ALCOHOLS

 Tertiary Alcohols (30): In these alcohols the –

SYNOPSIS
OH group is attached with tertiary carbon atom
 Alcohols are the hydroxyl derivatives of They posses a general formula R3C-OH
hydrocarbons i.e., obtained by the replacement CH 3
of one or more H atoms R-H  -H
+OH
 R-OH
C2 H5 - C - OH
 The compound in which a hydroxyl group is Eg: Tert. amyl alcohol
attached to a saturated carbon atom are called CH 3

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alcohols.
Allyl alcohols: In these alcohols the –OH group
Eg:- 1)CH 3OH 2)C2 H 5OH is attached a sp3 hybridized carbon atom next to
 The compounds in which hydroxyl group is the carbon – carbon double bond i.e. to an allylic
attached to an unsaturated carbon atom of a carbon.
double bond are called ‘enols’.Eg;- H 2C=CH-OH
Classification: Alcohols are classified
according to the number of hydroxyl groups Eg: H 2C = CH-CH 2 -OH
present in their molecules. Allyl alcohol But-3-en 2-ol
 Monohydric alcohols contain one –OH group, Benzyl Alcohols: In these alcohols, the –OH
dihydric two and trihydric three, respectively. group is attached to sp3 hybridised carbon next
 Monohydric alcohols are further classified to an aromatic ring.
H
according to the hybridization of carbon atom
CH2OH C – OH C – OH
to which the –OH group is attached.
Compounds containing Csp -OH bond:
3 Eg:- CH3 CH3

In these alcohols the –OH group is attached to a Primary Secondary Tertiary

sp3 hybridised carbon atom of an alkyl group. 
These are further subdivided as follows
 Primary Alcohols (10): In these alcohols the
–OH group is attached with primary carbon atom
They posses a general formula RCH2OH. R may
be H in the first member and alkyl group in the
rest of the members.
Eg: HCH2OH Methyl alcohol
Hence, allylic and benzylic alcohols may be
primary, secondary or tertiary.
Compounds containing Csp2-OH bond:
In these alcohols, the –OH group is attached to
a carbon atom of the double bond, i.e., vinylic
carbon or to an aryl carbon.
Eg: H2C=CH-OH – Vinyl alcohol
CH 3

OH
CH3CH2OH Ethyl alcohol OH

CH3CH2CH2OH n – propyl alcohol

 0
Secondary Alcohols (2 ):In these alcohols the Phenol
O-Cresol
–OH group is attached with secondary carbon
Note:
atom.They posses a general formula R2CHOH.  When two or more hydroxyl groups are attached
CH 3 - CH - CH 3 CH 3 - CH - CH 2 - CH 3 to the same carbon atom, the compound is
Eg: usually unstable. This unstable compound
OH OH looses a water molecule and gets converted to a
Isopropyl alcohol Secondary butyl alcohol stable compound.
 IUPAC system: According to this system
OH  H2O
C 
 C=O alcohols are called alkanols.
OH Eg:- CH3OH Methanol
CH3CH2OH Ethanol
Unstable
CH3 - CH 2 - CH 2 - CH 2 - OH Butan – 1 - ol
 But inspite of having two hydroxyl groups to the
same carbon atom, chloral hydrate CCl3CH(OH)2 Isomerism: Alcohols may exhibit chain,
is a stable compound. The unusual stability of chloral positional and functional isomerism.
hydrate has been attributed to the –I effect of  Functional isomers of alcohols are ethers.
chlorine and to the formation of intramolecular CH 3 –CH 2 –CH 2 –CH 2 CH 3 –CH–CH 2
Eg: and | |
hydrogen bonds. OH CH 3 OH

are chain isomers

CH 3 –CH 2 –CH 2 –CH 2 CH 3 –CH–CH 2 –CH 3

OH
and OH
are position isomers
 CH3–CH2–OH and CH3–O–CH3 are functional
Nomenclature: There are three systems of isomers.
naming the alcohols.  Unsaturated alcohols and carbonyl compounds
are tautomers.
Common system: In this system alcohols are
named as alkyl alcohols i.e., the word alcohol CH3 –C=CH 2 and CH3 –C–CH 3
OH O
are tautomers.
is added to the name of alkyl group.
 In higher members, it is always indicated  Alcohols containing chiral centres can exhibit
whether the –OH group is attached to primary, optical isomerism.
secondary or tertiary carbon atom by prefixing  The simplest monohydric alcohol that can
‘n’ for primary, sec for secondary and tert for exhibit enantiomerism is butan–2–ol.
tertiary.
H
Eg; CH3OH Methyl alcohol |
CH3CH2OH Ethyl alcohol CH 3  C  OH
CH3CH2CH2OH n-propyl alcohol |
OH C2 H 5

| W.E-1:Identify the most stable conformer of glycol.

Sec.butyl alochol
CH 3  CH 2  CH  CH 3 Sol. Gauche form of glycol is most stable. This is
Carbinol system: The simplest monohydric due to intramolecular hydrogen bonding.
alcohol CH3OH is called carbinol.
 All other members are considered its alkyl O H
derivatives. O–H
 The alkyl groups attached to the carbon atom H
carrying –OH group are named in alphabetical
order.
H H
Eg:- CH3OH CH3CH2OH
Carbinol Methyl carbinol
H

Dimethyl carbinol W.E-2:Glycerol does not contain ....alcoholic group

Sol. Tertiary
 Preparation methods of Alcohols: 
R  Mg  X  R1CHO 
H / H 2O
 R  CH  R1
1. From Alkenes: It is an electrophilic addition
|
reaction .
OH
H 2 C = CH 2 + H 2 O   CH 3 - CH 2 - OH
+
H
20 alcohol
 In this reaction there is a possibility of formation R
of carbocation . |

OH R  Mg  X  R1COR11 
H / H 2O
 R1  C  R11
CH 3 - CH - CH = CH 2 
HOH
H+
 CH3 - C - CH 2 - CH 3 |
OH
CH 3 CH 3 0
3 alcohol
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3 methyl prop 2 ene 2 methyl 2 butanol

By hydroboration oxidation of alkenes:It
is used to get primary alcohol from terminal
alkene.
 Reagent used in this method is diborane
followed by alkaline H2O2.
 The product obtained in this reaction seems to
follow anti markownikoff’s addition of water
over alkene.
 Hydroboration is regioselective.
 With unsymmetrical alkenes, the boron atom
bonds to the less substituted carbon atom.
Aqueous alkali hydrolysis of alkyl halide:
This reaction is a nucleophilic substitution
reaction and in the reaction nucleophile HO- ion
becomes hydrated to give the substituted
product. R - Br + KOH (aq)  R - OH + KBr
Reduction of Aldehyde and Ketone:
Aldehyde on reduction with LiAlH 4 gives
primary alcohol, whereas ketones gives
secondary alcohols.
H H3O R – CH – OH
 R – CH – O 
R – C = O    2

BH
H 3C  CH  CH 2 
3
 CH 3  CH  CH 2
H H
| | Primary
Aldehyde alcohol
H BH 2
 In this reaction borane serves as electrophile.  H 3O 
H
R – C = O  R – CH – O   R2 – CH2 – OH
Oxymercuration demercuration of
Alkenes: The addition of H2O over alkene R R
Secondary
without rearrangement follows Ketone alcohol
markownikoff’s rule. In this reaction reducing agent may be
 Reagent used is mercuric acetate followed by 1) Zn/ HCl 2) Na/C2H5OH
reduction with NaBH4.
3) LiAlH4 4) NaBH4
R  CH  CH 2 
1) Hg ( OAc )2 , H 2O2 , THF
2) NaBH OH 
 R  CH  CH 3 Note:NaBH4 is a selective reducing agent. It
4,

| reduces only aldehydes, ketones, carboxylic

OH
(  Ac   C  CH 3 )
||
O
Note:No carbocation is formed in hydroboration
oxidation reaction and oxymercuration and
demercuration reaction.
From Grignard’s reagent: Treatment of
carbonyl compound with RMgX followed by
acids without affecting C = C, N = N, esters,
nitriles and nitro group.
 LiAlH4 is used to reduce carbonyl compounds,
acids, esters, acid chlorides and anhydrides to
alcohols without normally affecting the double
bond. However, the double bond gets reduced
when a phenyl group is present at β position.
 

aicidic hydrolysis forms an alcohol with new Eg: C6 H 5  C H  C H  COOH 

LiAlH 4

C6 H 5  CH 2  CH 2  CH 2  OH
carbon – carbon bond.
 Hydrolysis of Ester: Esters on hydrolysis Absolute alcohol is 99.6 to 100% pure ethyl
gives acid and alcohol. alcohol.
RCOOR1 + H 2 O H
 R-COOH + R1 - OH
+
From Starch: A suspension of starch is made
or HO-
by heating with water at 50°C.
 Alcohols being more volatile than acid an hence  Germinated barley called malt is added. Malt
it can easily be separated by distillation. contains diastase, which converts starch to
Ester hydrolysis involves the cleavage of C–O
maltose.
– C – OR
1 2(C6H10O5)n + nH2O  DIASTASE
 nC12H22O111
bond of  The mixture is cooled to 30°C and yeast is
O added. An enzyme, maltase produced by yeast
By Fermentation:Decomposition of large converts maltose into glucose.
compounds into simple compounds by enzymes C12H22O11 + H2O  MALTASE
 2C6H12O6
derived by mirco organisms like yeast is called
 Zymase converts glucose to ethyl alcohol.
fermentation.
 Enzymes are biocatalysts which are non living C6H12O6  ZYMASE
 2CH3CH2OH + 2CO2
nitrogenous compounds.  Methyl alcohol is prepared from water gas
 They catalyse reactions taking place in living enriched with H 2 in presence of oxides of
organism and act as specific catalysts. Yeast is chromium and zinc. It is also prepared by the
a single cell microorganism. partial oxidation of methane.
From Molasses: Molasses is the mother liquor CO + 2H2 
ZnO, Cr2 O3 , 200atm,600K
 CH3OH
left after seperation of sugar from sugar cane
  2CH3OH
0
2CH4 + O2 Cu, 250 C,100atm
juice.
 It is black and viscous and still contains 20-40%  Mineralised methylated spirit : 90%
sucrose. rectified spirit +9% methyl alcohol +1%
 It is diluted with water so that the percentage of petroleum oil and a purple dye.
sugar in it is 10%.  Industrial methylated spirit : 95% rectified
 Then H2SO4 is added to maintain the pH at 4. spirit +5% methanol.
 Ammonium sulphate or phosphate is added  Denatured alcohol is unfit to consume as it
which serves as food for yeast. Then yeast is contains CuSO4, pyidine or methanol. Industrial
added and the mixture is taken and retained in alcohol is also made unfit for drinking by adding
large wooden tank for 2–3 days at 30°C – 40°C. methyl alcohol.
 An enzyme, invertase produced by yeast
converts sucrose into glucose and fructose. W.E-3:How acetylene is converted to ethyl alcohol?
C12H22O11 + H2O  INVERTASE
 C6H12O6 + Sol. Acetylene on hydration gives acetaldehyde,
C6H12O6 which on reduction gives ethanol.
 Another enzyme, zymase converts glucose and HC  CH + H 2 O 
HgSO4
 CH3 - CHO 
LiAlH 4
 C2 H5OH
H 2SO4
fructose into ethyl alcohol.
C6H12O6  ZYMASE
 2CH3CH2OH + 2CO2 W.E-4:How benzyl alcohol is obtained from benzyl
 The fermented solution contains 6–10% ethyl chloride ?
alcohol and is called wash or wort. Sol. Benzyl chloride on base hydrolysis gives benzyl
 This dilute solution on fractional distillation alcohol.
gives rectified spirit containing 93-95% alcohol.
 Generally 95-96% alcohol is called as Rectified CH2Cl CH2OH
spirit (or) industrial alcohol. 
aq.NaOH

 It is converted to absolute alcohol by drying on
treating with quick lime and then over calcium.
 Physical properties of Alcohols:
 Alcohols have higher boiling points than
hydrocarbons, ethers, aldehydes and ketones of
comparable molecular masses. Alcohols have
greater intermolecular attractions arising due to
intermolecular hydrogen bonds. The tendency
of formation of hydroegn bonds is
10  20  30 alcohols
 The boiling points of alcohols increase with an
increase in molecular mass arising due to vander
Waals forces.
 Alcohols and ethers are functional isomers but
the boiling point of alcohol is greater than
corresponding ether due to formation of
intermolecular hydrogen bonds.
Eg. Order of boiling points : Methanol < Ethanol
< Propanol < Butanol.
 In case of alcohols with same alkyl group,
boiling point decreases with increasing
branching.
Eg. n–Butyl alcohol > Iso butyl alcohol > tert.
Butyl alcohol.
 Alcohols are soluble in water due to hydrogen
bonding between molecules of alcohol and
water.
 Solubility in water decreases with an increase
in the size of non polar hydrophobic alkyl group,
which resists dissolution.
Eg. Order of solubility : CH3CH2OH >
CH3CH2CH2CH2OH > CH3(CH2)4CH2OH
 Among isomeric alcohols, solubility decreases
with increase in surface area.
Eg. tert. Butyl alcohol > Isobutyl alcohol >
n–Butyl alcohol.
 The boiling point of methanol is 670C.
Methanol is highly poisonous in nature.
Ingestion of even small quantities can cause
blindness and large quantities causes even death.
 Ethanol is a sweet smelling colourless liquid. It
is soluble in water as well as organic solvents.
Its boiling point is 78.1°C
 Ethyl alcohol has burning taste and burns with
blue flame. A mixture of 95.6% ethyl alcohol
and 4.4% water forms constant boiling mixture
called as azeotropic mixture. Since it forms an
addition compound with CaCl2, it cannot be used
for drying ethyl alcohol.
 Ethyl alcohol is obtained from starchy grains and
so is called as grain alcohol and as it is a constituent
of wines, it is called as spirit of wine
Chemical properties: The hydroxyl group
present in alcohols is a very reactive group and
the characteristic reactions of alcohols are the
reactions of –OH group
 The reactions of hydroxyl group consists of
either cleavage of C – O bond of the cleavage
of O – H bond.
 ‘C – O bond is weaker in the case of tertiary
alcohols due to +I effect of alkyl groups while
O – H bond is weaker in primary alcohols as
electron density increases between O – H bond
and hydrogen tends to separate as a proton.
 Hence in O – H cleavage, the order of
reactivity is Primary > Secondary > Tertiary
and in C – O cleavage the order of reactivity
is Tertiary > Secondary > Primary.
 During O – H cleavage proton is given out
showing that alcohols are acidic in nature.
 However, alcohols are weaker acids than water.
This is because the alkyl groups in alcohols have
+I effect.
 Hence the following order is followed in the
acidic nature of alcohols.
CH 3OH > Primary alcohol > Secondary
alcohol > Tertiary alcohol
 In general the reactions of alcohols may be
divided into following three categories.
(a) Reactions involving the cleavage of O – H
bond [C – O – H]with substitution or removal
of hydrogen as proton(i.e., alcohols act as
nucleophiles)
(b) Reactions involving the cleavage of carbon
– oxygen bond [C – OH] with substituion or
removal of –OH group (i.e., aclohols acts as
electrophiles).
(c) Reactions involving both the cleavage of
alkyl and the hydroxyl groups of the alcohol
molecules.
 Reaction with Metals: Alcohols react with W.E-6:Assertion (A): Dehydration of alcohols can be
metal to form metal alkoxide and evolve H2. carried out with Conc H 2SO4 but not with
This reaction is acid – base reaction. conc.HCl.
1 Reason (R) : H2SO4 is dibasic while HCl is
R - OH + M  R - OM + H 2 (M = Na, K etc)
2 monobasic.
1
1) Both A and R are true and R is the correct
Eg: C 2 H 5OH + K  C 2 H 5OK + H 2 explanation to A
2
2) Both A and R are true and R is not the correct
 Metal hydrides react with alcohol and evolve
explanation to A
H2 gas.
3) A is true but R is false
R-OH + MH  R - OM + H2 (M = Na, K etc) 4) A is false but R is true
Dehydration of Alcohols: Alcohols when Sol. ‘2’
heated in presence of conc. W.E-7:Hydroboration-Oxidation of CH 3CH  CH 2
0
H2SO4 (170 – 180 C) or H3PO4, Al2O3 or P2O5 produces.
undergoes dehydration to form alkene.
1. CH 3CH 2CH 2OH 2. CH 3CH  OH  CH 3
Eg: CH 3 - CH 2 - OH   H 2 C = CH 2 + H 2O
0
H SO ,160 C
2 4

 Order of ease of dehydration of alcohols: 3. CH 3CH  OH  CH 2OH 4. CH 3COCH 3

30 > 20 > 10 Sol. ‘1’
 Stability order of alkene: More substituted
W.E-8:The compound which gives the most stable
alkene is more stable (due to hyper conjugation)
carbonium ion on dehydration.
 Ease of dehydration:
CH 3
CH 3 CH CH 2OH CH 3 C OH
OH > OH> OH 1.
CH 3
2.
CH 3

 Alcohols when heated with conc. H2SO4 at 383 3. CH 3CH 2CH 2CH 2OH
0
K (110 C) give dialkyl sulphate and at 413 K
(1400C) give ether. At 443 – 453 K (170 – CH 3 CH CH 2CH 3
0
180 C) they give alkene. 4.
OH
 Alcohols when heated with alumina (Al2O3) at
Sol. ‘2’.
513 – 523 K (240 –2500C) give ether and at 633
K (3800C) give alkene. Note:Primary alcohols undergo dehydration by E2
 No rearrangement takes place in E2 mechanism. mechanism(tertiary or neo carbon is not present
at  poistion) while secondary and tertiary
W.E-5: Predict the major product of dehydration alcohol undergo dehydration by E1 mechanism.
of each of:  Regardless the type of alcohol, however, strong
(A) (CH3)2C(OH)CH2CH3 acid is always needed to protonate the O atom
(B) (CH3)2CHCH(OH)CH3 to form a good leaving group.
(C) (CH3)C(OH)CH(CH3)2  With 10 alcohols, however, loss of the leaving
group and removal of a proton occur at the same
CH3 H3C CH3 time, so that no highly unstable primary
(A) and (B) H3C C CHCH 3 (C) C C carbocation is generated.
Sol.
H3C CH3
 Rearrangement in the Alicyclic ring:  Primary alcohols are oxidized to either aldehyde or
In case of cyclic alcohols whenever a to carboxylic acids by replacing either one or two
carbocation is formed outside the next carbon C – H bonds by C – O bonds.
atom of a ring, ring expansion may takes place.
Examples of ring expansion: R - CH 2 -OH 
[O]
 R-CHO 
[O]
 R-COOH
 Secondary
2 alcohols
6
are oxidized to ketones by
2 + + + one C – H bond by a C – O bond.
replacing
3
H 3 1 1
OH   6
R 2 - CH 5- OH   R2- C = O
 H2O Bond breaks at C1 and C5 [O]
4 5 New bond forms at C5 and C6 4
–
1° Carbocation
 Tertiary alcohols have no H atom on the carbon
2° Carbocation

with OH group, so they are not oxidized.

–H+

2 6
2 + + 3
+

3 1 1
OH 
H
 6
Bond breaks at C1 and C5
R
 H2O
4 5 New bond forms at C5 and C6 4 5 Cyclo hexene
 O 
– 2° Carbocation
R – C – OH  No reaction
1° Carbocation
–H+
R

Carbon bearing –OH

Cyclo hexene group do not have
hydrogens
Reaction with HX: The reaction of alcohols
with HX (X = Cl, Br) is a general method to  Oxidation with Ceric ammonium nitrate (CAN)
prepare primary, secondary and tertiary alkyl is a very selective reagent for the mild oxidation
halide. of primary alcohol. The reagent also oxidise
aromatic methyl group into – CHO.
CH 3 - CH 2 - OH  
HBr
 CH 3CH 2 Br + H 2 O
CH 3 - CH 2 - OH 
CAN
 CH 3 - CHO
 More substituted alcohols usually react more
CH2 – OH  HCO
rapidly with HX. HCO
CAN
3 3 CHO
 Order of reactivity of alcohols with HX is
Tertiary > Secondary > Primary.  Manganese dioxide (MnO2) is selective and
 Primary alcohols form R – X by SN2 reaction mild oxidant. It is specific for allylic and
while secondary and tertiary alcohols form R–X benzylic alcohols.
by SN1 reaction.
Because carbocation is formed in SN1 reaction H 2 C = CH - CH 2 - OH   H 2 C= CH - CHO
MnO 2

of secondary and tertiary alcohols with H X , Oppenauer Oxidation: The reaction involves
carbocation rearrangement is also possible. the oxidation of secondary alcohols with a
ketone and a base to the corresponding ketone
Reaction with PX5: The treatment of PX5 with
of the alcohol.
primary and secondary alcohols forms an alkyl
halide. R 2 - CH - OH 
Al(OCMe)
CH -CO-CH
 3
3
3

R- OH + PCl3  R - Cl + H 3PO3 R - CO - R + CH 3 - CH(OH) - CH 3

R- OH + PCl5  R - Cl + POCl3 + HCl Haloform reaction: Compounds having methyl

keto group react rapidly with halogen in presence
Oxidation of Alcohols: Alcohols are of a base to form haloform.
oxidized to carbonyl compounds depending on R - CO - CH 3 + 3X 2 + 4NaOH  CHX 3 + RCOONa
the type of alcohol and reagent.
 Ethyl alcohol gives positive haloform test.
 Oxidation occur by replacing C – H bond on NaOH  Cl2
the carbon bearing OH group by C – O bond. C2 H 5OH  NaOCl   CHCl3  HCOONa
 Secondary alcohols having –CH(OH)-CH3 group CH3
also give haloform test. |
2,2-dimethylpropan-1-ol CH3  C  CH 2 OH Primary
|
Esterification reaction: Treatment of a CH3
carboxylic acids with an alcohol in presence of
an acid catalyst forms an ester. This reaction is CH3
|
called a Fischer esterification. 2-methylbutan-2-ol CH3CH 2  C  OH Tertiary
|

R- COOH+R1 - OH  RCOOR1 + H 2 O
H 2SO 4
CH3
 This reaction is an equilibrium. According to
W.E-10:How are the following conversions carried
Lechatilier’s principle, it is driven to the right
out ?
excess of alcohol or by removing the water is it
is formed. (i) Propane   propan-2-ol
Note:Esterification of a carboxylic acids occur in the (ii) Benzyl chloride  Benzyl alcohol
presence of acid but not in the presence of base.
(iii) Ethyl magnesium chloride 
 Propan-1-ol
Base removes a proton from the carboxylic acids
forming a carboxylate anion, which do not react (iv) Methyl magnesium bromide  
with an electron rich nucleophile. 2-Methylpropan-2-ol
Br2
Sol. (i) CH 3  CH 2  CH 3   CH – CH – CH Br
Uses of Ethanol: propane  HBr 3 2 2

1. Ethanol is used to prepare alcoholic beverages CH3  CH  CH3

2. Ethanol is used as solvent in perfumes, paints, KOH (alc.)

 CH 3  CH  CH 2 
2  H O |
OH
varnishes, dyes etc. propene
propan  2  ol

3. Ethanol is used as preservative for biological

CH2Cl CH2OH
specimens.
4. Ethanol is used to prepare acetaldehyde, acetic
acid, chloroform, iodoform, ethyl iodide etc. KOH(aq.)

(ii) + KCl (aq)
5. Ethanol is used as antifreeze in car radiators,
spirit lamps and as antiseptic. Benzyl chloride Benzyl alcohol

6. Ethanol is used to prepare power alcohol and

H
natalite, a substitute to petrol. |
(iii) C 2 H5 MgCl + H  C  O 

MISCLLANEOUS SOLVED EXAMPLES ethyl magnesium methanal
chloride
W.E-9:Draw the structures of all isomeric alcohols
H H
of molecular formula C5H12O and give their OH
H 2O
H – C – OMgCl  H – C – OH + Mg
IUPAC names. Classify them as primary,
secondary and tertiary alcohols. C2H5 C2H5
Cl
Sol. The structures, IUPAC names and the propan-l-ol
classification of all isomeric alcohols of
molecular formula C5H12O are : CH3
|
(iv) CH3  C  O + CH3 MgBr ether


Pentan-1-ol CH3 -CH 2 -CH 2 -CH 2 -CH 2OH Primary propanone methyl magnesium
(acetone) bromide

Pentan-2-ol CH3  CH 2  CH 2  CH  CH3 ; Secondary CH3 CH3

| | OH
OH |
H
CH3  C  OMgBr 2 O
 CH3  C  OH + Mg
| Br
|
Pentan-3-ol CH3  CH 2  CH  CH 2  CH3 Secondary CH3 CH3
| 2  methylpropan  2 ol
OH (tert  butyl alcohol)
 METHODS OF DISTINGUISHING BETWEEN PRIMARY, SECONDARY
AND TERTIARY ALCOHOLS:

Test Primary alcohol Secondary alcohol Tertiary alcohol

Lucas reagent Does not form turbidity Turbidity is formed in 5 Turbidity is formed
Testing with a mixture of at room temperature to 10 minutes immediately
conc. HCl and anhyd. (turbidity is obtained
ZnCl2 only upon heating)

Catalytic dehydro- RCH2OH  Cu R R

RCHO RCHOHR  Cu
RCOR
3000 C 3000 C
genation R–C–CH3 Cu
300C
 R–C=CH2
(vapours of alcohol are An aldehyde is obtained A ketone is obtained OH
passed over hot metal)
An alkene is obtained
Oxidation RCH2OH RCHOHR R3COH (with less
(with acidified    number
RCHO RCOR RCOR of
permanganate or carbon
dichromate solution)    atoms)
RCOOH Two acids Two acids
(same number of carbon (with less number of (with less number of
atoms in the three carbon atoms) carbon atoms under drastic
compounds) conditions)

Victor Meyer test Nitrolic acid gives red Pseudonitrol gives blue No colour is obained
colour colour
Alcohol
HI RCH2OH R2CHOH R3COH
HI HI HI
Alkyl iodide
AgNO2 RCH2I R2CHI R2CI
Nitro compounds AgNO2 AgNO2 AgNO2
(i) HNO2 RCH2NO2 R2CHNO2 R2CNO2
HNO2 HNO2 HNO2
(ii) NaOH
NaOH
R–CH–NO2 R2C–NO2 No reaction

NO NO
NaOH
R–C–NO2 Blue colour

NOH
NaOH
R–C–NO2
– +
NONa
Red colour
 13. Primary,secondary and tertiary alcohols are
LEVEL-I (C.W) distinguished by
1) oxidation method 2) Lucas test
NOMENCLATURE 3) Victor Meyer’s method 4)all the above
1. 2,4-dimethyl -3-pentanol is a 14. The reaction between an alcohol and
1) primary alcohol 2) secondary alcohol carboxylic acid leads to the formation of
3) tertiary alcohol 4) dihydric alcohol 1) Aldehyde 2) Ester 3) Ketone 4) Paraffins
2. Which of the following is a tertiary alcohol 15. Alcoholic is beverages contain
1)  CH 3 2 CHCH 2OH 2) CH 3CH 2CH 2CH 2OH 1) Glycerol 2) Ethyl alcohol
3) Methyl alcohol 4) Isopropyl alcohol
3) CH 3CH 2CH 2OH 4)  CH 3 3 COH
16. Ethyl alcohol on oxidation with acidified
PREPARATION K2Cr2O7 gives
3. The enzyme which converts glucose to 1) CH3COCH3 2) HCOOH
ethylalcohol is 3) CH3COOH 4) HCHO
1) zymase 2) invertase 3) maltase 4) diastase Pd  BaSO4 / Quinoline
17. H  C  CH  H 2  A
4. Whichof the following is Lucas reagent
1) ammonical silver nitrate 2) Br2 / CCl4 
HCl
B KOHaq
C
Here the ‘C’ is
3) dry ZnCl2 / con. HCl 4) alk.KMnO4 1) Propane 2) Ethanol 3) Ethyne 4) Ethylene
5. Ethyl alcohol is the hydrolysis product of 18. A compound (X) of molecular formula C3H8O
1) C2H5Cl 2) CH3CHO 3) C2H4 4) C2H5 MgI can be oxidized to a compound of molecular
PROPERTIES formula C3H6O2 (Y), (X) is most likely an
6. 95% ethyl alcohol can be converted to 1) Aldehyde 2) Alcohol
100% ethyl alcohol by the following 3) Ether 4) Both 2 and 3
1) Magnesium chloride 2) Calcium oxide 19. Which of the following gives Iodo form test
3) Magnesium phosphate 4) Magnesium sulphate 1) CH3—CH2—CH2—OH 2) CH3—CH2—OH
7. In wash or wort possess ---- percentage of 3) CH3—CH(OH)—CH3 4) Both 2 and 3
ethyl alcohol 20. There are three alcohols x,y,z which have 2,1
1) 95% 2) 100% 3) 66.9% 4) 6 - 10% and 0 alpha hydrogen atom(s) respectively.
8. CaCl2 + C2H5OH —> CaCl2. xC2H5OH. ‘x’ is Which does not give Lucas Test immediately
1) 3 2) 6 3) 2 4) 1 1) x 2) y 3) z 4) all the three do not give test
9. Ethanol and Methanol are miscible in water
due to LEVEL -I (C.W) - KEY
1) Dissociation of water 2) Their acidic character 1) 2 2) 4 3) 1 4) 2 5) 1 6) 2 7) 4
3) Allyl groups 4) Hydrogen bonding 8) 1 9) 4 10) 4 11) 4 12) 4 13) 4 14) 2
10. To bring about dehydration of alcohols we
can use 15) 2 16) 3 17) 2 18) 2 19) 4 20) 1
1) Conc. H 2 SO4 2) Al2O3 3) ZnO 4) both 1,2 LEVEL -I (C.W) - HINTS
11. The reaction 2 ROH  2 Na  2 RONa  H 2
suggests that alcohols are 1.
1) basic 2) amphoteric
3) neutral 4) acidic 2.  CH 3 3 C  OH
12. Which of the following reaction conditions
are used for the conversion of ethanol to 3. Glu cos e 
Zymase
 ethyl alcohol
ethylene. 4. Lucas reagent is a mixture of
1) conc. H 2 SO4 / 700 C 2) dil. H 2 SO4 /1400 C Conc.HCl  anh ZnCl2
5. Alkyl halides on hydrolysis gives alcohols
3) dil. H 2 SO4 /1000 C 4) conc. H 2 SO4 /1700 C
6. CaO
7. 6  10% C2 H 5OH 7. Absolute alcohol cannot be obtained by simple
fractional distillation because
8. X=3
9. Ethanol and methanol form hydrogen bond with 1) pure C2 H 5OH is unstable
water 2) C2 H 5OH forms chemical bonding with water
10. Conc.H 2 SO4 and Al2O3 are dehydrating agents 3) Oxidation
11. acidic 4) it forms azeotropic mixture with water.
12. 1700 C , con H 2 SO4 8. The number of 10 , 20 and 30 alcoholic groups
13. any one in Mannitoal or Sorbitol are respectively
14. ROH  RCOOH   1) 2, 4 and 0 2) 1, 4 and 0
H
 RCOOR  H 2O
3) 2, 2 and 0 4) 2, 1 and 1
15. C2 H 5OH 9. An isomer of ethanol is
16. C2 H 5OH is 10 - alcohol 1) Methanol 2) Dimethyl ether
3) Diethyl ether 4) Ethyl glycol
17. A  C2 H 4 B  C2 H 5Cl C = C2H5OH 10. Which one of the following is a secondary al-
18. X  CH 3  CH 2  CH 2  OH  C3 H 8O  cohol ?
1) 2 - Methyl - 1 - propanol
Y  CH 3  CH 2  COOH  C3 H 6O2  2) 2 - Methyl - 1 - propanol
19. CH 3CO group is present 3) 2 - Butanol 4) 1 - Butanol
11. If the boiling point of ethanol (molecular
20. X= RCH 2OH ; Y= R2CHOH
weitht = 46) is 780 C , the boiling point of di-
ethyl ether (molecular weight = 74) is
LEVEL-I (H.W)
1) 1000 C 2) 780 C 3) 86 0 C 4) 34 0 C
1. Which of the following is a tertiary alcohol 12. The percentage of C2 H 5OH in wash is
1) Ethyl alcohol 2) Isopropyl alcohol (approximatly)
3) Neopentyl alcohol 4) 2-methyl 2-propanol 1) 95% 2) 10% 3) 50% 4) 75%
2. Glycerol does not contain ........ alcoholic 13. Which of the following alkenes when passed
group
1) 10 2) 20 3) 30 4) 10 and 20 through conc. H 2 SO4 followed by hydrolysis
with boiling water would give tert - butyl
PREPARATION alcohol ?
3. Which of the following enzyme converts 1) Ethylene 2) Isobutylene
maltose to glucose 3) Propylene 4) 1 - Butene
1) Invertase 2) Zymase 3) Maltase 4) Diastase 14. Which one of the following gases is liberated
4. Absolute alcohol is prepared from rectified when ethyl alcohol is heated with methyl
spirit by magnesium iodide ?
1) Steam distillation 2) Fractional distillation 1) Methane 2) Ethane
3) distillation with CaO &Ca 3) Carbondioxide 4) Propane
4) Simple distillation 15. Identify A and B in the following reaction
5. Reaction, CO  2 H 673 k ,300 atm ,/ Cr2O3  zno
2 g   C2 H 5  Cl A
 C2 H 5OH  B
 C2 H 5Cl
may be used for manufacture of : 1) A = aqueous KOH; B = moist Ag2O
1) HCHO 2) CH3COOH 2) A = alcoholic KOH ; B = aqueous NaOH
3) HCOOH 4) CH3OH
3) A = aqueous NaOH ; B = AgNO2
PROPERTIES
6. When wine is exposed to air it become sour 4) A = AgNO2 ; B = KNO2
due to 16. 23g of sodium will react with methanol to give
1) Oxidation of C2H5OH into CH3COOH 1) One mole of oxygen 2) 1/2 Mole of hydrogen
2) Bacteria 3) Virus 4) Formic acid formation 3) One mole of hydrogen 4) 1/4 Mole of oxygen
17. The correct order of decreasing basicity of 14. Methane
the following species is : 15. aq. KOH and AgOH
H 2O, OH  , CH 3OH , CH 3O  16. As per stoichiometry
17. OH   CH 3O   CH 3OH  H 2O
1) CH 3OH  H 2O  OH   CH 3O 
18. More acidic
2) OH   CH 3O   CH 3OH  H 2O 19. Chloroform
3) H2O  CH3OH  CH3O  OH  20. CH 3COOC2 H 5
4) OH   CH 3O   CH 3OH  H 2O
18. Which of the following alcohols is expected to
have the lowest pK a value ?
1) Ethanol 2) 2-Fluoro ethanol
3) 2,2,2-Trifluoroethanol 4) 2-Chloroethanol
19. Action of bleaching powder on ethyl alcohol
gives
1) Chloroform 2) Dichloromethane
3) Trichloroethane 4) Ethylenechloride
20. Which is formed when ethanol reacts with ace-
tic acid
1) CH 3COOC2 H 5 2) C2 H 5OC2 H 5
3) CH 3OCH 3 4) CH 3CH 2CHO
LEVEL -I (H.W) - KEY
1) 4 2) 3 3) 3 4) 3 5) 4 6) 1 7) 4
8) 1 9) 2 10) 3 11) 4 12) 2 13) 2 14) 1
15) 1 16) 2 17) 2 18) 3 19) 1 20) 1

LEVEL -I (H.W) - HINTS

1.  CH 3 3 C  OH
CH 2 OH
|
H-C-OH
2. |
is glycerol
CH 2 OH

3. Maltose  Maltase

 glu cos e
Rectified spirit CaO  Ca
4.  absolute alcohol.
5. Industrial preparation
6. Oxidation
7. azeotropic mixture.
8. On the basis of structure
9. Alcohols and ethers containing the same number of
carbon atoms are functional isomers
10. -OH group is on the secondary carbon
11. b.p of alcohol is greaterthan ether
12. ‘Wash’ contains about 10% ethyl alcohol
13. Isobutylene
 2. ALCOHOLS, PHENOLS & ETHERS
10. Which of the following on oxidation gives
ALCOHOLS ketone
1) CH3—CH2—CH2—OH
LEVEL-II (C.W)
2) CH3—CH2—OH

NOMENCLATURE 3) CH3—CH2—CH2—CH2—OH
1. Which one of the following pairs of 4) CH 3  CH  CH 2  OH
compounds are functional isomers of each |
OH
other
1) CH 3CH 2CH 2OH , CH 3CHOHCH 3 11. Compound A reacts with Na metal to give B.
A also reacts with PCl5 to give C. B and C
2) CH 3CH 2CH 2OH ,  CH 3 2 CHCH 2OH reacts with each other to give dimethyl ether.
3) CH 3CH 2 CH 2 OH , CH 3CH 2 CH 2 Cl Then A, B and C respectively are
4) CH 3CH 2CH 2OH , CH 3OCH 2CH 3 1) CH3OH, CH3ONa, CH3COCl
2) CH3OH, CH4, CH3Cl
2. Primary alcoholic group is
3) CH3OH, CH3ONa, CH3Cl
4) CH3Cl, CH4, CH3OH
1) -CH2OH 2)  C  OH 3) >CHOH 4) >C=O 12. Two organic compounds A and B react with
sodium metal and release H2 gas. A and B
PREPARATION react with each other to give ethyl acetate.
3. Ethyl alcohol containing 9.5% methyl alcohol The A and B are
and 0.5% pyridine is called 1) CH3COOH and C2H5OH
1) Spirit 2) Denaturated spirit 2) HCOOH and C2H5OH
3) Rectified spirit 4) Absolute alcohol 2) CH3COOH and CH3OH
4. Breaking of big organic molecules in the 4) CH3COOH and HCOOH
presence of enzymes is called
13. Which one of the following reagents is useful
1) Cracking 2) Pyrolysis
in converting 1-butanol to 1-bromobutane?
3) Fermentation 4) Oxidation
1) CHBr3 2) Br2 3) CH3Br 4) PBr3
PROPERTIES 14. Which of the following are the starting
5. Which alcohol is most reactive towards materials for the Grignard’s synthesis of
HCl in the presence of anhydrous ZnCl2 ? t-butanol?
1) primary 2) secondary 3) tertiary 4) all of these 1) CH3MgBr + CH3COCH3
6. Isopropyl alcohol on oxidation forms 2) CH3CH2MgBr + CH3COCH3
1) Ethylene 2) Acetone 3) CH3MgBr + CH3CHOHCH3
3) Ether 4) Acetaldehyde 4) CH3MgBr + (CH3)3CH
7. When tertiary butyl alcohol is passed over 15. Ethanol when reacted with PCl5 gave A,
reduced copper, the reaction taking place is
POCl3 and HCl . A reacts with silver nitrate
1) oxidation 2) reduction
3) dehydration 4) substitution to form B (major product) and AgCl . A and
8. When ethylalcohol reacts with Br2 in presence B are respectively
of red phosphorus the compound formed is 1) C2 H 5Cl , C2 H 5OC2 H 5 2) C2 H 6 , C2 H 5OC2 H 5
1) C2H6 2) PBr3 3) CH3Br 4) C2H5Br 3) C2 H 5Cl , C2 H 5ONO 4) C2 H 6 , C2 H 5ONO
9. Ethyl alcohol forms X CaCl 2. C2H5OH; Y 16. The order of reactivity of alcohols towards Na
MgCl 2. C2H 5OH and Z CuSO 4. C2H 5OH or K metal is
when C 2 H 5 OH reacts with respective 1. Primary > Secondary > Tertiary
anhydrous salts. Then 2. Primary < Secondary < Tertiary
1) X =3, Y = 3, Z = 2 2) X =3, Y = 6, Z = 3 3. Primary < Secondary > Tertiary
3) X =3, Y = 7, Z = 4 4) X = 4, Y = 4, Z = 4 4. Primary > Secondary < Tertiary
17. The order of reactivity of dehydration of
alcohol is 7.
1. 10  20  30 2. 10  20  30
P 
3. 10  20  30 4. 10  20  30 8. C2 H 5OH  Br2 
4 n
 C2 H 5 Br  HBr
18. The dehydration of 1-butanol gives 9. Addition reactions of C2 H 5OH
1. 1-butene as the main product
2. 2-butene as the main product 10. 20  or  30 alcohols on oxidation give ketone
3. equal amounts of 1-butene and 2-butene
11. A  CH3OH, B  CH3ONa, C  CH3Cl
4. 2- methylpropene
19. In the esterification reaction, the correct 12. A  CH 3COOH , B  C2 H 5OH
order of reactivity of alcohols is 13. Alcohols are converted into haloalkanes with
1. CH 3OH  CH 3CH 2OH   CH 3 2 CHOH Phophorous trihalides
14. Methyl magnesim bromide and acetone
2. CH 3OH   CH 3 2 CHOH  CH 3CH 2OH 15. A  C2 H 5Cl , B  C2 H 5ONO
3. CH 3CH 2OH   CH 3 2 CHOH  CH 3OH 16. The reactivity of alcohols with active metals is
30  20  10
4.  CH 3 2 CHOH  CH 3OH 2OH  CH 3OH
17. The correct decreasing order of dehydration of
20. The alcohol which gives the most stable
the given alcohols with acids like conc. H 2 SO4
carbonium ion on dehydration is:
1) (CH3)2 CHCH2OH 2) (CH3)3 C - OH is 30  20  10
3) CH3 CH2CH2 CH2 OH 4) CH3-CH-CH2CH3 18. The reaction occur with rearrangement as
21. Which of the following reactions will yield 20 carbocation is more stable than 10 carbo
propan-2-ol? cation.

1) CH  CH  CH  HOH  H 19. Correct order or reactivity is
2 3

2) CH 3  CHO 
CH MgBr / HOH
3
CH 3OH  CH 3CH 2OH   CH 3 2 CHOH
20. 30 carbonium ion more stable
3) CH 2O 
C 2 H 5 MgI / HOH

21. Acetaldehyde on reaction with Grignard reagent

Neutral KMnO4
4) CH 2  CH  CH 3   to give a secondary alcohol

LEVEL -II (C.W) - KEY

1) 4 2) 1 3) 2 4) 3 5) 3 6) 2 7) 3
8) 4 9) 2 10) 4 11) 3 12) 1 13) 4 14) 1 1. 2-Methylpentanol-1 is a
15) 3 16) 1 17) 4 18) 2 19) 1 20) 2 21) 2 1) 10 alcohol 2) 20 alcohol
0
3) 3 alcohol 4) enol
LEVEL -II (C.W) - HINTS 2. Primary alcohol cannot be prepared by the
1. Alcohols and ethers are functional isomers reduction of
whose MF is same 1) aldehyde 2) acid 3) ketone 4) ester
3. The two enzymes present in yeast that are
2. CH 2OH responsible for the formation of ethylalcohol
3. Denaturated spirit from molasses in the fermentation process are
4. Fermentation 1) Invertase, zymase 2) Invertase, diastase
5. Order of reactivity of alcohols towards Lucas 3) Zymase, diastase 4) Invertase, maltase
reagent is 30  20  10 4. An organic compound ‘A’ containing C,H and
O has a pleasant odour with boiling point 780C.
6. On boiling ‘A’ with conc H2SO4,a colourless
gas is released. The organic liquid ‘A’ is:
 1) C2H5 Cl 2) C2H5 COOCH3 4) Secondary > Primary > Tertiary
3) C2H5OH 4) C2H6 14. Match the following lists
5. When equal weights of methyl alcohol and List - I List - II
ethyl alcohol react with excess of sodium A) Ethlene 1) Natalite
B) Acetylene 2) Preservative
metal, the volume of H 2 liberated is more in
C) Ethanol 3) Hawker’s lamp
the case of D) Diethyl ether 4) Drug
1) C2 H 5OH 2) CH 3OH 5) Polyethylene
Correct match is :
3) Equal in both 4) H 2 is not liberated
A B C D A B C D
6. Which one of the following gases is liberated 1) 3 2 1 5 2) 5 1 2 3
when ethyl alcohol is heated with methyl 3) 5 3 2 1 4) 5 1 4 2
magnesium iodide ? 15. 3 moles of ethanol react with one mole of
1) Methane 2) Ethane phosphorous tribromide to form 3 moles of
3) Carbondioxide 4) Propane bromo ethane and one mole of X. Which of
7. Which one of the following alcohols is the following is “X”
expected to have the lowest P Ka value ? 1) H 3 PO4 2) H 3 PO2 3) HPO3 4) H 3 PO3
1) Ethanol 2) 2-Fluoro ethanol
16. Which of the following is most suitable
3) 2,2,2-Trifluoroethanol 4) 2-Chloroethanol.
method for removing the traces of water from
8. R  OH  HX  R  X  H 2O . ethanol ?
In this reaction, the reactivity of alcohols is 1) Heating with Na metal
1) Tertiary > Secondary > Primary 2) Passing dry HCl through it
2) Tertiary < Secondary < Primary 3) Distilling it with CaO 4) Reacting with Mg
3) Tertiary > Primary > Secondary 17. Which of the following compound gives
4) Secondary > Primary > Tertiary ethylmethyl ketone on oxidation ?
9. (CH ) CHOH  1) Propan -2-ol 2) Butan -1-ol
3 2
mild oxidation
 X 
(i ) CH3MgBr
H2O
Y 3) Butan - 2-ol 4) 2-methylbutan-2-ol
Here ‘Y’ is
18. In CH 3CH 2OH , the bond that undergoes het-
1) Iso butyl alcohol 2) Iso butylene
3) sec.Butyl alcohol 4) tert.Butyl alcohol erolytic cleavage most readily in reaction with
10. Haloform reaction is not given by ‘Na’ is
1) C  C 2) O  H 3) C  H 4) C  O
1) CH 3COCH 3 2) CH 3COC2 H 5
19. What are X and Y in the reaction
3) C6 H 5COC2 H 5 4) CH 3CHOHCH 3 H 2O / 
C2 H 4  H 2 SO4 800 C
 X  Y
11. What is the final product obtained when chlo-
rine LEVEL-II
reacts with ethyl
(H.W) alcohol in KOH? 1) C2 H 6 , C2 H 5OH 2) C2 H 2 , C2 H 5 SH
1) CHCl3 2) CCl3CHO 3) CH 3Cl 4) none 3) C2 H 5OSO3 H , C2 H 5OH 4) C2 H2 , CH3CHO

12. C2 H 5OH 
KMnO4 / H
X  Y
 20. Which one of the following contains
H 2 SO4
CSP 2  OH bond ?
CH 3COOC2 H 5 , X and Y respectively aree
1) vinyl alcohol 2) allyl alcohol
1) CH 3OH ; C2 H 5OH 2) CH 3CHO; CH 3OH 3) benzyl alcohol 4) carbolic acid
3) CH 2  CH 2 ; CH 3COOH 4) CH 3COOH ; C2 H 5OH LEVEL -II (H.W) - KEY
13. R  OH  HX  R  X  H 2O . In this reac- 1) 1 2) 3 3) 1 4) 3 5) 2 6) 1 7) 3
tion, the reactivity of alcohols is 8) 1 9) 4 10) 3 11) 1 12) 4 13) 1 14) 3
1) Tertiary > Secondary > Primary
15) 4 16) 3 17) 3 18) 2 19) 3 20) 1
2) Tertiary < Secondary < Primary
3) Tertiary > Primary > Secondary
 LEVEL -II (H.W) - KEY OH OH
1. Primary alcohol
2. Ketone 1) Na2Cr2O7 / H 2 SO4 2) Zn
3. Invertase, Zymase
4. Primary alcohol does not give turbidity (X) (Y) (X) (Y)
immediately with Lucas reagent.
5. Methyl alcohol
OH OH
6. CH 4
7. More acidic 3. Zn 4) Na2Cr2O7 / H 2 SO4
8. 3  2 1
0 0 0

9. tert. butyl alcohol (X) (Y) (X) (Y)

O

10. does not contain || group PREVIOUS EAMCET - KEY : 1) 2 2) 4

C  CH 3
11. Chloroform
12. CH 3COOH ; C2 H 5OH
NOMENCLATURE
13. Tertiary > Secondary > Primary
1. C

2
OH—CHOH—CH2OH is glycerol.
H

15. H 3 PO3 It doesn't contain ------------ alcoholic group

16. Distillation 1) 10 2) 20 3) 30 4) both 10 & 20
17. 2-Butanol 2. An example for a polyhydric alcohol is
18. O-H 1) Methyl alcohol 2) Neopentyl alcohol
19. C2 H 5OSO3 H , C2 H 5OH 3) Sec butyl alcohol 4) Mannitol
20. tert-butyl alcohol 3. Which one of the following is a secondary
alcohol
PREVIOUS EAMCET QUESTIONS 1) 2-methyl-2-propanol 2) 1-propanol
1. Identify the product in the following reaction 3) 1-butanol 4) 2-pentanol
OH PREPARATION
4. Ethyl alcohol is manufactured from ethylene
CHCl3 by
  Product 1) Permanganate 2) Catalytic oxidation
NaOH
3) Absorption into Conc. H2SO4 followed by
CHO OH hydrolysis 4) Reduction
CHO 5. Which of the following pairs of the compounds
can be used as starting materials in the synthesis
1) 2) of 2-phenyl-2-pentanol?
1) CH 3  CH 2 3 Br and PhCOOH
OH CO2H 2)  CH 3 2 CHCH 2 Br and PhCOCH 3
CO2H
3) PhBr and CH 3CH 2CH 2COCH 3
3) 4) 4) PhBr and  CH 3 2 CHCH 2COCH 3
6. An enzyme which brings about the
2. X Y
 Benzoquinone . Identify X and Y in conversion of starch into maltose is known
as
this reaction
1) Diastase 2) Zymase 3) Maltase 4) Invertase
7. Which is the catalyst in the conversion of water
gas and hydrogen into methyl alcohol?
1) MnO 2) raney Ni 3) Fe 4) ZnO-Cr2O3
 PROPERTIES ethyl chloride is formed. Mole ratio of PCl3
8. When ethyl alcohol is distilled with bleaching and PCl5 in the mixture is
powder and water then chloroform is
1) 3 :1 2) 1:1 3) 1: 3 4) 2 :1
obtained. The no. of moles of bleaching
powder needed in the preparation of one mole 17. When vapours of an alcohol are passed over
hot reduced copper, it gives an alkene. The
of chloroform is
alcohol is
1) 10 2) 5 3) 4 4) 2
1) Primary 2) Secondary
9. CH3OH + PCl3  A
3) Tertiary 4) None of these
A 
KCN
 B  
hydrolysis
 C .Then "C" is 18. When ethylhydrogen sulphate is heated with
1) CH3CH2OH 2) CH3CHO excess of alcohol at 410K, the product obtained
3) CH3COOH 4) CH2OH-CH2OH is
10. An organic liquid A containing H and O has 1) Ethane 2) Ethylene
a pleasant odour with a boling point of 780C. 3) Diethyl ether 4) Diethyl sulphate
On boiling A with conc. H2SO4 a colourless 19. How many primary alcoholic isomers are
gas is produced which decolourises bromine possibe for C5 H11OH ?
water and alkaline KMnO4. One mole of this
1) 5 2) 4 3) 2 4) 3
gas also takes one mole of H2. The organic 20. Methanol is industrially prepared by
LEVEL-III
liquid A is
1) C2H5Cl 2) C2H5CHO 3) C2H6 4) C2H5OH 1) Oxidation of CH 4 by steam at 900 0 C
11. A compound reacts with sodium and liberates 2) Reduction of HCHO using LiAlH 4
hydrogen and on oxidation gives ketone. The 3) Reaction HCHO with a solution of NaOH
formula of the compound could be.
1) CH3CH2OH 2) CH3CHOHCH3 4) Reduction of CO using H 2 and ZnO  Cr2O3
3)CH3CH2CH2OH 4) CH3CH2 CH2CH2OH 21.  CH 3 3 C  OH 
H SO
2
  CH 3 2 C  CH 2 ;
4

12. Iodoform cannot be prepared from This reaction takes place through
1) CH 3OH 2) C2 H 5OH 1) S N 1 mechanism 2) S N 2 mechanism
3) CH 3CHO 4) CH 3COCH 3 3) E1 mechanism 4) E2 mechanism
13. I2 produced when ozone reacts with moist KI
is used to convert C 2H 5OH to CI 3CHO. LEVEL-III - KEY
Number of moles of ozone required to convert 1) 3 2) 4 3) 4 4) 3 5) 3 6) 1 7) 4
1 mole of C2H5OH into CI3CHO is 8) 3 9) 3 10) 4 11) 2 12) 1 13) 3 14) 2
1) 1 2) 2 3) 4 4) 3 15) 1 16) 2 17) 3 18) 3 19) 2 20) 4 21) 3
14. A compound "X" of the formula C3H8O gives
iodoform test. On oxidation with acidified LEVEL-III - HINTS
K2Cr2O7, X gave Y. Y also gives iodoform 1. HO  CH 2  CH  OH   CH 2  OH is glycerol.
test. Then X and Y are
2. Mannitol is hexahydric alcohol
1) CH3CH2CH2OH, CH3CH2CHO
3. 2-pentanol
2) CH3CHOHCH3 ,CH3COCH3
4. It is an industrial method of preparation of ethyl
3) CH3CH2CHO, CH3CH2CH2OH alcohol.
4) CH3COCH3, CH3CHOHCH3 5. Bromobenzene
15. In the Victor-Meyer’s test, red colouration is 6. Diastase
shown by ZnO Cr2O3
7. CO  H 2   CH 3OH
1) 10 Alcohol 2) 20 Alcohol
8. Four moles of bleaching power needed in the
3) 30 Alcohol 4) Phenol prepration of one mole of chloroform
16. When a mixture containing PCl3 and PCl5 is
heated with ethyl alcohol, a total of 4 moles of
 5. Assertion (A): Ethyl alcohol is soluble in
9. CH 3OH 
PCl3
 CH 3Cl organic solvents
 A
Reason (R) : Ethyl alcohol is having non polar

 CH 3CN 
KCN H 2O
 CH 3COOH
 B C  ethyl group.
6. Assertion (A): The boiling point of C2H5OH
10. C2 H 4 decolourises bromine water and alkaline is less than that of H2O though the molecular
KMnO4 weight of C2H5OH is more than that of water.
11. 20  or  30 alcohols on oxidation give ketone
Reason (R) : C 2H 5OH molecules are not
highly associated through hydrogen bonding
12. group gives iodoform test as water is
7. Assertion (A): Dehydration of alcohols can be
13. C2 H 5OH  4 I 2  CI 3CHO  5HI carried out with Conc H2SO4 but not with
4( O3  2 KI  H 2 O  2 KOH  I 2  O2 ) conc.HCl.
14. X= secondary alcohol ; Y= ketone Reason (R) : H2SO4 is dibasic while HCl is
15. Primary alcohol monobasic.
16. 1:1
8. Hydroboration-Oxidation of CH 3CH  CH 2
17. Tertiary alcohol undergoes dehydration
18. Diethyl ether produces.
19. based on the structure 1. CH 3CH 2CH 2OH 2. CH 3CH  OH  CH 3
20. from CO and H2
21. E1 mechanism 3. CH 3CH  OH  CH 2OH 4. CH 3COCH 3
9. The compound which gives the most stable
LEVEL-IV
carbonium ion on dehydration.
1) Both A and R are true and R is the correct CH3
explanation to A CH 3 CH CH2OH CH
2) Both A and R are true and R is not the correct 1) 2) 3 C OH
explanation to A CH 3 CH3
3) A is true but R is false CH3 CH CH2CH3
4) A is false but R is true 3) CH 3CH 2CH 2CH 2OH 4)
1. Assertion (A): In the fermentation process of OH
molasses, along with yeast (NH 4 ) 2SO 4 , 10. An alcohol on oxidation gives CH 3COOH and
(NH4)3PO4 is added.
CH 3CH 2COOH . The alcohol is
Reason(R): (NH4)3PO4 and (NH4)2SO4, act as
food and helps the growth of yeast. 1. CH 3CH 2OH
2. Assertion (A): Alcoholic fermentation
involves conversion of sugar into ethanol by 2. CH 3CH  OH  CH 2CH 3
the action of yeast.
3.  CH 3 2 C  OH  CH 2CH 3
Reason(R): Fermentation involves the
liberation of CO2 gas. 4. CH 3CH  OH  CH 2CH 2CH 3
3. Assertion (A): Ethanol is miscible in all
11. An alcohol (A) on heating with concentarated
proportions with water
Reason (R) : Hydrogen bond is formed H 2 SO4 gives alkene (B) which can show the
between water and alcohol molecules. geometrical isomerism. The compound(A) is:
4. Assertion (A): CaCl2 can’t be used for drying 1) (CH3)2 C (OH) CH (CH3)2
ethyl alcohol 2) (CH3)2 C (OH) CH2 Me
Reason (R) : Calcium chloride can form an 3) CH3 CH2 CH (OH) CH3
addition compound with ethyl alcohol 4) All of the above
12. Which of the following compounds on reaction PREVIOUS MAINS QUESTIONS
with CH3 Mg Br Will give a teritiary alcohol? 1. Arrange the following compounds in order of
1) C2H5 CHO 2) HCHO decreasing acidity
3) C2H5 COOH 4) C2H5 COOCH3
13. 0.037g of an alcohol R-OH was added to OH OH OH OH
CH3MgBr and the gas evolved measured
11.2ml at STP.The molecular mass of
R--OH will be
1) 47 2) 79 3) 74 4) 77
Cl CH3 OCH3
LEVEL-IV - KEY
1) 1 2) 2 3) 1 4) 1 5) 1 6) 1 7) 2 (1) (2) (3) (4)

8) 1 9) 2 10) 4 11) 3 12) 4 13) 3 1) II > IV > I > III 2) I > II > III > IV
3) III > I > II > IV 4) IV > III > I > II
LEVEL-IV - HINTS
1. Ammonium phosphate and ammonium sulphate PREVIOUS MAINS KEY : 1) 3
act as food for yeast
2. Both are correct ADDITIONAL QUESTIONS
3. Ethanol is a associated with water through 1. What is the structure of  C4 H10O  which can
hydrogen bond. give positive haloform test and evolves
4. CaCl2 3C2 H 5OH hydrogen gas with LiAlH 4 .
5. Ethyl alcohol is soluble in polar and non polar
1) CH 3  CH 2  O  CH 2  CH 3
solvents.
6. Both are correct CH 3
7. with HCl R-Cl will form
8. 3CH 3CH  CH 2 
BH inTHF3
  CH 3CH 2CH 2 3 B 2)
CH 3  CH  CH 2  OH
  CH 3CH 2 CH 2 OH  H 3 BO3
3 H 2 O2
OH 
CH 3
9. 3 carbanium ion is most stable.
0

CH 3  CH  CH 2  CH 3
CH 3CH  OH  CH 2CH 2CH 3 
  CH 3  C  OH
O

10. 3) 4)
CH 3COOH  CH 3CH 2COOH OH
CH 3
11. A  CH 3CH 2CH  OH  CH 3 2. The relative rates of reaction with
B  CH 3CH  CHCH 3 concentrated H 2 SO4 of the following is
O I)
OH
|| OH OH
12.
CH 3  CH 2  C  OCH 3 
CH 3 MgBr
excess
?
II) III)
13. 11.2 ml of CH 4 at STP is formed by 0.037 g of
R-OH
1) I > II > III 2) II > I > III
22.400 ml CH 4 at STP .......? 3) I > III > II 4) II > III > I
0.037  22, 400 3. Which of the following is the best dehydrating
= = 74g of alcohol agent for 10 alcohols
11.2
1) Con H 2 SO4 2) CaO 3) Al2O3 4) POCl3
 CH3 CH3
OH
Con
NBS Ph C C Ph Product is

 8. H2SO4
4.
OH OH
Ph
Product (A) is Ph C C Ph
Ph C C CH3
OH O  Br 1) 2)
O O
O CH3
1) 2)
CH 3  CH  CH 2  Br CH 3  CH  CH 3 Ph
Ph C C CH3
O CH3 C C CH3
3) 4)
3) 4) CH 3  CH 2  CH 3 O Ph
O O
CH 3  C  CH 3
9. Which of the following alcohols is the least
5. What is the major of the following reaction? soluble in water?
O 1) Ethanol 2) 1-Propanol 3) 1-Butanol 4) 1-Pentanol
10. 3, 3-Dimethyl-2-butanol on reaction with
NaBH
HCl yields mainly

4  Products is
1) 2-Chloro-2, 3-dimethylbutane
2) 1-Chloro-2, 3-dimethylbutane
3) 2-Chloro-3, 3-dimethylbutane
OH OH 4) 1-Chloro-3, 3-dimethylbutane
11. Propylene is subjected to hydroboration
oxidation reaction. The product formed
would be
1) 2) 1)Propanal 2)1-Propanol 3)2-Propanol 4)Propanone
12. Ethylene glycol when heated in the presence
CO2H CO2H
of an hydrous ZnCl2 yields.
O O
1) Ethanal 2) Ethylene oxide
3) Dioxane 4) Diethylene glycol
13. Clear orange solution of chromic anhydride
3) 4) in aqueous sulphuric acid turn blue-green on
reaction with
1) 3-Methyl-3-pentanol 2) 2-Butanol
6. Which are not cleaved by HIO4 ? 3) 2-Methyl-2-propanol 4) 2-Methyl-2-butanol
I) glycerol II) glycol 14. An organic compound ‘X; on treatment with
III)1, 3-propenediol acidified K 2Cr2O7 gives a compound ‘Y’ which
IV)methoxy-2-propanol reacts with I 2 and sodium carbonate to form
1) I, II, III, IV 2) I, II
3) II, III 4) III, IV triodomethane. The compound ‘X’ could be
CH3 1) CH 3OH 2) CH 3CHO
NA2Cr2O7 3) CH 3CH  OH  CH 3 4) CH 3COCH 3
7. CH3 C CH3 ? 15. Fusel oil is a mixture of
Cool
OH
1) Ethers 2) alcohols
3) Alcohols and ethers 4) Alcohols and ketones
CH3 CH3 16. How many structuaral isomeric compounds
1) 2) are possible for C4 H10O ?
CH3 C CH2 CH3 CH CH3 1) 4 2) 5 3) 6 4) 7
CH3 CH3 i CH3Mgl
17.   X 
Cu /575 K
Y
ii H2O

3) CH 2 C O C CH3
4) No reaction The compound Y in the above sequence is
CH3 CH3 1) 2-Methyl-2-phenyl-1-propanol
 2) 2-Phenyl-2-propanol 3) Acetophenone 25. Rate of hydration of
4) 2-Methyl-1-phenyl-2-propanol
18. Which is the best reagent to convert isopropyl I) CH = CH2 II) CH = CHCH3
alcohol to isopropyl bromide?
CH 3 CH 3
III) CH = CH2
CH 3  CH  OH 
?
 CH 3  CH  Br
will be in order;
1) HBr 2) SOBr2 3) Br2 4) CH 3 MgBr 1) I<II<III 2) I<III<II 3) II<I<III 4) III<II<I
19. Choose the alcohol that is most reactive with 26. Glycerol

KHSO4
 A LiAlH 4
 B , A and B
conc. HCl / ZnCl2 ? are;
1) Methanol 2) Ethanol 1) Acrolein, allyl alcohol
3) 2-propanol 4) 2-methyl-2-propanol 2) Glyceryl sulphate, acrylic acid
20. Treatment of 3-methyl-2-butanol with 3) Allyl alcohol, acrolein
dry HCl gives 4) Only acrolein (B is not formed)
OH OH
27. 2 5 . In this dioal
Cl
1) 2)
Cl
1) OH at C2 is more basic than that of at C5
2) OH at C2 is more acidic than at C5 .
3) 4)
Cl 3) both have same basic strength
21. Glycol on treatment with PI 3 mainly gives 4) both have same acidic strength
28. Lucas test is used to make distinction between
1) Ethylene 2) Ethylene iodide
3) Ethyl iodide 4) Ethane 10 , 20 and 30 alcohols. This do not show that
22. Acrolein is formed when glycerol is heated 1) ROH behaves as a base
with 2) greater the value of pK a (alcohol), greater
1) Acidified KMnO4 2) Br2 water the reactivity with conce. HCl and thus sooner
3) KHSO4 4) HNO3 the formation of white turbidity.
3) alcohol which reacts fastest with Na metal,
23. Glycerol on treatment with oxalic acid at will give turbidity at fastest rate
1100 C forms 4) alcohol which gives red colour during Victor
1) Allyl alcohol 2) Formic acid Mayor test, will give turbidity ast slower rate
3) CO2 and CO 4) Glyceric acid then those giving blue or white colour during
24. If the starting material is 1-methyl-1, Victor Mayor test.
2-epoxy cyclopentane, of absolute 29. Match the column:
configuration, decide which one compound Column -I Column - II
correctly represent the product of its reaction A) Oxidation of 10
with sodium methoxide in methanol. alcohols in aldehyde P) KMnO4 / 

CrO3. .HCl
1) 2) B) Q) Collin’s reagent
OCH3 CH3O CH3
HO CH3 OH N

CrO3.2
3) CH3 4) C) R) Jone’s reagent
OH
CH3O CH3O CH3
N
 D) Oxidation of alkene into acid
S) P.C.C
CH 3  CH  CH  CH 2 
Reagent R
 Alcohol
30.
CH 3
Which is true about alcohol and R?
Alcohol Reagent
C H 3  C H  C H 2  C H 2O H

A) B2 H 6 , H 2O2 / NaOH
CH 3
CH 3  CH  CH  CH 3

B) PdCl2 , H 2O, O2 / LAH

CH 3 OH

OH

C H 3  C  C H 2C H 3
C) Hg  OAc 2 , H 2O / NaBH 4
CH 3
OH

C H 3  C  C H 2C H 3
D) dil. H 2 SO4
CH 3

ADDITIONAL QUESTIONS - KEY

1) 3 2) 4 3) 4 4) 3 5) 1 6) 4 7) 4
8) 3 9) 4 10) 1 11) 1 12) 4 13) 2 14) 3
15) 2 16) 4 17) 3 18) 2 19) 4 20) 2 21) 1
22) 3 23) 2 24) 2 25) 1 26) 1 27) 1
28) 1, 2, 4
29) (A) Q, R, S (B) S (C) Q (D) P 30) A, B, D
ADDITIONAL QUESTIONS - HINTS
1. 2-hydroxy-2-alcohols responds to haloform
reaction
2. Stability of alkene in driving force
3. POCl2 is better leaving group
4. NBS is oxidising agent
5. H  attack on can less hindered side
6. 1,2 diols oxidised by HIO4
7. 30 alcohols do not undergoes oxidation
9. as the Bulkyness increases solubility decreases
10. 1, 2 alkyl shift
11. anti markoniv’s addition of H 2O
13. 10 and 20 alcohols oxidised by K 2Cr2O7 / H 