may be nickel, platinum, palladium
H
etc.
| 
CH 3CH 2 O  H  H 2 O
LiA / H 4 / ether or NaBH 4  
CH 3CHO 
or H 2 / Ni / pd / pt
 CH 3CH 2 OH
 CH 3  CH 2 OH  H 3O 
NaBH 4
RCOR ' 
 R  CH  R '
V. FROM GRIGNARD’S REAGENT AND
|
FORMALDEHYDE: Ethyl alcohol is obtained by
OH the action of methyl magnesium halide on
formaldehyde followed by hydrolysis
Pd
RCHO  H 2  RCH 2 OH
iv) CARBOXYLIC ACIDS are reduced to primary
alcohols with LiAlH 4 , a strong redusing agent.
i ) LiAlH 4
RCOOH   RCH 2OH
ii ) H 2O
v) FROM ETHYLENE (On large scale) ethylene is

formed in large quantities during CRACKING of
petroleum.
 Ethylene is passed into 98% conc. H 2 SO4
at 75  80 C under pressure to get ethyl
hydrogen sulphate ( C2 H 5 HSO4 ).

 This mixture is diluted with water and warmed
so that hydrolysis takes place to get alcohol.
H 2 C  CH 2  H 2 SO4  C 2 H 5 HSO4
C 2 H 5 HSO4  H 2O  C 2 H 5OH  H 2 SO4
MECHANISM INVOLVES THREE STEPS:
i) Protonation of alkenes to form carbocation by
 HYDROBORATION - OXIDATION METHOD:-
Alkenes undergo addition reaction with diborane.
electrophilic attack of H 3O  The addition compounds on hydrolysis.
 6  CH 2  CH 2   B2 H 6  2  CH 3CH 2 3 B

OH
  CH 3CH 2 3 B  3 H 2O  

CH 3  C H 2  H 2O 3CH 3CH 2 OH  H 3 BO3
ii) Nucleophilic attack of water on carbocation :
CH 3  CH  CH 2
CH 3  CH  CH 2   H  BH 2 2  | |
H BH 2
 CH 3  CH  CH 2
CH 3 CH CH 2
 CH 3  CH 2  CH 2 3 B    CH 3  CH 2  CH 2 2 BH  The solution is kept for 2-3 days at 300 C . Yeast
secrete invertase and zymase and fermenatation
takes place with these enzymes.
H 2O  3H O2 , OH 
2  Invertase converts sucrose intoglucose and
fructose while Zymase converts these products
3CH 3  CH 2  CH 2  OH  B  OH 3
into ethyl alcohol liberating CO2 as by product
Propan - 1 - ol
 Alcohol obtained in the process is called WASH
or WORT (6-10%)
 REDUCTION OF ALDEHYDES AND KETONES:  WASH is converted into 93-95% alcohol or
RECTIFIED SPIRIT by fractional distillation. And
Sodium borohydride  NaBH 4  is the convenient then into 100% alcohol or absolute alcohol by
reagent to carry out the reduction of aldehydes distilling rectified spirit with CaO and then calcium
or ketones into alcohol. gives absolute alcohol. Generally 95% aqueous
1) NaBH 4in alcohol
ethylalcohol is known as rectified spirit.
RCHO 2) H O 
 RCH 2 OH
3
RCOR ' 4

NaBH
 R  CH  R ' REACTIONS:
|  C 1 2 H 2 2 O 1 1  H 2 O  in
ve r ta s e
 
y ea s t
OH
C6 H12 O6 (glucose ) C6 H12O6 (fructose)
Pd
RCHO  H 2  RCH 2 OH
 C6 H 12O6 Zymase
 2C2 H 5OH  2CO2
 REDUCTION WITH LITHIUM ALUMINIUM
Yeast
Glu cos e or fructose
HYDRIDE LiAlH 4 better reducing agent for  FROM STARCH:
the conv ersion of carbonyl compounds,
carboxylic acids and their derivatives into  Starch  C6 H10O5 n is present in potatoes,
alcohols. wheat, barley, maize etc
LiAlH 4
R  COOH  4  H    RCH 2OH  H 2O
 Starch is made into solution by dissolving it in
water using steam under pressure.
FERMENTATION PROCESS : It is called mash.
 It is the process in which larger organic  Mash is mixed with malt(germinated Barley)
molecules slowly decomposed into simpler units extract so that at 50 C , the enzyme
in the presence of enzymes produced by micro
organisms. diastase.Present in malt converts starch into
maltose.
 It is an enzyme catalysed or biocatalysed organic
reaction. Yeast is a single celled micro organism  Maltose is cooled to 30 C and yeast is added.
 Ethyl alcohol is manufactured by the fermentation  Maltose and Zymase are the enzymes present
of either molasses or starch. yeast.
FROM MOLASSES :
 The enzyme MALTASE converts maltose into
Glucose while ZYMASE converts Glucose into
 The mother liquor left after crystallization of cane
Ethyl alcohol releasing CO2 .
sugar is called molasses. Molasses contain
sucrose upto 30.40%.  10% alcohol is obtained in the above process. It
 Molasses is diluted to 10% solution and is converted into rectified spirit or industiral
alcohol by fractional distillation and then into
acidified with H 2 SO4 antil pH is equal to 4.
absolute alcohol by distilling with CaO and then
 The above solution is transferred into fermentation
over calcium gives absolute alcohol (99.5% to
tank after adding yeast and required amounts of
ammonium Sulphate and ammonium phosphate 100% pure alcohol).
salts are added as food for yeast.
 The industrial alcohol or rectified spirit is

denatured to make it unfit for drinking. The O
denature alcohol is also called methylated spirit.
H H
There are two types of methylated spirits :
 1) Mineralised methylated spirit which is
H
90% rectified spirit, 9% methyl alcohol, 1%
CH 3  CH 2  CH 2  O
petrolum oil and a purple dye O
 2) Industrial methylated spirit which is 95%

H
rectified spirit and 5% methyl alcohol.
H
Reactions: O

H
n diastase n H
(C6 H10O5 ) n  H 2O  C12 H 22O11
2 malt 2
Starch Maltose
 A mixture of 96.5% ethyl alcohol and 4.4% water
is called constant boiling point mixture. It is also
O 1 1  H 2 O  Ma lt
a se
known as Azeotropic mixtaure it can be dried by
 C12 H 22  2 C 6 H 12 O 6
yeast
using anhydrous CaO and finally with Ca is used
Glucose to get 100% alcohol or absolute alcohol.

z y m a se
C 6 H 1 2 O 6    2 C 2 H 5 O H  2 C O 2
y ea st  It is soluble in organic solvents such as ether,
benzene etc.. in all proportions.
Ethyl alcohol
METHANOL PREPARATION :
CHEMICAL PROPERTIES :
Zno Cr2O3
CO  2 H 2 
200300 atm,573673 K
 CH 3OH  Ethanol (primary alcohol) under goes reactions
involving polar bonds ( O  H & C  O bond)
PHYSICAL PROPERTIES
 Ethyl alcohol is a colourless pleasant smelling  Alcohols react both as nucleophiles (due to
liquid and has burning taste. O  H bond cleavage) and electrophiles (due to
 It is inflammable and burns with a blue flame. C  O bond cleavage).
 Its boiling point is higher than corresponding  Alcohols can show two types of reactions due to
ether, alkyl halide and alkanes due to strong
cleavage of O-H bond or cleavage of C-O bond.
intermolecular hydrogen bonding.
 Compound MW/b.p (k)
CH 3CH 2OH 46/351
CH 3OCH 3 46/248
 REACTIONS INCVOLVING CLEAVAGE OF O-
H BOND :
REACTION WITH ACTIVE METALS:
CH 3CH 2 CH 3 44/231 Acidity of alcohols
 Its B.P is 78.10 C . Its Higher b.p is due to
Na  or  K 1
presence of inter molecular hydrogen bonding. C2 H 5OH   CH 3  CH 2  ONa  H 2
In alcohols, the boiling points decrease with 2
increase of branching in carbon chain (because  Acidic nature of alcohol is less than water due to
of decrease in van der Waals forces with electron releasing alkyl group
decrease in surface area).  __
R  O  H  O  H  R  O  H  OH 
. As the number of carbon atoms increase, the
boiling point of alcohols increase. This is due to base Acid Conjugate Conjugate
increase in vanderwaals forces of attractions. Acid Base
 Among isomeric alcohol b.p order is
6  CH 3 3 C  OH  2 Al 
primary > secondary > tertiary
Reason: Primary alcohol have more inter  2   CH 3 3  C  O  Al  3H 2
molecular force of attraction than in secondary 3
alcohol, which has more than in tertiary alcohol. Aluminium tert-butoxide.
 It is soluble in water in all proportions due to H- Conjugate basic strength are alkoxide ion is greater
bonding and contraction in volume occurs due than hydroxide ion
to evolution of heat.
Test Primary alcohol Secondary alcohol Tertiary alcohol

1) Lucas test : No reaction Reacts with in Reacts within
The alcohol is (No turbidity) 5 minutes to 30 seconds to give
treated with Lucas give turbidity turbidity
reagent
2) Victor Meyer’s : Red colouration Blue colouration No colour is produced

test : The alcohol is observed is observed R 3COH
is treated with red RCH2OH R 2CHOH  I 2  red P
phosphorous and  I 2 / red P  I 2  red P R 3CI
I 2 and the product RCH 2I R 2CHI  AgNO 2
is treated with  AgNO 2  AgNO 2 R 3CNO 2
AgNO2 and then RCH2 NO2 R 2CHNO2  HNO 2 & alkali
with nitrous acid  HNO 2  HNO 2 No reaction.
( NaNO2  H 2SO 4 )
and finally made (Nitrolic acid) (pseudo nitrol)
alkaline  alkali  alkali
red colouration blue colouration
3) Catalytic Aldehyde, H2 is Ketone, H2 is produced Dehydration takes place

dehydrogenation produced R2COH  giving alkene and H2O
RCH 2OH
with copper at 300 0 c R2CO  H 2 (CH 3 )3 COH 

CH 3  C  CH 2  H 2 O
1
CH 3
RCHO  H 2
(O )
 (
O )
( O)
4) Oxidation RCH 2OH 
 R 2CHOH 
 R3 C  OH 
with acidified R2CO Ketone + acid (O )
RCHO 
KMnO4  (O )  (O ) Mixture of acids
RCOOH Mixture of ketone contains lesser

same number alcohol and no. of carbons than .
of carbon atoms ketone contain alcohol. Acid contain still
in alcohol, same no. of lesser no. of carbons than
aldehyde and acid carbons but that of ketone.
acids contains
lesser no. of
carbons
 As number of electron releasing alkyl groups

increases acidic strength of alcohols decreases  REACTIONS INVOLVING CLEAVAGE OF
Among alcohols order of reactivity in the
reacations due to O-H bond cleavage is C  OH BOND :
Order of reactivity among alcohols in this type
CH 3OH  10 ROH  20 ROH  30 ROH
is 30  20  10  CH 3OH
CH 3OH  10 ROH  20 ROH  30 ROH (acidic
strength)  ACTION WITH PHOSPHOROUS HALIDE:
 Ethyl alcohol is neutral towards litmus paper,  3C2 H 5OH  PX 3  3C2 H 5 X  H 3 PO3
can not react with any base but liberates
hydrogen gas with sodium metal supporting Note : Basicity of H 3 PO3 is two, oxidation state
acidic nature of ethyl alcohol of phosphorous is 3
REACTION WITH ACETIC ACID AND ITS 
DERIVATIVES : C 2 H 5 OH  PX 5  C 2 H 5 X  POX 3  HX
C2 H 5OH  CH 3COOH  H 2O (X = Cl, Br)
 H 2 SO4
CH 3COOC2 H 5  H 2O  ACTION WITH THIONYL CHLORIDE

Pyridine ( C5 H 5 N )
C2 H 5OH  SOCl2   C2 H 5Cl
Note : In the above reaction H 2 SO4 acts as
catalyst and dehydrating agent.(FISCHER  SO2  HCl
ESTERIFICATION) (HCl is absorbed by pyridine)
 C2 H 5OH  CH 3COCl  CH 3COOC2 H 5
 ACTION WITH HYDROGEN HALIDE:
 HCl
 C 2 H 5OH   CH 3CO  2 O  Catalyst / 
C2 H 5OH  HX   C2 H 5 X  H 2 O
CH 3COOC2 H 5  CH 3COOH
zncl2
 C2 H 5OH  HCl 
Conc . H 2 So4
C2 H 5Cl  H 2O
Note : Order of reactivity HI > HBr > HCl > HF

 WITH CONC H2SO4 : (De hydration reactions)
Salicylic acid acetylasalicylic acid
0
(Aspirin) Conc.H 2SO 4 /100 110 C
C2 H 5OH   C2 H 5 HSO4
 H 2O
Note : In above reactions fruity odour ethyl acetate Ethyl hydrogen sulphate
is obtained which is use to recognise the OH Conc.H 2SO4 /140 C0
functional group.
2C2 H 5OH  
REACTION WITH NITRIC ACID : (Excess).
C2 H 5OC2 H 5  H 2O
C2 H 5OH  HONO2  C2 H 5ONO2  H 2O Diethyl Ether
(Ester of nitric acid)
H 2 SO4 ( excess ) /170C
C2 H 5OH   C2 H 4  H 2O
 REACTION WITH GRIGNARD REAGENT:
Ethylene
C2 H 5OH  RMgX  RH  C2 H 5OMgX
alkane  In the f ormation of ethylene, ethyl
hydrogensulphate and diethyl ether are
C2 H5OH  CH3MgI  CH4  Mg(OC2H5 )I intermediate compounds.
 ACTION WITH ALUMINA : (Dehydration)  IODOFORM REACTION :
0
C2 H 5OH 
Al 2 O3 / 350 C
 CH2 = CH2  H 2O C2 H 5OH  4 I 2  6 KOH  CHI 3  HCOOK
Al 2 O3 / 2600 C under pressure Iodoform
2C2 H 5OH   C2H5OC2H5
5 KI  5 H 2O
+H2O
Note : CHI 3 is yellow crystalline solid.
OH
|
85% H 3 PO4
 Among primary alcohols only Ethyl alcohol and
CH 3 C HCH 3   among secondary alcohols only 2-alkanols can give
 440 K
iodoform reaction. Where as all tertiary alcohols
CH 3  CH  CH 2  H 2O can not give this reaction.
REDUCTION :
20% H PO
 CH 3 3 C  OH 
358 K
 3 4
Re d P
C2 H 5OH  2 HI 
Heat
 C2 H 6  H 2O  I 2
CH 3  C||  CH 3  H 2 O MECHANISM OF DEHYDRATION :
CH 2 IT TAKES PLACE IN THREE STEPS :
Thus, the relative ease of dehydration of alcohols i) CH 3  CH 3  OH  H 2 SO4 

follows the following order. ..
Tertiary > Secondary > Primary CH 3  CH 2   O|  H  OSO3 H
OXIDATION REACTIONS:
H
1. Oxidation with KMnO4 and K 2Cr2O7 ii) Formation of carbonation. It is the slowest step or
H 2So 4 / KMno 4 orK 2 Cr2 O7 rate determining step.
C2 H 5OH  (o)

..
CH3CHO  CH3COOH(O) CH 3  CH 2   O|  H  ..

 CH 3  C H 2  H 2 O :
H
 CrO3
RCH 2OH   RCHO
PCC
iii) Elimination of proton to get alkene
CH 3  CH  CH  CH 2OH  
CH 3  CH  CH  CHO
CrO3
R  CH  OH   R '   RCO  R '
Sec-alcohol Ketone Since the rate determining step is the formation of
2. DEHYDROGENATION: (Oxidation) carbocation, the rate of dehydration is directly
Re d hot 'Cu ' / 3000 C
proportional to the formation of carbocation. Since
C2 H 5OH   CH3CHO+H2 the stability of carbocation is
 Cu
RCH  OH   R ' 
573 K
 RCO  R ' 30  20  10 , the order of dehydration of alcohols
is
Cu
 CH 3 3 C  OH 
573 K
 CH 3 C|  CH 2
 CH 3 3 COH   CH 3 2 CHOH  CH 3  CH 2OH
CH3
 REACTIONS INVOLVING ALKYL GROUP AND Dehydration of 10 alcohol requires 95% H 2 SO4
ALCOHOL GROUP :
at H 2 SO41700 C , 20 alcohol requires 75%
 REACTION WITH CHLORINE :
C2 H5OH  Cl2  Cl2
CH3CHO  CCl3CHO H 2 SO4 at 1000, where as 30 alcohol requires
Chloral 5% H 2 SO4 at 500 C .
 ACTION WITH BLEACHING POWDER :
Re flux ed with  The dehydration of 1o alcohol goes by E 2 mech
C2 H 5OH 
CaOCl 2 / OH 
 CHCl3 + Ca(CH 3COO) 2
o
Chloroform Cal.Acetate
nism, but that of 2o and 3 alcohols go by E1
mechanism.
When more than one product is formed, the 5. A preservative for biological specimens, an
major product is according to Zaitsev’s rule. It antifreeze for automobile radiotors, a fuel in spirit
states that hydrogen is removed from   carbon lamps, stoves, a petrol substitute known as power
alcohol.
that is bonded to the least number of hydrogen
PERPARATION OF WINE
atoms.(  -elimination)
Grapes are the source of sugar and yeast.
Eg. Dehydration of 2-butanol predominantly gives
Sugar increases in ripe grapes and yeast grows
2-butene.
on the outer skin. On crushing the grapes, sugar
Conc
CH 3  CH 2  CHOH  CH 3 
H 2 SO4
 and enzyme come in contact and fermentation
starts in anaerobic conditions. If air is present it
CH3  CH  CH  CH3  CH3  CH2  CH  CH2 oxidises alcohol to acids
2-butene(major) 1-butene LEVEL -1
(minor) MODEL QUESTIONS
 FORMATION OF ADDTION COMPOUNDS : NOMENCLATURE
Ethyl alcohol reacts with anhydrous metal salts 1. 2,4-dimethyl -3-pentanol is a
to form addition compounds (that is alcohol of 1) primary alcohol 2) secondary alcohol
crystallisation) 3) tertiary alcohol 4) dihydric alcohol
2. Which of the folllowing is a tertiary alcohol
a) C2 H 5OH .3CaCl2 , C2 H 5OH .6MgCl2 ,
(2000E)
C2 H 5OH .3CuSO4 1)  CH 3 2 CHCH 2 OH
2) CH 3CH 2CH 2CH 2OH
3) CH 3CH 2CH 2OH 4)  CH 3 3 COH
USES OF SOME IMPROTANT COMPOUNDS
3. Which of the following is tertiary alcohol
(METHANOL AND ETHANOL) 1) Ethyl alcohol 2) Isopropyl alcohol
METHANOL 3) Neopentyl alcohol 4) 2-methyl 2-propanol
4. Glycerol does not contain ........ alcoholic group
1. Methanol a colourless liquid with b.pt. 670 C is 1) 10 2) 20 3) 30 4) 10 and 20
used as solvent, paints, varnishes, shellac etc., 5. Which one of the following compound is an
2. Used in the manfacture of HCHO, perfumes and isomer of 1-butanol (2001M)
dyes. 1) 2-methyl-2-butanol 2) 1-methyl-2-butanol
3. Used in the preparation of methylated spirt, a 3) 3-methyl-2-butanol 4) 2-methyl-1-propanol
mixture of recatified spirit (95.6% ethyl alcohol +
4.4%water) and methyl alcohol making ethyl 6. The number of 10 , 20 and 30 alcoholic groups in
alcohol unfit for drinking . Mannitol or Sorbitol are
4. Two types of methylated spirits: 1) 2, 4 and 0 2) 1, 4 and 0
a) mineralised spirit = 90% rectified spirit + 9% 3) 2, 2 and 0 4) 2,1 and 1
methyl alcohol + 1% pyridine 7. Glycerol contains
1) Two secondary and one primary alcoholic
b) Surgical spirit = 95% rectified spirit + 5% MeOH groups
5. In denaturation of ethyl alcohol copper sulphate is 2) One secondary and two primary alcoholic
added to give colour and pyridine is added to make groups
it a foul smelling liquid. Because of denaturation 3) Three secondary alcoholic groups 4) T hree
alcohol becomes unfit for drinking. primary alcoholic groups
USES OF ETHYL ALCOHOL 8. Which one of the following pairs of compounds
1. As a solvent for pharmaceutical preparations, are functional isomers (2001E)
paints, perfumes, varnishes, gums etc., 1) CH 3CH 2CH 2 OH , CH 3CHOHCH 3
2. In alcoholic bevarages. 2) CH 3CH 2 CH 2OH ,  CH 3  2 CHCH 2 OH
3. As reaction medium, extractant and crystallsing 3) CH 3CH 2CH 2 OH , CH 3CH 2CH 2Cl
4. A source for the preparation of acetaldehyde, 4) CH 3CH 2CH 2OH , CH 3OCH 2 CH 3
chloral, chloroform, iodoform, acetic acid ether etc.
22. Ethyl alcohol is the hydrolysis product of
NOMENCLATURE 1) C2H5Cl 2) CH3CHO
9. Primary alcoholic group is 3) C2H4 4) C2H5 MgI
1) -CH2OH 2) >CHOH 23. Which of the following enzyme converts maltose
3) >CHOH 4) >C=O to glucose
10 2-methyl pentanol-1 is a 1) Invertase 2) Zymase 3) Maltase 4) Diastase
1) 10 alcohol2) 20 alcohol3) 30 alcohol4) enol 24. Absolute alcohol is prepared from rectified spirit
11. Spirit of wine is the common name of by
1) CH3OH 2) C2H5OH 1) Steam distillation 2) Fractional distillation
3) HCHO 4) CH3COCH3 3) distillation with CaO &Ca 4) Simple distillation
12 CH2OH 25. Diastase enzyme converts _________ to
| _________
CH2OH is a 1) Glucose to ethy alcohol
1) 10 alcohol 2) 20 alcohol 2) Starch to maltose
0
3) 3 alcohol 4) Carbinol 3) Maltose to glucose
13. The IUPAC name of sec. butyl alcohol is 4) Sucrose to glucose
1) 1-butanol 2) 2-butanol 26. The enzyme not produced by yeast
3) 2-methyl-l-butanol 4) 2-methyl-2-butanol 1) Diastase 2) Maltase
14. CH2OH—CHOH—CH2OH is glycerol. 3) Zymase 4) Invertase
It doesn't contain ------------ alcoholic group 27. Germinated barley seeds are called malt is a
1) 10 2) 20 source of an enzyme called
3) 30
4) both 10 & 20 1) Zymase 2) Diastase
15. An example for a polyhydric alcohol is 3) Maltase 4) Invertase
1) Methyl alcohol 2) Neopentyl alcohol 28. Which is an antifreeze ?
3) Sec butyl alcohol 4) Mannitol 1) water 2) ether 3) ethyl alcohol 4) aniline
16. Which one of the following is a secondary 29 Ethyl alcohol containing 9.5% methyl alcohol and
alcohol (2002E) 0.5% pyridine is called
1) 2-methyl-2-propanol 2) 1-propanol 1) Spirt 2) Denaturated spirit
3) 1-butanol 4) 2-pentanol 3) Rectified spirit 4) Absolute alcohol
17. An isomer of ethanol is [I.I.T. 1986] 30. Breaking of big Organic molecules in the presence
1) methanol 2)dimethyl ether of enzymes is called
3) acetone 4) diethyle ether 1) Cracking 2) Pyrolysis
18. The IUPAC name for 3) Fermentation 4) Oxidation
CH3– CH2 – CH(OH) – CH = CH2 (1993) 31 Primary alcohol can not be prepared by the
1) 2-methyl butyl alcohol reduction of
2) 2-methyl butanol - 1 1) aldehyde 2) acid 3) ketone 4) Ester
3) Pent-1-ene-3-ol 32. The two enzymes present in yeast that are
4) 2- methyl butanol and - 2- ol responsible for the formation of ethylalcohol from
19. Total number of isomeric alcohols with formula molasses in the fermentation process are
C 4 H 10O is [M.L.N.R. 1986] (1999)
1) Invertase, zymase
1) 2 2) 1 3)3 4)4 2) Invertase, diastase
PREPARATION METHODS OF 3) Zymase, diastase
ETHYL ALCOHOL 4) Invertase, maltase
20. The enzyme which converts glucose to
ethylalcohol is (1989) PRACTICE QUESTIONS
1) zymase 2) invertase PREPARATION METHODS OF
3) maltase 4) diastase ETHYL ALCOHOL
21. W hichof thef ollowing is Lucas reagent
(2000E) 33. During the fermentation of molasses the optimum
1) ammonical silver nitrate 2) Br2 / CCl4 pH maintained is
1) 4 2) 2 3) 7 4) 10
3) dry ZnCl2 / con. HCl 4) alk.KMnO4 34. The amount of water present in rectified siprit is
1) 4.4 % 2) 10% 3) 95% 4) 80%
35. C2H5OH ——> C2H5Br. In this conversion the 45. Which alcohol is prepared from water gas?
reagent is (1994)
1) HBr 2) Br2 + CCl43) Br2 water 4)KBr 1) C2H5OH 2) CH3CH2CH2OH
36 Ethylalcohol is manuf actured by the 3) CH3OH 4) C6H5CH2OH
fermentation of (1985) PHYSICAL AND CHEMICAL PROPERITES
1) molasses 2) starch 3) both 46. 95% et hyl a l cohol c an be c onv ert e d t o
4) none 100% e t hyl al cohol by t he f ol l owi ng
37. Ethyl alcohol is manufactured from ethylene by 1) Magnesi um chl ori de
1) Permanganate 2) Catalytic oxidation 2) Cal cium oxi de
3) Absorption into Conc. H2SO 4 followed by 3) Magni si um phosphat e
hydrolysis 4) Reduction 4 ) Ma gne si um su l p ha t e
38. Conversion of glucose to ethyl alcohol can be 47. W a s h o r w o r t p o s s e s s e s t h e - - - -
carried by percent age of et hyl alcohol
1) Lactose 2) Invertase 1) 95% 2) 100%
3) Zymase 4) Diastase 3) 66. 9% 4) 6 - 1 0%
39. An enzyme which brings about the conversion 48. CaC l 2 + C 2 H 5 O H —> CaCl 2 . x . C 2 H 5 OH
of starch into maltose is known as 1) 3 2) 6 3) 2 4) 1
1) Diastase 2) Zymase LEVEL-II
3) Maltase 4) Invertase PREPARATION METHODS
40. Which is the catalyst in the convertion of water 49. Pr i m ary a l co ho l s ar e o bt ai n ed by t he
gas and hydrogen into ethyl alcohol ? react i on of G ri gnard reagent wi t h
1) MnO 2) raney Ni 1) CH 3 COCH 3 2) HCO OH
3) Fe 4) ZnO-Cr2O3 3) HCHO 4) CH 3 CHO
41. The following substance can be used as a raw 50. Ma sh i s
material for obtaining alcohol 1) Germinate barley seed powder
1) Potatoes 2) Molasses 2) Fermented molasses
3) Maize 4) All 3) Steam heated starch paste
42. The Gas liberated during fermentation is 4) Raw starch
1) alcoholic vapours 2) Hydrogen 51. Enzymes involved used in the fermentation of
3) CO 4) CO2 cane sugar to alcohol?
43. Assertion (A): In the fermentation process of 1) Diastase, invertase 2) Invertase, zymase
mol asses, along wi th yeast (NH 2 ) 2 SO 4 , 3) Diastase, zymase 4) Maltase, zymase
(NH4)3PO4 is added. PHYSICAL AND CHEMICAL PROPERTIES
Reason(R): (NH4)3PO4 and (NH2)2SO4, acts as 52. Concentration. of C2H5OH is not possible beyond
food and helps the growth of yeast. 95% by simple distillation.Because
1) Ether is formed 2) Azeotrope is formed
1) Both A and R are true and R is the correct
3) C2H5OH and H2O react
explanation to A
4) H-bonding takes palce
2) Both A and R are true and R is not the correct 53. Which of the following gives ethyl alcohol by the
explanation to A action of Methyl magnesium halide followed by
3) A is true but R is false 4) A is false but R is hydrolysis
true 1) formaldehyde 2)acetaldehyde
44. Assertion (A): Alcoholic fermentation involves 3) acetic acid 4) methyl alcohol
conversion of sugar into ethanol by the action of 54. When wine is put in air it become sour due to
yeast. 1) Oxidation of C2H5OH into CH3COOH
Reason(R): Fermentation involves the liberation 2) Bacteria
of CO2 gas. 3) Virus 4) Formic acid formation
1) Both A and R are true and R is the correct 55. Which of the following are correct?
i) Ordinary ethyl alcohol is known as grain
explanation to A
alcohol.
2) Both A and R are true and R is not the correct
ii) methylated spirit contains rectified spirit.
explanation to A iii) Absolute alcohol is 100% C2H5OH
3) A is true but R is false 4) A is false but R is iv) rectified spirit.is 100% ethanol.
true The correct statement is
1) ii, iii, iv 2) ii, iii 3) i, ii, iii 4 ) all are correct
56. Absolute alcohol cannot be obtained by simple 64. Which of the following compound is formed when
fractional distillation because [C.P.M.T 1982] ethonol reacts with acetic acid in the presence
1) pure C2 H 5OH is unstable
of conc.H 2 SO4
2) C2 H 5OH formshydrogenbonding with water
3) Oxidation 1) CH 3COOC2 H 5 2) C2 H 5OC2 H 5
4) it is a azeotropic mixture with water. 3) C H 3OC H 3 4) CH 3CHO
57. When CH 3 MgI is made to react with acetone
65. Primary,secondary and tertiary alcohols are dis-
and addition product is hydrolysed we get tinguished by
1)primary alcohol 2)secondary alcohol 1) oxidation method 2) Lucas test
3)tertiary alcohol 4) an aldehyde 3) Victor Meyer’s method4)all the above
58. Ethanol and Methanol are miscible in water due 66. Which of the following soluble in water
to 1) CH 3OH 2) CHCl3
1) Dissociation of water
2) Their Acidic character 3) CCl4 4) CS 2
3) Allyl Groups 67. Which C2 H 5OH is heated with acidified
4) Hydrogen bonding
59. To bring about dehydration of alcohols we can K 2Cr2O7 it forms CH 3COOH . It is an ex-
use
ample of .
1) Conc. H 2 SO4 2) Al2 O3 1) Molecular rearrangement 2) Hydrolysis
3) Oxidation 4) Dehydration
3) CaO 4) both 1,2 68. The reaction between an alcohol and carboxylic
60. In the esterfication reaction conc. H 2 SO4 act as. acid leads to the formation of
1) Aldehyde 2) Ester
1) catalyst
3) Ketone 4) Paraffins
2) dehydraing agent
69. Ethyl alchol on heating with HI in presence of
3) Oxidizing agent
ZnCl2 yields
4) both 1,2
1) Ethane 2) Ethyl Iodide
61. Lucas reagent
3) Ethylene 4) Methane
1) Conc. HNO3 + anhydrous Mgcl2 70. Alcohol beverages contain
1) Glycerol 2) Ethyl alcohol
2) dil.HCl+ anydrous Zncl2 3) Methyl alcohol 4) Isopropyl alcohol
71. The first oxidation product of a primary alcohol is
3) Conc. HNO3 +anhydrous Zncl2
1) acid 2) aldehyde 3) ketone 4) ether
4) Conc.HCl+anhydrous Zncl2 72. Ethyl alcohol on oxidation with acidfied K2Cr2O7
gives
Zncl2
C2 H 5OH  HCl  1) CH3COCH3 2) HCOOH
62. 0  C2 H 5Cl  H 2 O.
200 c 3) CH3COOH 4) HCHO
in this reaction anhydrous Zncl2 act as. 73. Ethyl alcohol can be distinguished from n-propyl
1) dehydrating agent alcohol by using.
2) dehydrogenating agent 1) Lucas reagent 2) I2 + NaOH
3) dehalogenating agent 3) Na metal 4) Bosches reagent
4) dehydrohalogenating agent 74. Regarding ethyl alcohol the wrong statement is
63. Which of the following reaction conditions are 1) It is neutral to litmus
2) It gives yellow crystalline ppt with I2 + dil.
used for the conversion of ethanol to ethylene.
NaOH
1) conc. H 2 SO4 / 700 c 2) dil. H 2 SO4 /140 0 c 3) It gives a product of fruity odour on reaction
with CH3COOH
3)dil. H 2 SO4 /100 0 c 4) conc. H 2 SO4 /170 0 c 4) It gives turbidity spontaneously on the addition
of Lucas reagent.
0 0 0
75. 1 , 2 and 3 alcohols may be distinguished from 86. Which of the following alcohols reacts most
one another by readily with Lucas reagent [P.M.T(M.P.)1986]
1) Oxidation method 2) Action of hot HI
1) CH 3CH 2 CH 2 OH 2) (CH 3 ) 2 CHOH
3) Lucas reagent 4) Both 1 and 3
76. C2H5OH + HONO2  A + H2O. “A” is 3) (CH ) COH 4)CH3CH2OH
3 3
1) Ester 2) Ether 3) Alcohol 4) Alkane
0
77. With, which one of the following reagents 87. CH 3  CH 2  OH Conc
 . H 2 SO4 / 170
 X . Then
O  H bond fission in alcohol can not takes "X" is
place 1) C2H4 2) Isopropyl alcohol
1) Na 2) CH 3COOH 3) CH 3 MgBr 4) PCl5
3) Neopentyl alcohol 4) 2-Methyl 2-propanol
78. Alcohols can be oxidized to carboxylic acids by
1) alkaline KMnO4 2) acidified K 2Cr2O7 88. C2H5OH + PCl3 —> C2H5Cl + X. Here X is an oxy
acid of phosphorus X is
3) conc. HNO3 4) all of these 1) H3PO4 2) H3PO3 3) H3PO2 4) HPO3
79. The highest boiling point is for
PRACTICE QUESTIONS
1) C2 H 5OH 2) C2 H 5Cl 89. C2H5OH + I2 + KOH —> CHI3 + KI +X
3) C2 H 6 4) CH 3OCH 3 Here the missing product X is
80. C 2H 5 OH ——> C 2H 5 —O—C 2 H 5 . In this 1) HCOOK 2) CH3COOK
conversion the reagent is 3) (CH3COO)2Ca 4) (HCOO)2Ca
90. Whichof the following pair of reagents produces
1) Al2O3 at 2500C 2) Concn. H2SO4 at 1700C
same product with ethyl alcohol
3) Conc. H2SO4 at 1100C 4) Al2O3 at 3500C 1) Conc. H2SO4 1700C, Cu-3000C
81. The intermediate product in the preparation of 2) Conc. H2SO4 - 1700C, Conc. H2SO4 - 1400C
ethylene from ethanol and H2SO4 is (1986) 3) Conc. H2SO4 - 1000C, Al2O3 - 3500C
4) Conc. H2SO4 - 1700C, Al2O3 - 3500C
1) C2H+5 2) C2H4
91. An organic compound reacts with carboxylic acid
3) C2H5HSO4 4) C2H5O+H2 in presence of dehydrating agent to form an
82. When C2H5OH vapours is passed over red hot ester,the compound may be
copper at 3000C the product formed is (1987) 1) Aldehyde 2) Ester
1) CH3CHO 2) CH3COCH3 3) Alcohol 4) Ketone
3) C2H4 4) CH3COOH 92. The reaction R—OH + HCl  R—Cl + H2O is
83. Ethyl alcohol on distillation with X gives reversible, so for the the completion of the
reaction we use along with the reactants.
chloroform, X is (1992)
1) Conc. H2SO4 2) P2O5
1) a paste of bleaching powder 3) H3PO4 4) N2O5
2) chlorine X
3) methyl chloride 93. C2 H 5OH 
3600 C
 C2 H 4 what is ‘X’?
4) Ca (OH)2 1) Acidic oxide of phosphorous
84. Ethyl alcohol when passed over copper at 3000C 2) Amphoteric oxide of zinc
is dehydrogenated to give (1992) 3) Basic oxide of calcium
4) Amphoteric oxide of aluminium
1) acetone 2) acetaldehyde
94. Which one of the following reagents can not
3) ether 4) ethylene
cause C  O bond fission in alcohols
85. The reagent used for converting ethanoic acid
to enthanol is (1998) 1) HCl /ZnCl2 2) PCl5
1) LiAlH4 2) BH3
3) SOCl2 4) Sodium
3) PCl3 4) K2Cr2O7/H+
95. An Organic compound dissolved in benzene and 105. Assertion (A): CaCl2 can’t be used for drying
evolved hydrogen with sodium. It is ethyl alcohol
1) Ketone 2) An aldehyde Reason (R) : Calcium chloride can form an
3) A tertiary amine 4) An alcohol addition compound with ethyl alcohol
96. Which group can be completely displaced by a 1) Both A and R are true and R is the correct
explanation to A
Halogen group?
1) Hydroxyl group(OH) 2) aldehyde (-CHO) group
explanation to A
3) nitro (-NO2) group 3) A is true but R is false
4) Keto (C=O) group 4) A is false but R is true
97 Ethyl alcohol is treated with chlorine. The final 106. Assertion (A): Ethyl alcohol is soluble in organic
product obtained is solvents
1) CH3CHO 2) CCl3—CHO Reason (R) : Ethyl alcohol is having non polar
3) CHCl3 4) CCl4 ethyl group.
98. 23 mg of Na metal is placed in excess of alcohol. explanation to A
Which alcohol can produce more amount of H2 2) Both A and R are true and R is not the correct
gas. explanation to A
3) A is true but R is false 4) A is false but R is
1) CH3OH 2) C2H5OH
true
3) C3H7OH 4) Same for all
107. Assertion (A): Alcohols on dehydration can
99. On oxidation with acidified K2Cr2O7 a compound produce ether as well as alkene under different
gives a Ketone containing same no. of carbon conditions.
atoms. The substance is Reason(R): Dehydration of alcohol proceeds
1) aldehyde 2) 10 alcohol through formation of carbonium ion.
0
3) 2 alcohol 4) Both 10 and 20 alcohols 1) Both A and R are true and R is the correct
100 Which alcohol is most reactive towards HCl in explanation to A
the presence of anhydrous ZnCl2 ? explanation to A
3) A is true but R is false 4) A is false but R is
1) primary 2) secondary
true
3) tertiary 4) all of these
108. When ethylalcohol reacts with Br2 in presence
101. Primary, secondary and tertiary alcohol cannot of red phosphorus the compound formed is
be differentiated by (1992)
1) reduced Cu 2) acidified KMnO4 1) C2H6 2) PBr3 3) CH3Br 4) C2H5Br
109. The alcohol that produces turbidity immediately
3) Lucas reagent 4) PCl3 with ZnCl2 and Con. HCl at room temperature
(1997)
102 Isopropyl alcohol on oxidation forms 1) 1-hydroxybutane
1) ethylene 2) Acetone 2) 2-hydroxybutane
3) Ether 4) Acetaldehyde 3) 2-hydroxy-2-methyl propane
103. When tertiary butyl alcohol is passed over 4) 1-hyrdoxy-2-methyl propane
reduced copper, the reaction taking place is 110. In the following reaction X and Y respectively
1) oxidation 2) reduction (2002E)
3) dehydration 4) substitution KMnO4 / H 
Y / H 2 SO4
104. Assertion (A): Ethanol is miscible in all C2 H 5OH  X  
proportions with water
CH 3COOC2 H 5
Reason (R) : Hydrogen bond is formed between
water and alcohol molecules. 1) CH 3OH , C2 H 5OH
2) Both A and R are true and R is not the correct 2) CH 3CHO, CH 3OH
explanation to A
3) A is true but R is false 3) CH 2  CH 2 , CH 3COOH
4) A is false but R is true
4) CH 3COOH , C2 H 5OH
111. W hat are X and Y in t he reacti on, 119. Iodoform cannot be prepared form
0
80 C H 2O / 
C2 H 4  H 2 SO4   X  Y 1) CH 3OH 2) C2 H 5OH
(2004 M)
3) CH 3CHO 4) CH 3COCH 3
1) C2 H 6 , C2 H 5OH 2) C2 H 4 , C2 H 5 SH
120. Ethylo alcohol forms CaCl2, XC2H5OH; MgCl2,
3) C2 H 5OSO3 H , C2 H 5OH YC2H5OH ane CuSO4, ZC2H5OH when C2H5OH
reacts with respective anhydrous salts. Then
4) C2 H 2 , CH 3CHO
1) X =3, Y = 3, Z = 2
112. Hydrogen chloride and SO 2 are the side 2) X =3, Y = 6, Z = 3
products in the reaction of ethanol with thionyl
3) X =3, Y = 7, Z = 4
chloride. Which of the following is main product
in this reaction. (2005 M) 4) X = 4, Y = 4, Z = 4
121. Which of the following on oxidation gives ketone
1) C 2 H 5  O  C2 H 5 2) C 2 H 6
1) CH3—CH2—CH2—OH 2) CH3—CH2—OH
3) CH 3Cl 4) C2 H 5 Cl 3) CH3—CHOH—CH—CH3
113 The molecular f orm ula of X is : 4) CH 3  CH  CH 2  OH
0
Cu / 300 C
C 2 H5 OH  X (2005 E) |
OH
1) C 4 H 6 O 2) C 4 H10 O
Pd  BaSO4 / Quinoline
122. H  C  CH  H 2  A
3) C2 H 4 O 4) C 2 H 6 O
114. Hydrogen bonding is maximum in [I.I.T. 1987] HCl KOHaq
 B  C
1) ethanol 2) diethyl ether
3) ethyl chloride 4) triethyl amine Here the ‘C’ is
1) Propane 2) Ethanol
LEVEL-III 3) Ethyne 4) Ethylene
MODEL QUESTIONS PBr3 alc. KOH
115. When ethyl alcohol is distilled with bleaching
123. (A) ————> (B) —————>
powder and water then chloroform is obtained.
The no. of moles of bleaching powder needed conc. H SO
(C)  A
2 4
H2O,75800 c
in the preparation of one mole of chloroform is
1) 10 2) 5 3) 4 4) 2 Here A in the above sequence is
116. CH3OH + PCl3 —> 1) ethanol
KCN hydrolysis
A   B    C .Then "C" is 2) Ethyl chloride
1) CH3CH2OH 2) CH3CHO 3) ethane
3) CH3COOH 4) CH2OH-CH2OH 4) acetic acid
117. An organic liquid A containing H and O has a 124. Compound A reacts with Na metal to give B. A
pleasant odour with a b.pt of 780C on boiling A also reacts with PCl5 to give C. B and C reacts
with conc. H2SO4 a colourless gas is produced with each other to give dimethyl ether. Then A,
which decolourises bromine water and alkaline B and C respectively are
KMnO4. One mole of this gas also takes one 1) CH3OH, CH3ONa, CH3COCl
mole of H2. The organic liquid A is
2) CH3OH, CH4, CH3Cl
1) C2H5Cl 2) C2H5CHO
3) CH3OH, CH3ONa, CH3Cl
3) C2H6 4) C2H5OH
4) CH3Cl, CH4, CH3OH
118. A compound reacts with sodium and liberates
125. A compound (X) of molecular formula C3H8O can
hydrogen and on oxidation gives ketone. The
be oxidized to a compound of molecular C3H6O2
formula of the compound could be.
(C), (X) is most likely to be.
1) CH3CH2OH 2) CH3CHOHCH3
1) Aldehyde 2) Alcohol
3) CH3CH2CH2OH 4) CH3CH2 CH2CH2OH
3) Ether 4) Both 2 and 3
126 In the sequence of reactions (Z) is PRACTICE QUESTIONS
moist Ag2O 0
Conc.H2SO4at170 C
134. In the following sequence of reactions the end
C2H5Br  (X)  (Y) product is
2
HBr H 2 SO4 / Hg CH 3 MgCl
  (Z) CH 3C  CH 
H O / 60 0 C
 A 
H 2O
B
2
1) ethylene bromide 2) ethylidene bromide 1) Acetone 2) Tertiary butyl alcohol

3) ethyl bromide 4) vinyl bromide
3) Secondary propyl alcohol 4) Ethyl alcohol
127. I2 produced when ozone reacts with moist KI is
135. Which of the following can participate in both
used to convert C2H5OH to CI3CHO. Number of
moles of ozone required to convert 1 mole of of esterification and idoform reactions
C2H5OH into CI3CHO is 1) Acetic acid 2) Acetal dehyde
1) 1 2) 2 3) 4 4) 3 3) Acetone 4) Ethyl alcohol
128 Which of the following gives Iodo form test 136. Assertion (A): The boiling point of C2H5OH is
1) CH3—CH2—CH2—OH 2) CH3—CH2—OH less than that of H2O though the molecular weight
3) CH3—CH(OH)—CH3 4) Both 2 and 3
of C2H5OH is more than that of water.
129. The compound B formed in the following
Reason (R) : C2H5OH molecules are not highly
sequence of reaction is
associated through hydrogen bonding as in water.
CH 3CH 2CH 2OH PCl
3  A AlcNaOH
  B 1) Both A and R are true and R is the correct
1) Propane 2) Propanol explanation to A
3) Propene 4) Propyne 2) Both A and R are true and R is not the correct
130. A compound "X" of the formula C3H8O gives explanation to A
iodoform test. On oxidation with acidified K2Cr2O7,
3) A is true but R is false4) A is false but R is true
X gave Y. Y also gives iodoform test then X and
Y are 137. Assertion (A): Dehydration of alcohols can be
1) CH3CH2CH2OH, CH3CH2CHO carried out with Conc H 2SO 4 but not with
2) CH3CHOHCH3 ,CH3COCH3 conc.HCl.
3) CH3CH2CHO, CH3CH2CH2OH Reason (R) : H2SO4 is dibasic which HCl is
4) CH3COCH3, CH3CHOHCH3 monobasic.
131 Vapour density of an organic compound is 23. It 1) Both A and R are true and R is the correct
contains 52.17% of carbon and 13% of hydrogen.
explanation to A
The compound gives iodoform test. The
compound is 2) Both A and R are true and R is not the correct
1) Ethanol 2) Dimethyl ether explanation to A
3) Acetone 4) Methanol 3) A is true but R is false
132. There are three alcohols x,y,z which have 2,1 4) A is false but R is true
and 0 alpha hydrogen atom(s) respectively. 138. Which one of the following reagents is useful in
Which does not give Lucas Test immediately
converting 1-butanol to 1-bromobutane? (1989)
1) x 2) y
1) CHBr3 2) Br2 3) CH3Br 4) PBr3
3) z 4) all the three do not give test
133. Two organic compounds A and B react with 139 Which of the following are the starting materials
sodium metal and release H2 gas. A and B react for the Grignard’s synthesis of t-butanol? (1989)
with each other to give ethyl acetate. The A and 1) CH3MgBr + CH3COCH3
B are 2) CH3CH2MgBr + CH3COCH3
1) CH3COOH and C2H5OH
3) CH3MgBr + CH3CHOHCH3
2) HCOOH and C2H5OH
4) CH3MgBr + (CH3)3CH
2) CH3COOH and CH3OH
4) CH3COOH and HCOOH
140 Ethanol when reacted with PCl5 gave A, 147. The treatment of a compound with HIO4
POCl3 and HCl . A reacts with silver nitrate
to form B (major product) and AgCl . A and B produces CH 3CHO and CH 3CH 2CHO.
are respectively
1. CH 3CH  CHCH 2CH 3
1) C2 H 5Cl , C2 H 5OC2 H 5
2) C2 H 6 , C2 H 5OC2 H 5 2. CH 3CH (OH )CH (OH )CH 2CH 3
3) C2 H 5Cl , C2 H 5ONO 3. CH 3CH  CHCH  CH 2
4) C2 H 6 , C2 H 5ONO
4. CH 3CH (OH )CH 2 CHO
141. 3 moles of ethanol reacts with 1 mole of
phosphorous tribromide to form 3 moles of PRACTICE QUESTIONS
bromoethane and 1 mole of X. X is 148. A molecule consumes 2 molecules of HIO4
(2001E) The number of carbon-Carbon bond broken by
1) H 3 PO4 2) H 3 PO2 3) HPO3 4) H 3 PO3 this acid is
LEVEL-IV 1. One 2. Two 3. Three 4. None
MODEL QUESTIONS 149. An industrial method of preparation of methanol
is
142. The order of reactivity of alcohols towards Na
1. Catalytic reduction of carbon monoxide in
or K metal is
1. Primary > Secondary > Teritiary presence of Zno  Cr2O3
2. Primary < Secondary < Teritiary
3. Primary < Secondary > Teritiary 2. By reacting methane with stem at 900 0 C
4. Primary > Secondary < Teritiary with a nickel catalyst
143. Oxymercuration-demercuration of 3. By reducing formablehyde with lithium
aluminium hydride
CH 3CH  CH 2 produces. 4. By reacting formaldehyde with aqueous
sodium hydroxide solution
1. CH3CH2CH2COH 2. CH 3CH  OH  CH 3
150. The compound which gives the most stable
carbonium ion on dehydration.
3. CH 3CH  OH  CH 2OH 4. CH 3COCH 3
CH 3 CH CH 2OH
144. Hydroboration-Oxidation of CH 3CH  CH 2 1.
CH 3
produces.
1. CH 3CH 2CH 2OH 2. CH 3CH  OH  CH 3 CH 3
CH 3 C OH
3. CH 3CH  OH  CH 2OH 2.
CH 3
4. CH 3COCH 3
145. The order of reactivity of dehydration of alcohol 3. CH 3CH 2CH 2CH 2OH
is 4.
1. 10  2 0  30 2. 10  2 0  30
CH 3 CH CH 2CH 3
0 0
3. 1  2  3 0 0 0
4. 1  2  3 0
146. Which of the following Order regarding acidity OH

of the following compounds is correct ? 151. The order of reactivity of alcohols towards
hydrogen halide is
1. ROH  HC  CH  NH 3 1. benzyl  30  20  10
2. benzyl  30  20  10
2. ROH  HC  CH  NH 3
3. 30  20  10  benzyl
3. ROH  HC  CH  NH 3 4. 30  20  benzyl  10
4. ROH  HC  CH  NH 3
152. The dehydration of 1-butanol gives 159. Which of the following compounds on reaction
1. 1-butene as the main product with CH3 Mg Br Will give a teritiary alcohol?
2. 2-butene as the main product 1) C2H5 CHO 2) C2H5 COOCH3
3. equal amounts of 1-butene and 2-butene
4. 2- methylpropene 3) C2H5 COOH 4)
153. The relative order of basicity of conjugate bases
is 160. The alcohol which gives the most stable
1. OH   OR   HC  C  carbonium ion on dehydration is:
2. OH   HC  C   OR  1) (CH3)2 CHCH2OH 2) (CH3)3 C - OH
3. HC  C   OH   OR  3) CH3 CH2CH2 CH2 OH 4) CH3-CH-CH2CH3
161. 0.037g of an alcohol R-OH was added to CH3MgBr
4. HC  C   OR   OH  and the gas evolved measured 11.2ml at STP.The
154. A mixture of methanol vapour and air is passed molecular mass of R--OH will be
over heated copper. The products are 1) 47 2) 79 3) 74 4) 77
162. Which of the following reactions will yield
1. CO  H 2O 2. HCHO  H 2
propan-2-ol?
3. HCOOH 4. CO  H 2O H 
1) CH 2  CH  CH 3  HOH 
155. An alcohol on axidation gives CH 3COOH CH MgBr / HOH
2) CH 3  CHO 
3
and CH 3CH 2COOH . The alcohol is C H MgI / HOH

2 5
3) CH 2 O 
1. CH 3CH 2OH
Neutral k Mno4
4) CH 2  CH  CH 3  
2. CH 3CH  OH  CH 2CH 3 163. Ethanol is dehydrated as,
3.  CH 3 2 C  OH  CH 2 CH 3
4. CH 3CH  OH  CH 2CH 2CH 3

156. In the esterification reaction, the correct order
of reactivity of alcohols is
1. CH 3OH  CH 3CH 2OH   CH 3  CHOH
2. CH 3OH   CH 3  CHOH  CH 3CH 2OH Major products (A),(B) and (C) are respectively
:
3. CH 3CH 2OH   CH 3  CHOH  CH 3OH (A) (B) (C)
1) C2H5HSO4 C2H5OC2H5 C2H4
4.  CH 3 2 CHOH  CH 3OH 2OH  CH 3OH 2) C2H4 C2H5OC2H5 C2H5HSO4
LEVEL-V 3) C2H5HSO4 C2H4 C2H5OC2H5
4) C2H4 C2H5HSO4 C2H5OC2H5
157. An alcohol (A) on heating with concentarated 164. If ethanol dissolves in water, water,then which
H2 SO4 gives alkene (B) can show the of the following would be happened?
1) Absorption of heat and decrease in volume
geometrical isomerism. The compound(A) is:
2) Emission of heat and decrease in volume
1) (CH3)2 C (OH) CH (CH3)2 3) Absorption of heat and in crease in volume
2) (CH3)2 C (OH) CH2 Me 4) Emission of heat and in crease in volume
3) CH3 CH2 CH (OH) CH3 165. Which of the following ‘gem’ diols in stable?
4) All of the above OH OH
158. Teritary alcohol is obtained as major product in  
1) CH 3  C  H 2) CBr3  C  H
1) (CH3)2CH-CH=CH2 oxymercura
tion / demercurat
 ion
  OH OH
2) (CH3)3C-CH=CH2 dil
H 2 SO4
 OH

OH

3) (CH3)2CH-CH=CH2 Hydroboration ,Oxidation
     3) CF3  C  H 4) C6 H 5  C  C6 H 5
OH OH
4) All of the above
166. Final product (D) in the seguence of reaction is 1) CH3OH 2) CH3COCH3
3) CH3CHO 4) CH3 CHOHCH3
172. An compound (X) with molecular formula C3H8O
caon be oxidised to (Y) With a molecular formula
C3H6O2 (X) with molecular formula C3H8O can be
oxidised to (y) with a molecular formula C3 H6O2.(X)
1) CH3 CH(CH3)OH 2) (CH3)2 CH OH is most likely:
3) (CH3)2 CH CH2 CH2OH 1) Primary alcohol 2) Secondary alcohol
4) (CH3)2 CHO CH2CH3 3) aldehyde 4) Ketone
167. Which of the following alcohols will dehydrate 173. Reaction, (CO+H2)+H2 673 k ,300 atm ,/ Cr2O3  zno
most rapidly when treated with Con c.H2SO4? 
may by used for manufacture of :
1) CH3 CH(OH)C(CH3)3
1) HCHO 2) CH3COOH
2) CH3 C(CH3)(OH)CH( CH3)2
3) HCOOH 4) CH3OH
3) (CH3)2 CH CH (OH) CH3
174. An organic compound gives hydrogen on reacting
4) CH3 CH2 CH2 CH2 OH
with sodium metal.It also gives iodoform test and
168. In the reaction,
forms an aldehyde of molecular formula C2H4O
CH3 C(CH3)2 CH2OH Conc . H 2 So 4 the on oxidation with acidified dichromate the
Product (S) Obtained will be: compound is
1) CH3OH 2) CH3COOH
1) CH2 CCH2 CH3 3) CH3CHO 4) C2H5OH

CH3
175. In reaction sequence,
2) CH 3  C  CH  CH 3 HOCl R
CH 2 OH
H 2C  CH 2   M   |
| CH 2 OH
CH 3 Molecule M and reqgent ‘R’ respectively are:

1) CH3CH2 and NaOH 2) CH3CH2OH and H2So4
3) 3) CH2Cl- CH2OH and aq.NaHCo3
CH3  C  CH  CH2 4) CH3- CH3 and heat

CH3 176 Match the following
4) This alcohol cannot be dehydrated List-I List-II
169. Lucas test of alcohols involves following reation
a) Wood alcohol p) CH 3OH
Anhydrous Zncl2
R-OH+ HCl   RCl  H 2O b)Grain alcohol q) C2 H 5 OH
Conc c) Rectified spirit r) Petrol
Select the correct statements for the Lucs test contains
d) Power alcohol s) 4.13% water.
1) ROH behaves as a base. contains
2) Lesser is the acidic character of 1. (a-p) (b-q) (c-q,s) (d-q,s)
alcohol,greater is its reactivity towards Lucas 2. (a-q) (b-p) (c-r) (d-s)
reagent. 3. (a-s) (b-s) (c-q) (d-p)
3) Reactivity of 10,20 ,30 alcohol, lies in the 4. (a-r) (b-s) (c-p) (d-q,p)
following sequence ( for Lucas reaction)
30 > 20>I0 COMPREHENSION TYPE QUESTION
4) CH3OH gives Lucas test most quickly
170. An organic compound ‘A’ Containing C,H and O The mother liquor left after crystallization of cane
has a Pleasant odour with boiling point 780 on sugar is called molasses. Molasses contain
boiling ‘A’ with Conc H2SO4,a colourless gas is sucrose upto 30.40%.Molasses is diluted to 10%
and alkaline k Mno4.The organic liquid ‘A’ is:
1) C2H5 Cl 2) C2H5 COOCH3 solution and acidified with H 2 SO4 antil pH is equal
3) C2H5OH 4) C2H6 to 4.The above solution is transferred into
171. An organic compound ‘X’ on treatment with fermentation tank after adding yeast and required
acidified k2Cr2 O7 gives a Compound ‘y’ Which amounts of ammonium Sulphate and ammonium
reacts with I 2 and Na 2Co 3 to f orm tri- phosphate salts are added as food for yeast.The
iodomethane.The compound ‘x’ is:
0
solution is kept for 2-3 days at 30 C . Yeast secrete 131) 1 132) 1 133) 1 134) 2 135) 4
invertase and zymase and fermenatation takes 136) 1 137) 2 138) 4 139) 1 140) 3
place with these enzymes. Invertase converts 141) 4 142.1 143.2 144.1 145.4
sucrose intoglucose and fructose while Zymase 146.1 147.2 148.4 149.1 150.2
converts these products into ethyl alcohol liberating 151.1 152.2 153.1 154.2 155.2
156.1 157. 3 158. 2 159. 4 160. 2
CO2 as by product Alcohol obtained in the process
161. 3 162. 1 163. 1 164. 3 165. 3
is called WASH or WORT (6-10%) WASH is 166. 3 167. 3 168. 1,2 169. 1,2,3170. 3
converted into 93-95% alcohol or RECTIFIED 171. 4 172.1 173. 4 174.4 175.3
SPIRIT by fractional distillation. And then into 100% 176. 1 177. 1 178.1 179.1
alcohol or absolute alcohol by distilling rectified
spirit with CaO and then calcium gives absolute HINTS
alcohol. Generally 95% aqueous ethylalcohol is
known as rectified spirit.
177. The two enzymes present in yeast that are 1.
responsible for the formation of ethylalcohol from
molasses in the fermentation process are
1) Invertase, zymase 2.  CH 3 3 C  OH
2) Invertase, diastase
3) Zymase, diastase 3.  CH 3 3 C  OH
4) Invertase, maltase
178. During the fermentation of molasses the optimum
pH maintained is
1) 4 2) 2 3) 7 4) 10 4. is glycerol
179. The amount of water present in rectified siprit is
1) 4.4 % 2) 10% 3) 95% 4) 80%
5. 1- Butanol, 2-methyl-1-propanol both chain
isomers.
KEY
6. Mannitol is Hexahydric
1) 2 2) 4 3) 4 4) 3 5) 4
6) 1 7) 2 8) 4 9) 1 10) 1 7. HO  CH 2  CH  OH   CH 2  OH is
11) 2 12) 1 13) 2 14) 3 15) 4
16) 4 17) 2 18) 3 19) 4 20) 1 glycerol.
21) 3 22) 1 23) 3 24) 3 25) 2 8. Alcohols and ethers are functional isomers when
26) 2 27) 2 28) 3 29) 2 30) 3 MF is same
31) 3 32) 1 33) 1 34) 1 35) 1 11. Ethyl alcohol is a constituent in wine
36) 1 37) 3 38) 3 39) 3 40) 4
41) 4 42) 4 43) 1 44) 1 45) 3 13. CH 3  CH  OH   CH 2  CH 3
46) 2 47) 4 48) 1 49) 3 50) 3
51) 2 52) 2 53) 1 54) 1 55) 3 14. HO  CH 2  CH  OH   CH 2  OH is
56) 4 57) 3 58) 4 59) 4 60) 4
61) 4 62)1 63) 4 64) 1 65) 4 glycerol.
66) 1 67) 3 68) 2 69) 2 70) 2 15. Mannitol is Hexahydric
71) 2 72) 3 73) 2 74) 4 75) 4
76) 1 77) 4 78) 4 79) 1 80) 1 19. CH 3  CH 2  CH 2  CH 2  OH and
81) 3 82) 1 83) 1 84) 2 85) 1
86) 3 87) 1 88) 2 89) 1 90) 4 CH 3  CH  OH   CH 2  CH 3 and
91) 3 92) 1 93) 4 94) 4 95) 4
96) 1 97) 2 98) 4 99) 2 100) 3  CH3 2 CH  CH 2  OH and
101) 4 102) 2 103) 3 104) 1 105) 1
106) 1 107) 1 108) 4 109) 3 110) 4  CH 3 3 C  OH
111) 3 112) 4 113) 3 114) 1 115) 3
Zymase
116) 3 117) 4 118) 2 119) 1 120) 2 20. Glu cos e   ethyl alcohol
121) 3 122) 2 123) 1 124) 3 125) 2 21. Lucas reagent is a mixtere of
126) 3 127) 3 128) 4 129) 3 130) 2
64.
Conc.HCl  anhy ZnCl2

22. Alkyl halides on hydrolysis gives alcohols H
CH 3CH 2OH  CH 3COOH  
Maltase
23. Maltose   glu cos e CH 3COOC2 H 5  H 2O
24. CaO  Ca
Rectified spirit  66. Inter molecualr Hydrogen bonding
 abbolute alcohol.
diastage
25. Starch  67. Acidified K 2 Cr2 O7 an oxidiant
Maltose

diastage H
27. Starch  maltose 68. ROH  RCOOH   RCOOR  H 2O
28. Ethyl alcohol is used as antigreeze for automobile
rediators 69. C2 H 5OH  HI  C2 H 5 I  H 2 O
33. Yeast can produce enzymes at P H  4 72. C2 H 5OH is 10 - alcohol
34. Rectified spirit is 93 - 95% ethyl alcohol
73. n - propyl alcohol doesnot cortain CH 3CO group
35. C2 H 5OH  HBr  C2 H 5 Br  H 2O
37. It is an industrial method of preparation of ethyl
76. A  C2 H 5ONO2 (ester of alid)
alcohol.
77. With PCl5 , ‘C- O’ bond clearage takes place
Zymase
38. glu cos e  ethyl alcohol 79. Inter molcular hydrogen bonding
Zno  cr2O3 81.
40. CO  H 2   CH 3OH
41. Potatoes, maizes , molasses contains C2 H 5OH  H 2 SO4 
 H2O

saccharides H 2O
C2 H 5 HSO4   C2 H 4  H 2 SO4
42. C6 H12O6  2C2 H 5OH  2CO2 Cu
82. CH 3CH 2OH 
3000 C
 CH 3CHO  H 2
Zno  cr2O3
46. CO  H 2 
 CH 3OH
83. Preparation method of CHCl3 from C2 H 5OH
48. X=3
and moist bleaching power (Refer Ist preparation)
49.
Cu
H 2O 84. CH 3CH 2OH 
3000 C
 CH 3CHO  H 2
H C H O  R  M g X  
 H
LiAlH 4
R  C H 2  O H  M g X O H  85. CH 3COOH   C2 H 5OH
86. Tertiary alcohols react immealictely with Lucas
52. 95.5%C2 H 5OH  4.4% H 2O iis called reagent
Azeotraopic mixtures Conc .H 2 SO4 /170 C 0
87. C2 H 5OH   C2 H 4
53.
H 2O 88. 3C2 H 5OH  PCl3  3C2 H 5Cl  H 3 PO3
HCHO  R  MgX 
H

R  CH 2  OH  MgX  OH  89. 3C2 H 5OH  PCl3  3C2 H 5Cl  H 3 PO3
0
Conc . H 2 SO4 /170 C
H 2O
57. CH3 MgI  CH3COCH3   CH3 3 COH C2 H 5OH   C2 H 4  H 2O
H 90. ( or )
Al2O3 / 3500 C
58. Ethanol and Methanol form hydrogen bond
91.
with water

C 2 H 5 O H  CH 3 CO O H  H
59. Conc.H 2 So4 and Al2 O3 are dehydrating
C H 3C O O C 2 H 5  H 2 O
agerts
Conc . H 2 SO4 0
92. R  OH  HCl    R  Cl  H 2O 113. CU / 300 C
C2 H 5OH   CH 3CHO  H 2
93.
Al2O3
C2 H 5OH   C2 H 4 114. Ethylalcohol has active hydrogen attached to
3600 C
oxygen.
94. -OH bond fission takes place with sodium 115. Four moles of blaching power needed in the
prepration of one mole of chloroform
95. 2C2 H 5OH  2 Na  2C2 H 5ONa  H 2 116
96. 3C2 H 5OH  PCl

Cl2 3
 2C2 H 5Cl  H 3 PCl3 PCl3
CH 3OH   CH 3Cl
C2 H 5OH 
2 HCl
 CH 3CHO  A
97. 3Cl2 KCN H2O
C2 H 5OH  CCl3CHO
3 HCl 
 CH 3CN   CH 3COOH
 B C 
98. All primary alcohols produce same amount of H2
gas with sodium metal. 117. C2 H 4 decolourises bromine water and
99. alkaline KMnO4
100. Order of reactivity of alcohols to wards Lucas 118. 20  or  30 alcohols on oxidation give ketone
reagent is 30  20  10
119.
101. PCl3 acts as only a halogenating agent
120. Addition reactions of C2 H 5OH
102. 121. 20  or  30 alcohols on oxidation give ketone

122. A  C2 H 4 B  C2 H 5Cl
103.
123. A  C2 H 5OH B  C2 H 5 Br C  C2 H 4
104. Ethanal is a associated liquid through hydrogen 124.
bond. due to the formation of
A  CH 3OH , B  CH 3ONa, C  CH 3Cl
105. CaCl2 3C2 H 5OH
125. X  C H 3  C H 2  C H 2  O H C 3 H 8O 
106. Ethyl alcohol is soluble in polar and non polar
solvents. Y  CH 3  CH 2  COOH  C3 H 6O2 
Conc.H2SO4
107. 2C2H5OH 
1400 C
 C2H5OC2H5  H2O 126. X  C2 H 5OH Y  C2 H 4
Conc.H2SO4 127. C2 H 5OH  4 I 2  CI 3CHO  5HI
2C2 H5OH 
1700 C
 C2H4  H2O
4 n P  O3  2 KI  H 2 O  2 KOH  I 2  O2
108. C2 H 5OH  Br2   C2 H 5 Br  HBr
109. 2- hydroxy- 2 - methyl propane is a tertiary alcohol
128. CH 3CO group is present
C 2 H 5 O H  K
M nO 4 / H 
129. A  CH 3  CH 2  CH 2  Cl

O
 C H 2 C O O H
110.
 C
2 H 5 O H / H 2 SO 4
    C H 3C O O C 2 H 5 B  CH 3 CH  CH 2
C 2H  H 2 S O 4  8
0
0 C
 C2H 5HSO4
A to B dehdrohalogenation
4
111. H 2O /  130. x= secondary alcohol ; y= ketone
   C 2 H 5 O H  H 2 S O 4
131. M.W= 46, Ethyl alcohol gives iodoform test
112. C2 H 5OH  SOCl2  C2 H 5Cl  HCl  SO2
132. X= RCH 2OH ;Y= R2CHOH
133. A  CH 3COOH , B  C2 H 5OH  

CH 3CH  OH  CH 2 CH 2CH 3 
O
155.
134. A   CH 3  2 CHOH , B   CH 3 3 COH CH 3COOH  CH 3CH 2COOH
138. Alcohols are converted into halo alkane with 156. Correct order or reactivity is
Phophorous trihalides CH 3OH  CH 3CH 2OH   CH 3 2 CHOH
140. A  C2 H 5Cl , B  C2 H 5ONO
157 A  CH 3CH 2CH  OH  CH 3
141. 3C2 H 5OH  PBr3  3C2 H 5 Br  H 3 PO3 B  CH 3CH  CHCH 3
142 The reactivity of alcohols with active metalsis
dil . H SO
30  20  10  CH 3 3  C  CH  CH 2  2
 4
158.
i, Hg  OAC  / THF  H O
2  CH 3 2 C  OH   C2 H 5
143. CH3CH  CH2  
2
ii , NaBH4 ,OH 
159.
CH 3 CH
|
CH 3
OH
BH inTHF
144. 3CH 3CH  CH 2  3
  CH 3CH 2CH 2 3 B
3 H 2 O2
OH 
 CH 3 CH 2 CH 2 OH  H 3 BO3
145. The correct decreasing order of dehydration of
the given alcohols with acis like conc.
H 2 SO4 is 30  20  10 160. 30 carbonium ion more stable
146. The correct order of acidity is
161. 11.2 ml of CH 4 at STP is formed by 0.037 g
ROH>HC  CH> NH 3
of R-OH
O 
147. CH 3 CH
|
CH
|
CH 2 CH 3  HIO
4  22.400 ml CH 4 at STP .......?
OH OH
0.037  22, 400
CH 3CHO  CH 3CH 2CHO =
148. The number of c-c bond broken is equal to the
11.2
= 74g
number of HIO4 molecules used.
162. Conceputal
149. Catalytic reduction of ‘CO’ in presence of
163. A  C2 H 5 HSO4
' Zno  Cr2 O3 ' constitutes industrial method of
preparation of methanol. B  C2 H 5OC2 H 5
150. 30 carbanium ion is most stable. C  C2 H 4
151. The order of reactivity of HX with ROH is
164. H  Ve, v  Ve
benzyl > 30  20  10
152. The reaction occur with rearrangement as OH
|
2 carbocation is more stable than 1
0 0 carbo
165. CF3  C|  H is stabilised by intermolecular
cation. OH
153. The relative order of basicity of conjugate base
hydrogen bonding.
is opposite to that of acid.
CU 166. D   CH 3  2  CH  CH 2  CH 2OH
154. CH 3OH 
air
HCHO  H 2
167. Due to steric factors.
168. C2 H11OH can have four primary alcohol
isomers
CH 2  CH  CH 2  CH 3
169. | and
CH3
CH 3  C  CH  CH 3
|
CH 3
170. Primary alcohol does not give turbidity
immediately with Lucas reagent.
171. A  C2 H 5OH , B.P  780 C
  O
CH 3CHOHCH 3  CH 3  CO  CH 3
172. I 2 / Na2CO3
  CHI 3
173. A perimary alcohol on oxidation form
carboxylic acid with same no of carbon atoms.
673 K ,300 atm
174.  CO  H 2   H 2 
Cr O  Zno
2 3
 CH 3OH
175. C2 H 5OH gives hydrogen gas with sodium

metal and under go idoform test.
CH 2  Cl
176. M  |
CH 2  OH
R = aQ. NaHCO3
PHENOLS
PHENOLS, NOMENCLATURE
AND PREPARATION
METHODS OF PHENOLS Hydroquinone (or)quinol Benzene-1,4-diol
SYNOPSIS
NAMING OF PHENOLS
Molecule Common name IUPAC name
2,6-dimethyl phenol
Phenol Phenol
METHODS OF PREPARATION OF PHENOL

:
1) Phenol was first isolated from coaltar.
O-cresol 2-methyl phenol 2) From haloarenes
350o C & 300 atm

+ NaOH  
m-cresol 3-methyl phenol
HCl


3) From diazonium salt :

p-cresol 4-methyl phenol
05o C
 NaNO2  HCl 
Catechol Benzene-1,2-diol
H O, warm  N 2  HCl
2  

4) From benzene sulphonic acid :

Resorcinol Benzene-1,3-diol
conc.H SO ,SO
  2 
4
3 

phenol. The hydroxyl group in phenol is directly
attached to sp 2 carbon of benzene ring. The sp 2
molten NaOH HCl
   
 
 carbon attached to ‘O’ being more electronegative
than sp3 carbon of alcohols, it decreases the electron
density on oxygen. Because of this oxygen develops
+ NaCl still more electron seeking character and releases
proton by taking the shared pair of electrons with it.
5) From cumene : Phenol is manufactured from The acidic nature of phenol can also be explained
cumene (isopropyl benzene) .On the basis of resonance stabilization of phonoxide
ion.
Electron withdrawing groups of phenol increase the
acidic nature.
O (oxidation with air)
2      Electron releasing group of phenol decrease the acidity
of phenols.
Acidic strength increases with the decrease of the
P K a values.
The order of the strength of phenols is as follows
H / H O
2
  
cumene hydroperoxide  CH 3COCH 3 >

ACIDITY OF PHENOLS : The reactions of
phenol with metals as well as NaOH indicate it is
relatively more acidic than alcohols and also water.
This is explained on the basis of the structure of
The greater the pKa value, the weaker the acid.
pKa Values of some Phenols and Ethanol
Compound Formula pKa

o - Nitrophenol o  O2 N  C6 H 4  OH 7.2
m - Nitrophenol m  O2 N  C6 H 4  OH 8.3
p - Nitrophenol p  O2 N  C6 H 4  OH 7.1
Phenol C6 H 5  OH 10.0
o -Cresol o  CH 3  C6 H 4  OH 10.2
m -Cresol m  CH 3C6 H 4  OH 10.1
p -Cresol p  CH 3  C6 H 4  OH 10.2
Ethanol C2 H 5OH 15.9
polar nature of O-H group. Electron releasing groups
like alkyl groups increase the electron density on
oxygen and decrease the polarity of O-H bond. This
decreases the acidic strength.
> > > The order of acidic strength is
H 2O  RCH 2OH  R 2CHOH  R 3COH
Even through the electron releasing groups
like  CH 3 , C 2 H 5 etc decrease the acidic strength
of phenol, Phenol does not liberate CO2 with
Na 2CO 3 or NaHCO 3 because phenol is weaker
> > > = acidic than carbonic acid and carboxylic acids.
ESTERIFICATION OF PHENOL :
Phenols react with carboxylic acids and their
derivatives like acid chlorides and anhydrides to form
esters. This reaction (benzoylation ) is called
Schotten-Baumann reaction.
C 6 H 5OH  RCOOH
 C 6 H 5  O  CO  R  H 2O
pyridine
C6H5OH RCOCl C6H5  OCO R  HCl
PHYSICAL AND CHEMICAL PROPERTIES
OF PHENOLS Salicylic acid on acetylation gives acetyl
PHYSICAL : 1) Phenol has higher boiling point than salicylic acid known as Aspirin.
the arenes or haloarenes or ethers of same molecular
weight. It is due to the formation of intermolecular
hydrogen bond. ) 2 conc
 (CH 3CO O
 
. H 2SO 4

2) Phenols are relatively more soluble in water due
to their ability to form hydrogen bonding with water.
3) As the hydrocarbon part increases in size and mass,
the solubility decreases.
Electrophilic aromatic substitution reactions of phenol
In phenol, -OH group is ring activating and
1) Acidic nature of phenol :
ortho and para directing as these positions get more
Alcohols and phenols react with active metals
electron density through resonance structures.
like Na, K, Al etc to liberate hydrogen gas.
a) NITRATION :
2ROH  2 Na  2RONa  H 2
C 6H 5OH  2 Na  2C 6 H 5ONa  H 2
Phenols also react with aqueous NaOH
solution to produce the salt sodium phenoxide and
water.
dil . HNO
  3  +
C 6H 5OH  NaOH  C 6 H 5ONa  H 2O
The acidic nature of alcohols is due to the
The ortho and para isomers can be separated
by steam distillation.
O-nitrophenol is steam volatile due to
intramolecular hydrogen bond.
H 2O
P-nitro phenol is less volat ile due 3Br2 
0  50 C

intermolecular hydrogen bond.
Phenol when treated with conc. HNO3 gives
2,4,6-trinitrophenol known as picric acid
c) REIMER-TIEMANN REACTION :
Phenol when treated with chloroform in the
presence of NaOH give salicylaldehyde.
Mechanism :
conc .HNO
  3  i) C H C l  O H  H O  C C l  : C C l  C l
3

2

3 2

Dichloro carbene ( : CCl2 ) is the attacking

electrophile in this reaction :
The yield of the reaction product is poor. ii) + : CCl2 

Now a days picric acid is prepared by treating phenol
with conc. H 2SO 4 and then with conc. HNO3 .

conc.H SO
2 4 conc
.HNO
 
3

 NaOH
OH
CHO
b) HALOGENATION :
H+
Salicylaldehyde
d) KOLBE’S REACTION :
Br2 in CS2 at 0o C +

 Phenoxide ion generated by treating phenol with
sodium hydroxide is even more reactive than phenol
towards electrophilic aromatic substitution.
When the reaction is carried out in solvents of low
polarity such as CHCl 3 or CS2 and at low
temperature, monobromophenols are formed. NaOH i ) CO & ii ) H 
Here no Lewis acids like FeBr3 are required because    2  
highly activating effect of -OH group polarises
bromine quickly.
Phenol reacts with bromine water and gives 2,4,6-
tribromo phenol (white precipitate)
3) It is used as a preservative for ink.
4) It is used in the manufacture of drugs like
Aspirin, Salol etc.
5) It is used for causterising wounds caused by
the bite of mad dogs.
TESTS OF PHENOL :
i) Aqueous solution of phenol gives violet colour
with a drop a FeCl3 .
e) ACTION OF ZINC DUST : Phenol on heating ii) Aqueous phenol gives white precipitate with
with zinc dust produces benzene. bromine water.
OH
iii) Phenol gives blue colour with ammonia and
+ Zn + Zno
sodium hypochlorite.
f) OXIDATION : Phenol oxidation with chromic LEVEL - I
MODEL QUESTIONS
acid ( Na 2Cr2O 7  H 2SO 4 ) produces NOMECLATURE AND PREPARATION
benzoquinone, which is a conjugate diketone. In MEHODS OF PHENOLS
the presence of air, phenols are slowly oxidised to 1. Phenol is also called
dark coloured mixtures containing quinones. 1. salicylic acid 2. benzyl alcohol
3. carbolic acid 4. salol
2. Benzene diazonium chloride on hydrolysis
 c
h r o m ic a c id
 
H 2C rO 4
 gives
1. Benzene 2. Benzyl alcohol
g) FRIES REARRANGEMENT : 3. Phenol 4. Chlorobenzene
3. When phenol is treated with excess of bromine
water, it gives
anhydrous AlCl
 (CH 3CO) 2 O    3  1. m-bromophenol
2. o- and p-bromophenol
3. 2,4-dibromophenol
4. 2,4,6-tribromophenol
4. Phenols do not react with
1. sodium bicarbonate
AlCl3
2. sodium hydroxide
Re

arrangement
 +
3. potassium hydroxide
4. ferric chloride
i ) CHCl / NaOH
3 
  
5. Phenol ii ) H 
Salicyladehyde. This
USES OF PHENOL :
1) It is raw material for the manufacture of reaction is known as
importantdyes, drugs, pharmaceuticals, 1. Gattermann aldehyde synthesis
polymers and several other compounds. 2. Sandmeyer’s reaction
2) It is strong antiseptic. 2,4-dichloro-3,5 3. Perkin’s reaction
dimethyl phenol is used as powerful antiseptic 4. Reimer-Tiemann reaction
under the name Dettol.
6 Phenol is LEVEL - II
1. a base weaker than ammonia (MODEL QUESTIONS)
2. an acid stronger than carbonic acid NOMECLATURE AND PREPARATION
3. an acid weaker than carbonic acid MEHODS OF PHENOLS
4. a neutral compound 14 C 6H 5OH  CHCl 3  NaOH 
7. Which does not have a carboxyl group ?
salicylaldehyde
1. Picric acid 2. Ethanoic acid
The electrophile involved in the above reaction
3. Aspirin 4. Benzoic acid
is.
8. Picric acid is a yellow coloured compound.

Its chemical name is 1. dichloromethyl cation (C HCl )
1. m-nitrobenzoic acid 2
2.2,4,6-trinitrophenol 2. dichlorocarbene (: CCl 2 )

3. trinitrotoluene 3. trichloromethyl anion (CCl3 )
4. trinitroaniline
9. Phenol reacts with bromine in carbon 
4. formyl cation (C HO)
disulphide at low temperature to give
1. m-bromophenol
2. o- and p-bromophenol 15. Which of the following is most volatile ?
3. p-bromophenol 1. p-nitrophenol 2. m-nitrophenol
4. 2,4,6-tribromophenol 3. o-nitrophenol 4. all of these
10. Phenols is less acidic than 16. The most acidic compound among the
1. p-nitrophenol 2. ethanol following is
3. cresol 4. benzyl alcohol
1 phenol 2. ethanol
PRACTICE QUESTIONS
3. 3,5-dinitrophenol
11. Phenol on treatment with conc. HNO3 gives
4. 4-methoxy phenol
1. picric acid 17. Which one of the following compounds would
2. o-and m-nitrophenols
undergo nitration with greatest ease
3. o- and m- nitrophenols
4. none of the above 1. benzene 2. phenol
i) O
3. nitrobenzene 4. benzoic acid
 2
12. Cumene ii ) H 2O 2 H 
(X) and (Y) LEVEL - III
(X) and (Y) respectively are MODEL QUESTIONS
1. toluene, propene 18. In the following compounds
2. toluene, propylchloride I. Phenol II. 4-methyl phenol
3. phenol, acetone III. 3-nitrophenol IV. 4-nitrophenol
4. phenol, acetaldehyde The order of acidity is
13. In the reaction C 6H 5 NH 2 1. III > IV > I > II 2. I > IV > III > II
NaNO  HCl, O C H 2O, warm
o 3. II > I > III > IV 4. IV > III > I > II
 2   X     Y ;
19. The correct acidic order of the following is
Y is
I. Phenol II. 4-methylphenol
1. C 6H 5Cl 2. C6 H 6 III. 4-nitrophenol
3. C 6H 5OH 4. C 6 H 5CHO 1. I > II > III 2. III > I > II
3. II > III > I 4. I > III > II
Assertion, Reason Type Questions : 28. Phenol can be prepared by
1. Dow process 2. claisen reaction
3. Reimer-Tiemann reaction
Use the following key to choose the correct
4. Cannizzaro reaction
answer. 29. The treatment of phenol with phthalic anhydride
1) Both A & R are correct, R is the correct in the presence of cencentrated sulphuric acid
explanation of A. produces
1. methyl orange 2. phenolphthalein
2) Both A & R are correct, R is not the 3. methyl red 4. Thymol blue
correct explanation of A 30. Which of the following orders is true regarding
3) A is correct but R is incorrect the acidic nature of phenol
4) A is incorrect but R is correct 1. phenol > 0-cresol > o-nitroo phenol
2. phenol < 0-cresol < o-nitroo phenol
20. Assertion (A) : Phenol is more reactive than 3. phenol > 0-cresol < o-nitroo phenol
benzene towards electrophilic reactions. 4. phenol < 0-cresol > o-nitroo phenol
Reason (R) : The +R effect of OH group 31. Which of the following statement si not true
1. phenol is soluble in NaOH
increases the electron density on benzene 2. phenol is a weak acid
nucleus. 3. phenol gives violet colouration with neutral
21. Assertion(A) : p-Nitrophenol is stronger acid
FeCl3
than o-nitrophenol.
Reason (R) : Intramolecular hydrogen 4. phenol liberates CO2 from Na2 CO3
bonding makes ortho-isomer weaker acid than solution
para-isomer. 32. Which of the following orders regarding the acid
22. Assertion ( A) : Phenols are more acidic than strength of phenols is correct
1. p-nitrophenol > p-amino phenol > p-chloro
aliphatic alcohols.
phenol
Reason (R) : Phenoxides are stabilized by 2. p-amino phenol > p-nitro phenol > p-chloro
resonance. phenol
PRACTICE QUESTIONS 3. p-amino phenol > p-chloro phenol > p-nitro
23. Phenol (1 mole) reacts with bromine to give phenol
s-tribromophenol. The amount of bromine 4. p-amino phenol < p-chloro phenol < p-nitro
phenol
required is
1. 3.0 moles 2. 1.5 moles 33. Phenol on treating with concetnrated H 2 SO4
3. 4.5 moles 4. 6.0 moles at 15  20 0 C mainly produces
24. The most acidic compound among the 1. phenol-2,4,6-tri sulphonic acid
following is 2. phenol -2- sulphonic acid
1 phenol 2. ethanol 3. phenol-4-sulphonic acid
3. 3,5-dinitrophenol 4.4-methoxy phenol 4. a 50% mixture of ortho and para phenol
sulphonic acid
25. Which one of the following compounds would 34. Which of the following statements is not true
undergo nitration with greatest ease 1. 0-nitrophenol has a lower boiling point as
1. benzene 2. phenol compared to that of p-nitro phenol
3. nitrobenzene 4. benzoic acid 2. when vapours of phenol are passed over ‘Zn’
LEVEL-IV dust, benzene is formed
26. Phenol on distilling with zinc dust gives 3. The phenolic-OH group is metadirecting
1. benzene 2. diphynyl ether group
3. diphenol 4. zinc phenoxide 4. The phenolic-OH group is ortho and para
27. Salicyclic acid is produced when phenol in directing group
alcholioc KOH is treated with 35. Benzediazonium chloride on reacting with
phenol in weakly basic medium gives
1. CH 3Cl 2. CHCl3 1. benzene 2. chlorobenzene
3. diphenyl ether
3. CH 2Cl2 4. CCl4 4. p-hydroxy azobenzene
36. The reaction 43. Which order is coorect about auidity
OH 1. CH 3 C O O H  C 6 H 5 C O O H  C 6 H 5 O H
OCOC6 H 5
2. C6 H 5COOH  CH 3COOH  C6 H 5OH
ClCOC6 H 5 
3. C6 H 5OH  C6 H 5COOH  CH 3COOH
is known as
1. Wurtz reaction 2. Kolbe reaction 4. C6 H 5OH  CH 3COOH  C6 H 5COOH
3. Rimer-Tiemann reaction 44. When phenol reacts with chloroform and an
4. Schotten-Baumann reaction
37. Phenol is alkali, the compounds formed is
1. a neutral compound salicylaldehyde. If pyrene is used in place of
2. a base weaker than ammonia chloroform, the product obtained is
3. an acid stronger than carbonic acid
4. an acid weaker than carbonic acid 1. Salicylic acid 2. Salicylaldehyde
Phenol  Zn conc.HNO3

 A  Zn
 B  C 3. Phendphthalein 4. Cyclo heranol
38. distillation conc.H SO at 600 C NaOH
2 4
45. The most suitable method of separation of
In the above reaction, compoinds (A), (B) and
equal ( 1: 1) mircture of O-and p-nitrophenols is
(C) are
1. Crystallisation 2. Distullation
1. benzene, nitrobenzene and hydrazobenzene
2. benzene, nitrobenzene and aniline 3. Sublimation 3. Chromatography
3. benzene, dinitrobenzene and m- nitroaniline 46. Assertion (A): O-Phenol sulphonic acid on
4. toulene, m-nitrobenzene and m-toulidine heatin at 100 0 C changes to P-phenol
sulphonic acid.
39. Sodium phenoxide when heated with CO2 Reson (R): Sulphonation of phenol is a
under pressure at 1250 C gives reversible process.
1. salol 2. salicylaldehyde 1. If both A and R are correct and R is correct
3. sodium benzoate 4. sodium salcylate explanation of A
40. Salol prepared from 2. If both A and R are correct but R is not the
1. salcylic acid and methyl alcohol correct explanation of A
2. salicylic acid and phenol 3.If A is correct but R is in correct
3. both 1 and 2 4. asprin and phenol 4. If A is in correct but R is correct
41. OH 47. Assertion (A) : Phenol and benzaic acid can be
distinggleished by NaOH.
K 2 S 2 O8
Heat
 Reson (R): Benzoic acid is stranger acid than
phenol
The product formed in the reaction is 1. If both A and R are correct and R is correct
1. hydroquinone 2. diphenyl ether explanation of A
3. benzoquinone 2. If both A and R are correct but R is not the
4. benzene sulphuric acid correct explanation of A
3.If A is correct but R is in correct
LEVEL-V 4. If A is in correct but R is correct
48. Asseriton (A): Pheyol is more reactive than
benzene towards electrophilic substitution.
42. In the fololwing compounds Reson (R): In the case of Phenol, the
intermediate Carbocation is more resonance
stabilized.
1. If both A and R are correct and R is correct
explanation of A
2. If both A and R are correct but R is not the
correct explanation of A
1. I > IV > III > II 2. II > IV > I > II 3.If A is correct but R is in correct
3. II > I > III > IV 3. IV > III > I > II 4. If A is in correct but R is correct
49. Assertion (A): P-Nitrophenol is strongers acid 1. (1-a-p) (2-a-q) (3-b-s) (4-d-s)
than O-nitrophenol 2. (1-a-p) (2-b-q) (3-c-r) (4-d-s)
Reson (R) Intramolecular hydrogen bonding 3. (1-a-q) (2-b-r) (3-c-q) (4-c-s)
makes ortho - isomer weaker acid than para - 4. (1-b-q) (2-c-r) (3-a-q) (4-d-r)
isomer. COMPREHENSION TYPE QUESTION
1. If both A and R are correct and R is correct The reactions of phenol with metals as well as NaOH
explanation of A
indicate it is relatively more acidic than alcohols and
2. If both A and R are correct but R is not the
correct explanation of A also water. This is explained on the basis of the structure
3.If A is correct but R is in correct of phenol. The hydroxyl group in phenol is directly
4. If A is in correct but R is correct
attached to sp 2 carbon of benzene ring. The sp 2 carbon
50. When phenol is reacted with CHCl3 and
NaOH followed by acidification, salicylaldehyde
is obtained. Which of thefolloiwng species are attached to ‘O’ being more electronegative than sp3
involved in the above mentioned reaction as carbon of alcohols, it decreases the electron density on
intermediates? oxygen. Because of this oxygen develops still more
electron seeking character and releases proton by taking
the shared pair of electrons with it. The acidic nature of
phenol can also be explained .On the basis of resonance
stabilization of phonoxide ion.
Electron withdrawing groups of phenol increase the
acidic nature.
Electron releasing group of phenol decrease the acidity
of phenols.
Acidic strength increases with the decrease of the P Ka
values.
52. Hybridsation of carbon in phenol
1. sp 2. sp 2 3. sp3 4. sp3d
53. Acidity of phenol increase in the presence of
51. Match the following: 1. Electron withdrawing groups
Molecule Common name IUPAC name 2. Electron releasing group
3. both 1, 2
4. Dehydration groups
54. Acidity of strength of phenol increases with
1) a) Phenol p) Phenol
1. increase of P K a value
2. Decrease P K a value
3. does not depond on P K a value
2) b)O-cresol q) 2-methyl phenol
4. increase of p k w value
KEY
1) 3 2) 3 3) 4 4) 2
3) c) m-cresol r)3-methyl phenol 5) 4 6) 3 7) 1 8) 2
9) 2 10) 1 11) 1 12) 3
13) 3 14) 2 15) 3 16) 3
4) d) p-cresol s) 4-methyl phenol

17) 2 18) 4 19) 2 20) 1 CH3
CH3
21) 1 22) 1 23) 1 24) 3 |
|
3 CH
HC OH
25) 2 26. 1 27. 4 28. 1 | 3  COOH
HC
|
29. 2 30. 3 31. 4 32. 4
33. 2 34. 3 35. 4 36. 4 12. O H
CHC
3 OCH3
2
HO
 

37. 4 38. 1 39. 4 40. 2 2
41. 1 42. 4 43. 2 44. 1

X Y
45. 2 46. 2 47. 4 48. 1
49. 1 50. 1,2 51. 2 52. 2 Phenol acetone
53. 1 54.2
 
HINTS NH2 N2 Cl OH
1. Phenol also known as carbolic acid
2 HCl
H2O
13. NaNO

05C
  warm
  N2  HCl
 
2. H 2O + N2 + HCl
C6 H 5 N 2 Cl 
warm
 X Y
(Phenol)
Phenol
OH 14. H 2O  CCl3  : CCl2  Cl 
Br Br electrophile (dichloro carbene)
15. It has intra molecular hydrogen bond
3. + 3Br2 
16,17 If – NO2 is present on the benzene ring of phenols
Br acidic strength increases particularly when that
5. It is Reimer Timann reaction group is at ortho (or) para positions.
6. PKa of phenol = 10 18. Phenol PKa = 10

PKa of carbonic acid is less than 10 4-Methyl phenol PKa = 10.2
3-nitrophenol PKa = 8.3
7. Picric acid 4-nitro phenol PKa = 7.1
8. 2, 4, 6 - trinitro phenol 19. Phenol PKa = 10.0

4-Methyl phenol PKa = 10.2
OH 4-nitrophenol PKa = 7.1
OH
20. –OH group in phenol os ring activating and ortho
Br and para directing as these positions get more
9. Br2 in CS2 +
  electrodensity through resonance structures.
21. If – NO2 is present on the benzene ring of phenols
Br
acidic strength increases particularly when that
Ortho Para group is at ortho (or) para positions.
22. Among alcoholas order of acid strength is tertiary
< secondary < primary
10. PKa of phenol is 10
alcohols are weaker acids than water
11. Picric acid
23. Phenol required 3 moles of benzene
24. If – NO2 is present on the benzene ring of phenols
acidic strength increases particularly when that
group is at ortho (or) para positions.
25. PKa of phenol is 10
Zn
26. C6 H5OH 

C6 H 6  ZnO
27. 39.
40. Solol is obtained form salicyclic acid and phenol
41.
LEVEL-V
42. The correct order of acidity IV > III >  II
29. 43. The correct order of acidity
C6 H 5COOH  CH 3COOH  C6 H 5OH
44.
30. Methyl group is activating group and nitrogroup
is deactivating group.
31. Pehol is a weak acid.
45. O- and P-nitrophenols differ in boiling points.
32. Correct order of acidic strength is P-amino
Phenol < P-chloro phenol < P- nitro phenol 46. During sulphanation of phenol at law
temparature ortho isomer is major products
where as at 100 0 C , it gives mainly para
isomer
33. 47. Both Benzoic acid, phenol react with NaOH
49. P-nitro phenol is more acidic than o-nitro
34. Phenolic - OH group is ortho - and para - phenol
directing 50.
__
OH
C6 H 5 N 2Cl  C6 H 5OH 
35.
C6 H 5  N  N  C6 H 5  OH
37. Phenol is a weaker acid then carbonic acid.
38.
A  C6 H 6 , B  C6 H 5 NO2 , C  Hydrozobenzene
***THE END***
ETHERS  STRUCTURE OF FUNCTIONAL GROUP

SYNOPSIS In ethers, the four electron pairs, i.e, the two bond
NOMENCLATURE : pairs and two lone pairs of electrons on oxygen
 Ethers are the carbon compounds containing are arranged approximately in a tetrahedral
arrangment. The bond angle is slightly greater than
Oxygen atom linked to two alkyl groups.
the tetrahedral angle due to the repulsive
 The general formula of ethers is R  O  R or interaction between the two bulky (-R) groups. The
C-O bond length (141 pm) is almost the same as
 Cn H 2n1 2 O or Cn H 2n 2O in alcohols.
PREPARATION METHODS OF DIETHYL
 The radico -functional names of ethers are derived
ETHER
by listing the two alkyl groups in an alphabetical
order as separate words and then adding the
word ether at the end.
1. FROM ETHYL ALCOHOL: Ethyl alcohol gives
 Ethers are considered to be dialkyl derivativesof
diethyl ether by acid -catalysed condensation
water.
reaction
 They are named in two ways namely
a) common system and b) IUPAC System conc. H 2 SO4
C2 H 5OH  HOC2 H 5   C2 H 5OC2 H 5  H 2O
1400 C
 In common system, ethers are named after alkyl
groups attached to oxygen atom. The catalytic dehydration of ethalnol with
 For simple ethers , the common name is di alkyl
Al2O3 at 250  260 C .
ether.For mixed ethers, the common name is
alkyl, alkyl ether.Ethers are named first in the
Al2 O3
alphabetical order followed by the word ether in 2C2 H 5OH 
2600 C
 C2 H 5OC2 H 5  H 2O
common system.
The formation of ether is a necleophilic bimolecular (SN2)
 In IUPAC system, Ethers are named as alkoxy
involving the attack of alcohol molecule on a protonated
alkanes. The smaller alkyl group along with
Oxygen atom is taken as alkoxy part while the alcohol, as indicated below:
larger alkyl group as alkane part. i) CH3-CH2-O-H + H+  CH3-CH2-O+-H2
Formula Common name IUPAC
ii) CH3CH2-OH + CH3 - CH2 - O+-H2 
name
CH3 CH2 - +OH CH2CH3 + H2O
CH 3OCH 3 dimethyl ether ethoxy
iii) CH3 CH2 - +OH CH2CH3 CH3CH2 - O - CH2CH3+H+
methane
2. WILLIAMSON SYNTHESIS : Ethyl halide
CH 3OC2 H 5 ethylmethylether ethoxy reacts with Sodium or potassium ethoxide to
form diethyl ether the reaction involves SN2 attack
ethane of an alkoxide ion on primary alkyl halide.
C2 H 5OC2 H 5 diethyl ether ethoxy
ethane C 2 H 5 ONa+IC 2 H 5  C 2 H 5OC 2 H 5  NaCI
CH 3OC3 H 7 methyl n-propyl ether ethoxy Alkyl halide is to be primary because with other
alkyl halides alkenes are formed .
propane
C2 H 5OCH  CH 3 2 ethyl isopropyl ether 2-ethoxy
CH 3 Br  NaO  C   CH 3 3
CH 3
propane |
C6 H 5OCH 3 Anisole Anisole  CH 3  O  C  CH 3  NaBr

|
CH 3
 CH 3 3 C  Br  CH 3ONa 
CH 3  C  CH 2  NaBr
|
CH 3
Alkoxides are nucleophiles and strong bases.\ Cl
CH3CH2OCH2CH3   2  
D a rk
OH ONa OR
 1
CH 3 - C H (Cl) - O - C H(Cl) - CH 3
R-X
+ NaOH
(  ,  ' dicholoro diethyl ether)
Cl
Phenols are also converted to ethers by this method. CH3CH2OCH2CH3  2
Sunlight 
3. From ethyl bromide:Ethyl bromide reacts with
dry Silver oxide to from diethyl ether C2Cl5 – O – C2Cl5
(perchloro diethyl
C2 H 5 Br  Ag  O  Ag  Br  C2 H 5  ether)
 ELECTROPHILIC SUBSTITUTION.
C2 H 5OC2 H 5  2 AgBr 1) HALOGENATION:
Phenylalkyl ethers undergo usual halogenation in the
PHYSICAL AND CHEMICAL PROPERTIES : benzene ring. It is due to the activation of benzene ring
 It is a colourless, highly volatite liquid(b.p=307.5 by the methoxy group. Para isomer obtained in 90%
K). It is highly inflammable. yield.
 It has characterstics pleasent odour and produce
temparary unconsciousness when its vapour are
in haled.
 It is slightly soluble in water and readily soluble
in organic solvents. It is lighter than water.
Due to lack of H-bonding, its BP is less than its
functional isomer butyl alcohol(C4H9OH)
2) NITRATION:
 Ethers are less reactive than alcohols due to
non-availablity of active hydrogen.
 Ethers donot react with alkali, acids, metals,
phosporous halides.
 Ethers donot oxidise and reduce easily like
alcohols under normal conditions
 Ethers reacts with acids, phosporous halides,
oxidising agents and reducing agents at high
temperatures but cannot react with metals like 3) FRIEDEL-CRAFTS REACTION:
sodium.
 Reactions of ether are classified into three types
on the basis of clevage of bonds.
i. ethyl groups which undergo substitution reactions
ii. ethereal oxygen which coordinates with electron
deficient molecules like Lewis acids.
iii. carbon- oxygen bond which shows some
cleavage reaction.
REACTIONS OF ETHYL GROUP.
HALOGENATION:Diethyl ether reacts with
chlorine or bromine to from halogen substituted
ethers.Hydrogens at  carbon atoms are easily
substituted in the dark condition.
REACTIONS OF ETHEREAL OXYGEN: HYDROLYSIS :
C2H5 – O – C2H5 + (O) 
 C2H5 – O – C2H5 + H2O  2C2H5OH
(steam)
C2 H 5  O  C 2 H 5
 ACTION OF PCl5 :
O
C2H5 – O – C2H5 + PCl5  2C2H5Cl+POCl3
(Peroxide)
ACTION OF ACETYL CHLORIDE AND ACETIC
ANHYDRIDE
FORMATION OF OXONIUM SALTS:
AlCl3
   C2H5 – O – C2H5 + CH3COCl  
C2H5–O– C2H5 + HBr   C 2 H 5  O

 C 2 H5  Br C2H5Cl + CH3COOC2H5
 H 
Diethyl oxonium C2H5 – O – C2H5 + (CH3CO)2O  
ZnCl2
bromide
2CH3COOC2H5
  
C2H5  O  C2H5  H2SO4  C2H5  O C2H5  HSO4

 H  ACTION OF CARBON MONOXIDE :
Diethyl oxonium hydrogen 0
BF3 /150 C
sulphate C2H5–O–C2H5+ CO   C2H5COOC2H5
500 atms
REACTIONS INVOLVING CLEVAGE OF C–O
BOND: (ethylpropionate)
ACTION OF SULPHURIC ACID : OXIDATION :
C2H5 – O – C2H5 + H2SO4(conc.)  

acid . K 2Cr2O7
C2H5O C2H5 + (O)   2CH3 CHO
C2H5OH + C2H5HSO4 acid . K 2Cr2O7
  2CH3COOH
ACT ION OF HYDROBROMIC ACID OR DEHYDRATION :
HYDROIODIC ACID:
0
Al2O3 / 360 C
In the cold condition C2H5O C2H5   2CH2 = CH2 + H2O
C2H5 – O – C2H5 + HI  C2H5I + C2H5OH
In the hot condition with excess of HI USES : ETHER IS USED IN/AS
 1. a solvent for oils, fats, waxes, plastics etc.
C2H5 – O – C2H5 + 2HI 
 2C2H5I + H2O
2. the extraction of organic compounds from
Here the cleavage is at alkyl oxygen due to aqueous solutions.
low reactiveity of aryl oxygen bond.In the cleavage 3. an inert medium for various reactions (ex.Wurtz
of mixed ethers lower alkyl group forms alkyl reaction) and preparation of RMgX
iodide. 4. an anaesthesia in surgery without causing any
dam age t o heart or lungs. (Recent ly,
If 30 alkyl group is present it forms tertiary halide
HALOTHANE is widely used for this purpose
as major product. since it is harmless and quick in action.
 CH OH+(CH ) Cl
(CH3)3-C-OCH3+HI 3 3 3 CF3CHCIBr ) (IUPAC name : 2-Bromo-2-
chloro-1,1,1-trifluroethane)
CH -OC H +HI  CH I+C H OH
3 2 5 3 2 5
5. NATALITE(mixture of Alcohol and Ether), a
OR OH
substitute for petrol
+ HX + R- X 6. Refrigerant along with dry ice (solid CO2 ) which
produces a temperature around 110 C
Alkyl aryl ethers are cleaved at the alkyl-oxygen bond
due to the more stable aryl-oxygen bond.
2. The compound which is not isomeric with diethyl
i) Enthrane (CHFCl  CF2  O  CHF2 ) and
ether is
isoflurane ( CF3CHCl  O  CHF2 ) 1) Butanone 2) Methyl propyl ether
are used as anesthetics in place of diethyl ether 3) 2-methyl propane-2-ol 4) Butanol-1
as the later one has slow effect. 3. The number of metameric ethers possible with
ii) Substituted anisols are used as flavourings and the formula C4H10O are
in perfumes due to their pleasant odour. 1) 4 2) 3 3) 2 4) 5
Eg : 4 The dialkyl derviative of H2O is
1) Alcohol 2) Ether 3) Ester 4) Keton
1.ANITHOLE NOMENCLATURE
5. Which of the following is a simple ether?
1) CH3 OCH3 2) CH3OC2H5
3) CH3CH2OCH(CH3)2 4) C2H5OC3H7
6. Ethers are isomeric with
1) Aldehydes 2) Acids 3) Alcohols 4) Ketones
7. CnH2n+2O is the general formula of ethers. To
is a constituent of anise seed. exhibit the functional group isomerism 'n' must
be minimum
1) 1 2) 2 3) 3 4) 4
8. The IUPAC name of C2H5 O C2H5
1) Diethyl ether 2) Ethoxy ethane
2.EQUGINOL 3) Ethoxy propane 4) Dimethyl ether
PREPARATION METHODS
9. Phenol on heating with NaOH followed by
is present in cloves. reaction with alkyl halide gives
1)Acetone 2) Ether
3) Ethanol 4) Acetic acid
10 Heating together sodium ethoxide and ethyl
chloridewill give [C.P.M.T.1981,Roorkee 1990]
3.VANILLIN 1) ether 2) ethyl alcohol
3) acetaldehyde 4) acetic acid
PREPARATION METHODS
11. Williamsons synthesis is used to prepare
is present in oil of vanilla been
1) Diethyl ether 2) PVC
3) Bakelite 4) Ethyl alcohol
12. Ethers are obtained by
1) Reaction of alkyl halide with dry ZnO
4.THYMOL 2) Reaction of alkyl halide with moist ZnO
3) Reaction of alkyl halide with dry Ag2O
4) Reaction of alkyl halide with moist Ag2O
PROPERTIES AND USES OF DIETHYL ETHER
is present in thyme and mint are used as
flavourings and in perfumes. 13. The compound in which hydrogen bonding is not
possible is
LEVEL - I
1) CH3OCH3 2) CH3CH2OH
MODEL QUESTIONS
3) H2O 4) CH3COOH
NOMENCLATURE
14. Following one is formed when a diethyl ether is
exposed to air for longer period
1. The following represents ether
1) Ethyl alcohol 2) Acetaldehyde
1) (RCO)2 O 2) RCOOR
3) Ethylene 4) Peroxide of diethyl ether
3) RCOR 4) ROR
15. The compound which has the lowest boiling point PREPARATION METHODS
is 27. In which of the following reations, the product
is an ether? (2005 E)
1) H2O 2) C2H5OH 3) CH3OH 4)CH3OCH3
16. Ethers on hydrolysis yield 1) C6 H 6  CH 3COCl / anhydrous AlCl 3
1) Alcohol 2) Aldehyde 3) Acid 4) Ketone 2) C2 H 5 Cl  aq.KOH
PRACTIACE QUESTIONS 3) C6 H 6  C 6 H5 COCl / anhydrousAlCl3

17. Diethyl ether on reaction with CO in specific 4) C 2 H5 Cl  C2 H 5 ONa
condition forms
1) Acetyl chloride 2) CO2 PROPERTIES AND USES OF
3) Ethyl propanoate 4) Acetic acid DIETHYL ETHER
18. With boiling water or steam diethylether gives
1) (C2H5)2 SO4 2) C2H5OH
3) CH2 = CH2 4) C2H5OH + C2H5HSO4 28. Assertion (A) : Ethyl alcohol reacts with alumina
19. Total number of lone pair electrons around at 260 0 C and gives di ethyl ether..
oxygens in diethyl peroxide is / are Reason (R) : Ethyl alcohol undergoes
1) 2 2) 3 3) 4 4) 0
dehydration.
20. Diethyl ether is used as
1) Anaesthetic 2) Solvent 3) Refrigerant 4) All 1) Both A and R are true and R is the correct
21. The safest general anaesthesia used at present explanation to A
is 2) Both A and R are true and R is not the correct
1) chloroform 2)diethyl ether
explanation to A
3) acetylene 4) halothane
22. Formula of halothane is 3) A is true but R is false
1) CF2Cl2 2) CF3Cl 3) CF3-CHClBr 4) (C2F4)n 4) A is false but R is true
29. Assertion (A) : Ethers behave as Lewis base in
LEVEL - II
MODEL QUESTIONS the presence of mineral acids in cold condition.
PREPARATION METHODS Reason (R) : Oxygen atom in ether has 4 lone
23. Excess of C2H5OH at 1400C reacts with conc. pairs of electrons.
H2SO4, then compound formed is 1) Both A and R are true and R is the correct
explanation to A
1) Diethyl ether 2) Diethyl sulphate
3) Ethylene
explanation to A
4) Ethylene hydrogen sulphate
3) A is true but R is false
24. Which of the following pairs of reagents will not
form ether 4) A is false but R is true
1) C2H5Br + C2H5ONa 2) C2H5Br + CH3ONa 30. Assertion (A) : Diethyl ether when boiled with
3) CH3Br + C2H5ONa 4) C2H5Br + HCOONa water gives ethyl alcohol.
25. What is Y in the following reactions Reason (R) : Diethyl ether is heavier than water.
(2001E) 1) Both A and R are true and R is the correct
C2 H 5 I  NaOC2 H 5  X  NaI explanation to A
X  2 HI  2Y  H 2O 2) Both A and R are true and R is not the correct
1) C2 H 6 2) C2 H 5 I explanation to A
3) C2 H 4 3) A is true but R is false
4) C2 H 5OC2 H 5 4) A is false but R is true
26. The reaction, Sodium alkoxide + Alkyl halide- 31. Diethyl ether reacts with cold. HI to give
>Ether+Sodiumhalide is called [C.P.M.T. 1990] 1) Ethyl iodide
1)Wurtz reaction 2) Ethyl alcohol
2) Kolbe’s reaction 3) Both 1 and 2
3) Williamson’s synthesis 4) Ethylene
4) Perkin’s reaction
0
32. Assertion (A) : Ethers behave as Lewis base in 42 .C2H5 – O – C2H5 + CO
BF3 /500 C
  X, here “X”
100 atm
the presence of mineral acids.
Reason (R) : Oxygen atom in ether is having is
lone pair electrons.
1) CH 3COOH 2) CH 3COOC2 H 5
explanation to A 3) CH 3CH 2 COOC2 H 5 4) C3 H 7 COOC2 H 5
2) Both A and R are true and R is not the correct 140 C 0
BF / 5000 C
43. 2CH 3CH 2OH   B.B + CO 3
 C.
100 atm
explanation to A H 2 SO4
3) A is true but R is false The functional groups present in B and C are

4) A is false but R is true respectively
33. Diethyl ether absorbs oxygen to form 1) Ester, ether 2)Ether, ester
[P.M.T.(Delhi) 1984] 3)Alcohol, ester 4)Ester, alcohol
1) acetic acid 2) acetaldehyde
3) ether peroxide 4) none 44. Oxygen atom of ether is [P.M.T.(M.P.)1988]
34. Ether reacts with conc. HCl or H2SO4 in cold to 1) Very active 2) replaceable
give 3) active 4) comparatively inert
1) Nitroso salt 2) Oxonium salt 45. Diethyl ether finds its use in medicine as
3) Alcohol 4) Hydrazone salt 1)anaesthetic 2)antiseptic 3) Hypnotic 4) Pain
35. Which of the following can not form Oxonium killer
salts with diethyl ether 46. Natalite is
1) HCl 2) HBr 3) H2SO44) H 2CO3 1) ether + petrol 2) alcohol + petrol
36. Which one of the following does not liberate 3) alcohol + ether 4) alcohol + KI + I2
hydrogen when treated with sodium metal 47. Which of the following is used as freezing
1) C2H5OH 2) CH3OCH3 3) CH3COOH mixture?
4) CH2OHCH2OH 1) mixture of ether and liquid CO2
37. Which of the following does not react with diethyl ether 2) mixture of ether and ethyl alcohol
1) C2H5ONa 2) AlCl3 3)BF3 4) HCl 3) mixture of ether and dry ice
38. Ethylene reacts with HBr forming ‘X’ which on 4) mixture of ethyl alcohol and dry ice
reaction with moist Ag2O gives ‘Y’. When ‘Y’ is LEVEL-III
heated with alumina at 3500C compound Z is MODEL QUESTIONS
formed. Then X and Z are 48. A compound X of the formula C2H6O, on reaction
1) Bromo ethane, ethanol with Na metal gave Y, X also reacts with PCl5 to
2)Ethanol, ethoxy ethane give Z. The product obtained in the reaction
3) Ethyl bromide, diethyl ether between Y and Z is
4)Bromo ethane, Ethene 1) CH3CHO 2) CH3COCH3
BF3 /5000 C 3) CH3COOC2H5 4) C2H5OC2H5
39.C2H5 – O – C2H5 + CO  X, here “X” is
100 atm
Alcl3 Aq. KOH
1) CH 3COOH 2) CH 3COOC2 H 5 49. CH2=CH2 + Hl   A  B
conc . H 2 SO4
3) CH 3CH 2 COOC2 H 5 4) C3 H 7 COOC2 H 5 
1400 C
 C, 'C' is
1)Ethoxy ethane 2) Ethanol 3) Ethanal 4)Acetone
PRACTICE QUESTIONS conc .H SO
Aq. KOH
40. Diethyl ether when heated to 3500C with Al2O3 forms 50. CH3-CH2 Cl   A  2
1400 C
4
B
1) Ethane 2) Ethene 3)Ethyne 4)Ethyl alcohol Al2 O3
  C. Then ‘C’
41. Formation of oxonium salts shows that ethers 3600 C
are is
1) Ethyne 2) Ethene
1) Basic in nature 2) Acidic in nature
3) Ethoxy ethane 4) Ethyl alcohol
3) Neutral in nature 4) Amphoteric in nature
Na
51. In the sequence of reactions (A) is : (A)  57. The major organic product in the reaction
C2 H5 I / heat HI / heat
(B)   (C)    C2H5I
1) Acetic acid CH 3  O  CH  CH 3  2  HI  Product, is
2) Methyl alcohol
3) Ethyl alcohol 4) Propionic acid 1.
CH 3O C| C2 H 5
I
52. Consider the f ollowing 2. ICH 2OCH  CH 3 2


in C 2 H 5 OK  C2 H 5 I   ‘X’ (pleasant
smelling liquid) (2005 M) 3. CH 3OH   CH 3  2 CHI
Which of the following reagents converts
ethylbromide to ‘X’ 4. CH 3 I   CH 3  2 CHOH
1)Na
2) Dry-Ag2O 58. In the following reaction
3) C2H5Cl Red ' P '
C2 H 5  O  C5 H 5  4  H    2 X  H 2 O ;
HI
4)dry-Ag powder
‘X’ is
53. Assertion (A) : Diethyl ether is used as general
1. ethane 2. ethylene
anaesthetia.
3. butane 4. propane
Reason (R) : Di ethyl ether produces
59. Tertiary butyl methyl ether on heating with H of
unconsciousness without effecting lungs.
one molar concentration gives
explanation to A 1. CH 3 I   CH 3  C  Cl
explanation to A 2. CH 3 I   CH 3 3 C  OH
3) A is true but R is false
4) A is false but R is true 3. CH 3OH   CH 3 3 C  I
LEVEL-IV 4. C2 H 5 I   CH 3 3 C  OH
MODEL QUESTIONS CH 3 COOC2 H 5 Na C2 H 5OH
60. CH 3 MgX 
H  ,H O
 A   B  C
H2 O
 propanol  the
2
54. CH3MgI      H ‘C’ is
missing reagent is
1. C2 H 5OC2 H 5 2. CH 3COOC2 H 5
1. HCHO 2. C2 H 5Cl
3. CH 3COOCH 3
3. C2 H 5OH 4. ethylene oxide
55. Formation of diethyl ether from ethanol is 4.  CH 3  3C  O  C2 H5
based on a 61. Which of the following compounds is resistant
1. homolytic fission reaction
to nuclephilic attack of OH uibs
2. hydronation reaction
3. dehydration reaction 1. Acetamide 2. Acetonitrile
4. dehydrogenation reaction 3. methyl acetate 4. diethyl ether
56 Which of the following is not cleaved by HI
even at 525K PRACTICE QUESTIONS
1. C6 H 5  O  CH 3 62. CH 2  CH 2  LiAlH 4   A , (A) is
2. C6 H 5OC3 H 7 O
3. 1. CH 3CHO 2. CH 3CH 2OH
O 3. CH 2  CH 2 4. CH 2  OH
4. C6 H 5  O  C6 H 5 CH 2  OH
63. Ethanol reacts with diazomethane to produce 69. An organic compound of molecular formula
1. CH 3OCH 3 C4 H10O does not react widh sodium with
2. C2 H 5OC2 H 5 excess of HI, it gives only one type of alkyl
3. C2 H 5OCH 3 iodide the compound is:

1. ethoxy ethane 2. 2-methoxy propane
4. C2 H 5OH
64. Complete combustion of ether gives 3. 1-methoxy propane 4. 1- butanol
LEVEL-V
1. C2 H 4 2. C2 H 2 MODEL QUESTIONS
70. Which of the following is the best procedure to
3. CO 2 and H 2 O 4. C2 H 5OH
make isopropyl methyl ether using the william
65. The product (D) in the following sequence of son’s method?
reactions is: 1) CH3 OH + (CH3)2CHOH+H2SO4 
HBr  
NaOH aq Na CH3I
C2H4    A   B   C   D 2) CH3OH (CH3)2CH CH2OH  H2SO4 
1. butane 2. ethane
3) CH 3ONa  (CH 3 ) 2 CHBr 
3. propane 4. ethyl methyl ether
66. The mixture of ethanol and sulphuric acid is 4) CH 3 I  (CH 3 ) 2 CHO  Na  
0
heated in a closed flast at 140 C . The flast 71 Select the in corrrect statement among the
would then contain following
1. H 2 SO4 and C2 H 5 O C2 H 5 only 1) The c-o-c bond angle in ether is 1100
2) Diethyl ether react with excess of HI to form
2. H 2O , H 2 SO4 and C2 H 5 HSO4 only ethyl iodide
3) Ethers and alcohols are functional isomers
3. H 2O , C2 H 5 HSO4 , C2 H 5 O C2 H 5 and 4) Ethers are Lewis base hence do not react
with bronsted acid like H2SO4
H 2 SO4 only 72. Which among the following statements about
4. H 2O , C2 H 5 O C2 H 5 , C2 H 5 HSO4 , ethers are correct?
1) Peroxide is obtained in presence of air
H 2 SO4 and C2 H 5 OH only
2) Ethers are weakly acidic
67. Ethers in contact with air for a long time from
3) Ethers from oxonium salt
peroxides. The presence of peroxide can be
4) Ethers from stable complexes with Lewis
tested by adding Fe 2 ions followed by the acids
addition of 73. Teritiary butyl methyl ether on reaction with
1. KCNS anhydrous HI gives an alcohol (A) and halide
2. Sn Cl2 (B) Which of the following statemen to is
3. Hg Cl2 4. KI correct?
1) Alcohol (A) performs Lucas test immediately
68. An equlimolar quantities of ethanol and
at room temperature.
propanol are heated with conc. H 2 SO4 . The
2) Halide (B)undergoes SN1 reaction most
products formed is/ are
readily
1. C2 H 5OC2 H 5 3) Alcohol (A) on heating with copper gives
2. C3 H 7 OC3 H 7 formaldehyde
3. C2 H 5OC3 H 7 4) Halide (B) On reaction with kCN mainly gives
4. all of these eliminated product.
74. CH3 -O-C(CH3)3 on reaction with CH3COCl in 78. MATCH THE FOLLOWING
List-I List-II
presence of Alcl3 gives (A) and
(Products when treated
C6H5-O-C(CH3)3 on reaction with cold HI gives with Hi in small amount)
(B).The compounds (A) and (B) are: a) C6 H 5  O  C 6 H 5 p) No product
A B
b) C6 H 5  O  C 2 H 5 q) C2 H 5 I
1) (CH3)3 C-Cl (CH3)3 C-I
2) CH3Cl (CH3)3 C-I c) C 2 H5  O  CH 3 r) CH 3 I
3) CH3OH C6H5-I
4) CH3COOCH3 (CH3)3 C-OH
75. C4H10O+PCl5  R1Cl+R2Cl+POCl3

R1Cl gives haloform test but R2Cl doesnot,
hence the original compound of the reaction is: 1. a-p, b-q, c-r, d-r,s
2. a-p, b-s, c-r, d-r
1) ethoxy ethane 2) 1- methoxy propane 3. a-q, b-p, c-s, d-r
3) 2- methoxy propane 4) isobutyl alcohol 4. a-r, b-q, c-s, d-p
76. The ether COMPREHENSION TYPE QUESTION
Carbon - oxygen bond in ethers can be cleaved
by halogen acids, sulphuric acid, phosphoruspenta
chloride etc., the cleavaege of C-O bond takes
place under drastic conditions with excess of
when treated with HI produces: hydrogen halide.
R  O  R  2HX  2RX  H 2O
If hydrogen halide is not taken in excess then a
molecule of alcohol and alkyl halide are formed.
373K
R  O  R  HI   R  OH  R  I
The order of reactivity of hydrogen halides towards
the given reaction depends on the bond strength
of halogenated acids, weaker is the H-X bond,
greater is its reactivity In case of unsymmetrical
ethers, the site of cleavage is such that the halide
77. (A) Tert butyl methyl ether is not prepared by is formed from the alkyl group which is tertiary,
the reaction of tert butyl bromide with sodium the halide formed is tertiary halide.
Indicate whether the following statements /
methoxide reactions are true or false.
(R) Sodium methoxide is a strong nucleophile 79. Hydrogen fluoride (HF) is not effective in ether
cleavage
1) Both A and R are true and R is the correct 1. True 2. False
explanation to A 80. The order of hydrogen halide reactivity is,

HI  HBr  HCl
1. True 2. False
explanation to A 81. In the reactions,
3) A is true but R is false R  O  R  HX  RX  ROX
4) A is false but R is true   
oxonium ion  R  O  R  is f ormed as
|
 H 
intermediate
1. True 2. False
KEY
1) 4 2)1 3) 2 4) 2 5) 1 18. C2 H 5  O  C2 H 5  H 2O  2C2 H 5OH
6)3 7) 2 8) 2 9) 2 10) 1 .. ..
11) 1 12) 3 13) 1 14) 4 15) 4 19. C2 H 5  O  O  C2 H 5
16) 1 17) 3 18) 2 19) 3 20) 4 .. ..
21) 4 22) 3 23) 1 24)4 25) 2 20. Given options are uses of diethyl ether.
26) 3 27) 4 28) 1 29) 3 30) 3
31) 3 32) 1 33) 3 34) 2 35)4 21. Halothane does not cause side effects.
36) 2 37) 1 38) 4 39) 3 40)2 22. CF3CHClBr
41) 1 42) 3 43) 2 44) 4 45) 1
46) 3 47) 3 48) 4 49) 1 50) 2 23. Ethyl alchol on dehydration at 140 0C with
51) 3 52) 2 53) 1 54. 4 55. 3 con H2SO 4 acids to give ethers.
56. 4 57. 4 58. 1 59. 3 60. 4 24. Alkyl halides cannot react with salts of
61. 4 62. 2 63. 3 64. 3 65. 4 carboxylic acids to give ether.
66. 4 67. 1 68. 4 69. 1 70. 4
71. 4 72. 1,3,4 73. 1 74. 1 25. X  C2 H 5OC2 H 5 ; Y  C2 H 5 I
75. 3 76. 1,4 77. 2 78. 1 79. 1
80. 2 81. 1 26. C2 H 5Cl  C2 H 5ONa  C2 H 5OC2 H 5  NaCl
ETHERS
HINTS 27. C2 H 5Cl  C2 H 5ONa  C2 H 5OC2 H 5  NaCl
1. General formula R-O-R 29. Ether behave like a Lewis base due to the
2. Alcohols and ethers are functional group
presence of l . p on oxygen atom
isomers.
3. CH 2  CH 2  O  CH 2  CH 3 , 30. C2 H 5  O  C2 H 5  H 2O  2C2 H 5OH
CH 3  O  CH 2  CH 2  CH 3 and 31. C2 H 5  O  C2 H 5  HI  C2 H 5 I  C2 H 5OH

32. Ether behave like a Lewis base due to the
CH 3  O  CH 3  CH 3  2
presence of l . p on oxygen atom.
4. R-O-R is ether
5. Same type of alkyl groups attached to 33.  
C2 H 5  O  C2 H 5 
O
C2 H 5  O  O  C2 H 5
oxygen atom.
34. With conc. HCl (or) H2SO 4 diethyl ether
6. Alchols are isomeric with ethers
from oxionium salt.
8. CH 2  CH 2  O  CH 2  CH 3 is 35. H 2CO3 is a weak acid
ethoxy ethane
36. Diethyl ether has no active hydrogen
NaOH
9. C6 H 5OH  C6 H 5  O  C6 H 5
C6 H 5Cl
37. Diethyl ether has no active hydrogen
10. C2 H 5Cl  C2 H 5ONa  C2 H 5OC2 H 5  NaCl

38. H 2C  CH 2  HBr  C2 H 5 Br
Ag 2O Al 2O 3
  C2 H 5OC2 H 5 
3500 C
 C2 H 4
12. 2 RX  Ag 2O  ROR  2 AgX 0
BF3 /150
39. C2 H 5  O  C2 H 5  CO 
500atm
 CH 3  CH 2  COOC 2 H 5
13. In ethers H-bond is absent
Al 2O 3
  O 40. 2C2 H 5  O  C2 H 5 
3500 C
 2C2 H 4  H 2O
14. C2 H 5  O  C2 H 5  C2 H 5  O  O  C2 H 5
41. Diethyl ether acts as Lewis base
15. In ethers H-bond is absent BF3 /150 0
42. C2 H5  O  C2H5  CO 
500atm
 CH3  CH 2  COOC2 H5
16. C2 H 5  O  C2 H 5  H 2O  2C2 H 5OH 43. A = Ether B = Ester

0
45. It is used as anaethesia as it does not
17. BF3 /150
C2 H 5  O  C2 H 5  CO 
500atm
 CH 3  CH 2  COOC 2 H 5
causing any damage to heart (or) lungs.
46. Alcohol + ether
C  C2 H 5ONa D  CH 3OC2 H 5
47. Mixture of ether and dry ice.
66. i)
Conc. H 2 SO4
48. X  C2 H 5OH , Y  C2 H 5ONa; Z  C2 H 5Cl
C2 H 5OH 
100 1100 C
  C2 H 5 HSO4  H 2O
Conc.H SO
49. A  C2 H 5 I , B  C2 H 5OH , C  C2 H 5OC2 H 5 ii) C2 H5OH  2 4
1400 C
C2H5OC2H5  H2O
(excess)
50. A  C2 H 5OH , B  C2 H 5OC2 H 5 , C  C2 H 4
Conc. H SO
51. A  C2 H 5OH , B  C2 H 5ONa, C  C2 H 5OC2 H 5 iii) C2 H 5OH  2
1700 C

4
 C2 H 4  H 2O
52. Conceptual 67. FeSO4
Ether peroxide   Ether +
53. X  C2 H 5OC2 H 5 Fe
H 2O2 
2
3 KCNS
 O   Fe  
Red colour
Conc . H 2 SO4
C 2 H 5 OH  CH 3CH 2 CH 2 OH    
54. 68.
C 2 H 5OC 2 H 5  C 2 H 5OC3 H 7  C3 H 7 OC3 H 7
55. Dehydration reaction 2 HI
69. C2 H 5OC2 H 5 
 2C2 H 5 I  H 2O
56. C6 H 5  O  C6 H 5 is not cleaved by HI even
 
at 525K due to steric factors. CH 3 I   CH 3  2 CH O Na 
70.
CH 3OCH  CH 3  2  HI  CH 3  O  CH  CH 3 2
57.
CH 3 I   CH 3  2 CHOH
71. Ethers react with H 2 SO4
58. X  C2 H 6 73. ‘A’ is a teritiany alcohol.
59. 74. A   CH 3 3  C  Cl
B   CH 3 3  C  I
75. A  CH 3  O  CH 2  CH 2  CH 3
60. A   CH 3 3  C  OH ,
B   CH 3 3  C  ONa,
76.
C   CH 3 3  C  OC2 H 5
61 Diethyl ether is resistant to nucleophilic
attack by OH  ions. 77. Alkoxide ions being both powerful nucleophiles
and bases would bring dehydrohalogenation
62. A  CH 3CH 2 OH of the teritiary alkyl halides to from alkenes
preferentially.
BF3
63. CH 2 N 2  C2 H 5OH 

C2 H 5OCH 3  N 2
* * *
64. Ethers on combustion produce CO2 , H 2O
65. A  C2 H 5 Br , B  C2 H 5OH

Alcohols, Phenols and Ethers

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NARAYANA SR.

AIEEE MATERIAL 137 ALCOHOL

Ethyl alcohol  C2 H 5OH  , CH 3  H 2 C

CH 3  CH 2  CH 2  OH  ; primary  H  CH 2OH 

COMMON SYSTEM OF NOMENCLATURE:

CH 3 Methyl alcohol  CH 3OH  ,

Compound Common Name IUPAC name

sp 3 hybridised orbital of carbon with a CH 3 CH 2 X  NaOH ( aq )  CH 3 CH 2 OH  NaX

sp 3 hybridisecd orbital of oxygen. depicts Where X  Cl , Br , I

obtained from starchy grains. (or)

iii) FROM ACETALDEHYDE:

v) FROM ETHYLENE (On large scale) ethylene is

hydrogen sulphate ( C2 H 5 HSO4 ).

RCOR ' 4

 The industrial alcohol or rectified spirit is

 2) Industrial methylated spirit which is 95%

Test Primary alcohol Secondary alcohol Tertiary alcohol

2) Victor Meyer’s : Red colouration Blue colouration No colour is produced

3) Catalytic Aldehyde, H2 is Ketone, H2 is produced Dehydration takes place

RCOOH Mixture of ketone contains lesser

 As number of electron releasing alkyl groups

CH 3COOC2 H 5  H 2O  ACTION WITH THIONYL CHLORIDE

Note : Order of reactivity HI > HBr > HCl > HF

Thus, the relative ease of dehydration of alcohols i) CH 3  CH 3  OH  H 2 SO4 

CH3CHO  CH3COOH(O) CH 3  CH 2   O|  H  ..

1) ethylene bromide 2) ethylidene bromide 1) Acetone 2) Tertiary butyl alcohol

146. Which of the following Order regarding acidity OH

and CH 3CH 2COOH . The alcohol is C H MgI / HOH

4. CH 3CH  OH  CH 2CH 2CH 3

CH 3 Molecule M and reqgent ‘R’ respectively are:

96. 3C2 H 5OH  PCl

102. 121. 20  or  30 alcohols on oxidation give ketone

133. A  CH 3COOH , B  C2 H 5OH  

175. C2 H 5OH gives hydrogen gas with sodium

Molecule Common name IUPAC name

METHODS OF PREPARATION OF PHENOL

350o C & 300 atm

3) From diazonium salt :

4) From benzene sulphonic acid :

cumene hydroperoxide  CH 3COCH 3 >

The greater the pKa value, the weaker the acid.

pKa Values of some Phenols and Ethanol

Compound Formula pKa

Dichloro carbene ( : CCl2 ) is the attacking

The yield of the reaction product is poor. ii) + : CCl2 

2.2,4,6-trinitrophenol 2. dichlorocarbene (: CCl 2 )

Phenol  Zn conc.HNO3

4) d) p-cresol s) 4-methyl phenol

41. 1 42. 4 43. 2 44. 1

6. PKa of phenol = 10 18. Phenol PKa = 10

7. Picric acid 4-nitro phenol PKa = 7.1

8. 2, 4, 6 - trinitro phenol 19. Phenol PKa = 10.0

40. Solol is obtained form salicyclic acid and phenol

ETHERS  STRUCTURE OF FUNCTIONAL GROUP

C6 H 5OCH 3 Anisole Anisole  CH 3  O  C  CH 3  NaBr

C2H5 – O – C2H5 + H2SO4(conc.)  

PRACTIACE QUESTIONS 3) C6 H 6  C 6 H5 COCl / anhydrousAlCl3