WorksheetsALCHOLS,PHENOLS & ETHERS
Total questions: 100
Worksheet time: 50mins
1. In Allylic and benzylic alcohols,-OH group is attached to
sp2 hybridised carbon atom respectively
sp2 sp hybridised carbon atom respectively
sp3 hybridised carbon atom respectively
sp sp2 hybridised carbon atom respectively
Which of the following compounds is a polyhydric alcohol?
C2H4O
C2H6O
C4H10O
C3H8O3
The IUPAC name of
3-methyl hydroxyhexane
2-ethyl-2-propyl ethanol
2-ethylpentan-1-ol
3-propylbutan-1-ol
A compound C6H14O2 has two tertiary alcoholic groups. The IUPAC name of this compound is
3,3-dimethyyl-1,2-butanediol
2methyyl-2,3-pentanediol
2,3-dimethyyl-1,2-butanediol
2,3-dimethyyl-2,3-butanediol
Which of the following is phenol?
benzenol
cresol
catechol
all of these
Match the column I with column II and mark the appropriate choice
(A)(ii),(B)(iv),(C)(i),(D)(iii)
(A)(ii),(B)(iii),(C)(iv),(D)(i)
(A)(i),(B)(ii),(C)(iii),(D)(iv)
(A)(iv),(B)(iii),(C)(ii),(D)(i)
The C-O-C angle in either is about
110°
180°
105°
190°28’
The C-O-H bond angle in alcohols is slightly less than the tetrahedral angle whereas the C-O-C bond angle in ether is slightly greater because
O atom in both alcohols and ethers is sp3 hybridised
lone pair-lone pair repulsion is greater than bond pair-bond pair repulsion
of repulsion between the two bulky R groups
none of these
The best method to prepare 3-methylbutan-2-ol from 3-mryhybut-1-ene is
addition of HCl followed by reaction with dil.NaOH
Retimer-Tiemann reaction
addition of water is presence of dil.H2SO4
hydroboration-oxidation reaction
An alkene CH3CH=CH2 is treated with B2H6 in presence of H2O2. The final product formed is
CH3CH2CH2OH
CH3CH2CHO
CH3CH(OH)CH3
(CH3CH2CH2)3B
Choose the correct X & Y in the given reactions:
Which reducing agent is used for the following conversion?
RCOOH→ RCH2OH
NaBH4
LiAlH4
K2Cr2O7
KMnO4
One mole of ethyl acetate on treatment with an excess of LiAlH4 in dry ether and subsequent acidification produces
1 mol ethyl alcohol + 1 mol methyl alcohol
1 mol acetic acid + 1 mol ethyl alcohol
1 mol of 2-butanol
2 moles of ethyl alcohol
Tertiary butyl alcohol can be prepared by the reaction of
acetone and methyl magnesium iodide
butanone and methyl magnesium iodide
acetaldehyde and ethyl magnesium iodide
formaldehyde and propyl magnesium iodide
1-phenylethanol can be prepared by the reaction of benzaldehyde with
methyl bromide
methyl iodide and magnesium
ethyl iodide and magnesium
methyl bromide and aluminum bromide
What would be the reactant and reagent used to obtain 2,4-dimethylpemtam-3-ol?
2,2- dimethypropanone and methyl magnesium iodide
propanal and propyl magnesium bromide
2-methylpropanal and isopropyl magnesium iodides
3-methylbutanal and 2-methyl magnesium iodide
Propanone on reaction with alkyl magnesium bromide followed by hydrolysis will produce
secondary alcohol
primary alcohol
carboxylic acid
tertiary alcohol
Identify A,B & C
CH3COOH (CH3)2CHOMgBr CH3CH2OH
CH3COCH3 (CH3)3 COMgBr (CH3)3COH
In the following sequence of reactions.
The compound Q formed will be
phenol
aniline
benzene sulphonic acid
benzaldehyde
Cumene on reaction with oxygen followed by hydrolysis gives
C6H5OCH3 & CH3OH
CH3OH & C6H5COCH3
C6H5OH & (CH3)2O
C6H5OH & CH3COCH3
Which of the following reactions will not yield phenol?
The decreasing order of boiling points of the following alcohols is
2-methylbutan-2-ol>pentan-1-ol>3-methylbutan-2-ol
3-methylbutan-2-ol>2-methylbutan-2-ol > pentan-1-ol
3-methylbutan-2-ol>3-methylbutan-2-ol>pentan-1-ol
pentan-1-ol>3-methylbutan-2-ol>2-methylbutan-2-ol
Which of the following statements is not correctly showing the trend of the properties mentioned?
CH3CH2OH >CH3CH2OH>CH3CH2CH2CH2OH
CH3CH2OH< CH3CH2CH2OH <CH3CH2CH2CH2OH
(boiling point)
Which of the following is not a characteristic of alcohol?
their boiling points rise fairly uniformly with rising molecular weight
lower members have a pleasant smell and burning taste, higher members are colourless and tasteless
they are lighter than water
lower members are insoluble in water and organic solvents but the solubility regularly increases with molecular mass
Phenol is heated with a solution of mixture of KBr & KBrO3. The major product obtained in the above reaction is
3-bromophenol
4-bromophenol
2-bromophenol
2,4,6-tribromoophenol
ortho-nitrophenol is less soluble in water than p- and m-nitrophenols because
melting point of o-nitrophenol is lower than those of m- and p-isomers
o-nitrophenol shows intramolecular H-bonding
o-nitrophenol is more volatile in steam than those of m- and p-isomers
o-nitrophenol shows intermolecular H-bonding
Unlike phenol 2,4- dinitrophenol is soluble in sodium carbonate solution in water because
presence of two-NO2 groups make the hydrogen bonding easier, making 2,4-dinitrophenol soluble
presence of two-NO2 groups in the ring makes 2,4-dinitrophenol a stronger acid than phenol
nitrogroup reacts with Na2CO3 while-OH group does not
presence pf two-NO2 groups in the ring makes 2,4-dinitrophenol a weaker acid than phenol
For the reaction, C2H5OH +HX → , C2H5X +H2O the order of reactivity is
HI>HBr>HCl
HBr>HCl>HI
HCl>HBr>HI
HI>HCl>HBr
Which of the following is the proper method to prepare n-hexane from n-propyl alcohol?
X-HBr,Y-Na, ether
X-Br2,Y-KMnO4
X-HBr,Y-HCN
X-Br2,Y-CH3CN
Arrange the following alcohols in order of increasing reactivity towards sodium metal
i) (CH3)3C-OH
ii) (CH3)CH-OH
iii) CH3CH2OH
(i)<(ii)<(iii)
(iii)<(i)<(ii)
(iii)<(ii)<(i)
(i)<(ii)<(iii)
Which of the following compounds does not react with NaOH?
CH3CONH2
CH3CH2OH
CH3COOH
C6H5OH
Out of 2-chloroethanol and ethanol which is more acidic and why?
ethanol due to +I effect of CH3
ethanol due to -I effect of CH3
2-chloroethanol due to +I effect of Cl
2-chloroethanol due to -I effect of Cl
The correct sequence of decreasing acidity is
C2H5OH> CH3OH>(CH3)3COH>(CH3)2CHOH
(CH3)2CHOH>(CH3)3COH> C2H5OH> CH3OH
(CH3)3COH>(CH3)2CHOH>C2H5OH>CH3OH
CH3OH> C2H5OH>(CH3)2CHOH>(CH3)3COH
The correct order of strength of acidity of the following compounds is
(i)>(iii)>(i)>(ii)
(i)>(ii)>(iii)>(iv)
(ii)>(i)>(iii)>(iv)
(iv)>(iii)>(ii)>(i)
P-nitrophenol is a stronger acid than phenol while p-cresol is a weaker acid. This can be explained s
-CH3 group increases the electron density on oxygen of O-H group making the release of H+ easier
-CH3 group decreases the electron density on oxygen of O-H group making p-cresol a weaker acid
-NO2 group increases the electron density on oxygen of O-H group making release of H+ easier
-NO2 group decreases electron density on oxygen of O-H group making p-nitrophenol a stronger acid
Order of esterification of alcohols is
1°>2°>3°
3°>1°>2°
2°>3°>1°
none of these
n-propyl alcohol and iso propyl alcohol can be chemically distinguished by which reagent?
PCl5
K2Cr2O7/H2SO4
H2/Ni
O3/Zn.H2O
Which of the following alcohols reacts most readily with lucas reagent?
CH3CH2CH2OH
Tertiary butyl alcohol gives tertiary butyl chloride in treatment with
KCN
Cl2
conc. HCl/anhydrous ZnCl2
NaOCl
R-OH+HX→RX+H2O
In the above reaction the reactivity of alcohols is
tertiary>secondary>primary
secondary>primary> tertiary
tertiary<secondary<primary
tertiary>primary>secondary
Consider the following reaction sequences,
CH3CH=CHCH3,CH3CH2CH2OH
CH3CH2CH2CH3, CH3CH(OH)CH2CH3
CH3CH=CH2,CH3CH(OH)CH3
CH3CH2CH=CH2,CH3CH2CH2OH
Which of the following alcohols will give the most stable carbocation during dehydration?
2-methyl-1-propanal
1-butanol
2-butanol
2-methyl-2-propanol
In the reaction X is
CH3C≡CH
(CH3)2CHCH2CH3
(CH3)2C=CHCH3
CH3-CH2-C=CH2
|
CH3
Acid catalyst dehydration of t-butanol is faster than that of n-butanol because
t-butanol has a higher boiling point
tertiary carbocation is more stable than primary carbocation
rearrangement takes place during dehydration of t-butanol
primary carbocation is more stable than tertiary carbocation
Dehydration of the following in increasing order is
II<III<IV<I
I<III<IV<II
I<II<III<IV
none of these
An alcohol X when treated with hot conc.H2SO4 gave an alkene Y with formula C4H8. This alkene on ozonolysis gives single product with molecular formula C2H4O. The alcohol is
butan-2-ol
butan-1-ol
2,2-dimethylbutan-1-ol
2-methyl-propan-1-ol
The major product of acid catalysed dehydration of 2-methylcyclohexanol and butan-1-ol are respectively
2-methylcyclohexene and but-2-ene
2-methylcyclohexene and butene
1-methylcyclohexane and but-1-ene
1-methylcyclohexene and but-2-ene
Which of the following alcohols is dehydrated most easily with conc. H2SO4?
p-CH3CC6H4CH(OH)CH3
p-ClC6H4CH(OH)CH3
C6H5CH(OH)CH3
p-O2NC6H4CH(OH)CH3
In the following reactions
the major products A & C are respectively
An alcohol X on heating with concentrated H2SO4 gives an alkene Y which can show geometrical isomerism. The alcohol X is
(CH3)3C(OH)
(CH3)2C(OH)CH(CH3)2
(CH3)2C(OH)CH2CH3
CH3CH2CH(OH)H3
A compound X with the molecular formula C3H8O can be oxidized to another compound Y whose molecular formula C3H6O2. The compound X may be
CH3CH2OCH3
CH3CH2CH2CHO
CH3CHOHCH3
CH3CH2CHO
The best reagent to convert pent-3-en-2-ol into pent-3-en-2-one is
acidic dichromate
pyridinium chlorochromate
chromic anhydride in glacial acetic acid
acidic permanganate
The most suitable reagent for the conversion of RCH2OH→ RCHO is
CrO3
PCC
K2Cr2O7
KMnO4
In the following reaction sequence, Z is
butan-2-ol
1,1-dimethylethanol
2-methylpropan-2-ol
butan-1-ol
Conversion of ethyl alcohol into acetaldehyde is an e.g. Of
oxidation
molecular rearrangement
hydrolysis
reduction
Vapour of an alcohol X when passed over hot reduced copper produce an akene, the alcohol is
secondary alcohol
tertiary alcohol
primary alcohol
dihydric alcohol
Which of the following is not true in case of reaction with heated copper at 300℃?
primary alcohol→aldehyde
Secondary alcohol→ketone
tertiary alcohol→olefin
phenol→benzyl alcohol
What happens when tertiary butyl alcohol is passed over heated copper at 300℃?
1-butene is formed
secondary butyl alcohol is formed
2-methylpropene is formed
butanal is formed
Which of the following reagents cannot be used to oxidise primary alcohols to aldehydes?
KMnO4 in acidic medium
CrO3 in anhydrous medium
heat in the presence of Cu at 573K.
Pyridinium chlorochromate
Which of the following compounds will be most easily attacked by an electrophile?
Conversion of phenol to salicylic acid and to salicylaldehyde is known as (respectively)
Williamson’s synthesis & hydroboration-oxidation
Kolbe’s reaction and Williamson’s synthesis
Reimer-Tiemann reaction & Kolbe’s reaction
Kolbe’s reaction& Reimer-Tiemann reaction
Picric acid is a yellow coloured compound. It is chemical name is
2,4,6-trinitrophenol
p-nitrophenol
m-nitrobenzoic acid
2,4,6-tribromophenol
Phenol when treated with excess of bromine water gives a white precipitate of
p-bromophenol
2,4,6-tribromophenol
bromobenzene
o-bromophenol
Which of the following compounds will give tribromo derivative on treatment with bromine water?
The major product obtained on interaction of phenol with sodium hydroxide and carbon dioxide is
salicylaldehyde
phthalic acid
benzoic acid
salicylic acid
The reaction between phenol & chloroform in the presence of aqueous NaOH is
electrophilic substitution reaction
nuclephilic substitution reaction
nucleophilic addition reaction
electrophilic addition reaction
Out of benzene and phenol, phenol is more easily nitrated because
presence of -OH group in phenol decreases the electron density at ortho and para-position
phenol is more reactive than benzene due to -R effect
presence of -OH group in phenol increases the electron density at ortho and para-position
nitration being electrophilic substitution requires less density at ortho and para-position
In the given reactions, X & Y are respectively,
p-bromophenol and salicylaldehyde
bromobenzene & acetophenone
o & p-bromophenol& salicylaldehyde
o-bromophenol & benzoic acid
Identify the final product of the reaction sequence
diphenyl
methyl salicylate
benzophenone
acetophenone
Benzoquinone is prepared by reaction of phenol with
KMnO4, H2SO4
K2MnO4, H2SO4
Na2Cr2O7, H2SO4
Na2CrO4, HCl
Which of the following statements is correct?
tertiary alcohol is more acidic than primary alcohol
the reaction of methyl magnesium iodide with acetone followed by hydrolysis gives secondary butanol
tertiary butyl alcohol gives turbidity fastest with lucas reagent
primary alcohols are dehydrated easily than secondary and tertiary alcohols
P-cresol reacts with chloroform in alkaine medium to give the compound A which adds hydrogen cyanide to form the compound B. The latter on acidic hydrolysis gives chiral carboxylic acid. The structure of the carboxylic acid is
A primary alcohol, C3H8O(A)on heating with sulphuric acid undergo dehydration to give an alkene B.B when reacted with HCl gave C, which on treatment with aqueous KOH gives compound D(C3H8O) A & D are
chain isomers
position isomers
functional isomers
stereoisomers
Match the column I with column II and mark the appropriate choice.
(A)(ii),(B)(iii),(C)(iv),(D)(i)
(A)(iii),(B)(iv),(C)(i),(D)(ii)
(A)(i),(B)(iii),(C)(ii),(D)(iv)
(A)(iv),(B)(i),(C)(ii),(D)(iii)
Consider the following reaction
The product Z is
benzoic acid
toluene
benzaldehyde
benzene
Match the column I with column II and mark the appropriate choice.
(A)(iii),(B)(iv),(C)(i),(D)(ii)
(A)(iv),(B)(iii),(C)(ii),(D)(i)
(A)(i),(B)(ii),(C)(iii),(D)(iv)
(A)(ii),(B)(iii),(C)(iv),(D)(i)
Methyl alcohol is industrially prepared by the action of
CO+H2
CH3COCH3
CH3COOH
C2H5OH
Which of the following statements is not correct about methanol?
it can be prepared by reduction of formaldehyde with LiAlH4
it is used for drinking purposes
it is miscible with water in all proportions.
it is highly poisonous compound
The enzyme which can catalyst the conversion of glucose to ethanol is
zymase
diastase
invertase
maltase
An organic compound A containing C,H & O has a pleasant odour with boiling point of 78℃. On is produced which decolourles bromine water and alkaline KMnO4. The organic liquid A is
C2H5Cl
C2H5OH
C2H5COOCH3
C2H6
An equimolar quantities of ethanol & propanol is heated with con.H2SO4. The product formed is/are
C3H7OC3H7
C2H5OC3H7
C2H5OC2H5
all of these
Which of the following alcohols gives the best yield of dialkyl ether on being heated with a trace of sulphuric acid?
2-methyl-2-butanol
1-pentanol
2-pentanol
2-propanol
Ether is obtained from ethyl alcohol in presence of H2SO4 at
443K
213K
113K
413K
Ethers are prepared by the reaction of sodium alkoxide and alkyl halides. Which of the following reagents should be taken to prepare methyl tert-butyl ether?
CH3Br+NaO(CH3)3
(CH3)2C-Br+NaOCH2CH3
(CH3)3C-Br+NaOCH3
CH3CH2Br+NaOC(CH3)2
Identify X,Y & Z in the following sequence of reactions
CH3CH=CH2 CH3CH2CH2Br CH3CH2OCH2CH3
CH3CH=CH2 CH3CH2CH2Br CH3CH2CH2OCH3
CH3CH=CH2 CH3CH(Br)CH2Br CH3CH(OH)CH3
CH3CH=CH2 CH3CH(Br)CH3 CH3CH2OCH2CH3
Ethers have lower boiling points than their corresponding isomeric alcohols because of
hydrogen bonding in ethers due to high polarity
hydrogen bonding in alcohols that is absent in ether due to low polarity
insolubility of ethers in water due to less polarity
inertness of ethers as compared to alcohols
Correct order of boiling points among the following is CH3(CH2)3CH3, C2H5OC2H5, CH3(CH2)3OH
Z>X>Y
Z>Y>X
Y>X>Z
X>Y>Z
Diethyl ether when refluxed with excess of HI gives two molecules of _____(i)____ . Ethers can be more commonly prepared by reaction of ____(ii)____ & ____(iii)___
The method is called _____(iv)______. (i),(ii),(iii)& (iv) respectively are
ethanol, alcohol. Alkyl halide, substitution
ethyl iodide, phenol, ethyl iodide, esterification
ethyl iodide , sodium alkoxide, alkyl halide , Williamson’s synthesis
methyl iodide, Grignard’s reagent, alkyl halide, Williamson’s synthesis
Compound C2H6O has two isomers X & Y . On the reaction with HI, X gives alkyl halide and water while Y gives alkyl iodide and alcohol. Compounds X & Y are respectively
C2H5OH & CH3OCH3
C2H5OC2H5 & CH3OC2H5
CH3OH & CH3OCH3
CH3OCH3 & C2H5OCH3
Which of the following are the product shown by the reaction of methoxyethane with HI?
CH3I+H2O
C2H5OH+H2O
C2H5I+CH3OH
C2H5OH+CH3I
Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH yields
m-cresol
o-cresol
2,4-dihydroxytoulene
benzyl alcohol
How many alcohols with molecular formula C4H10O are chiral in nature?
4
2
1
3
What is the correct order of reactivity of alcohols in the following reaction?
3°>2°>1°
1°>2°>3°
1°<2°>3°
3°>1°>2°
CH3CH2OH can be converted into CH3CHO by
treatment with LiAlH4
catalytic hydrogenation
treatment with KMnO4
treatment with pyridinium chlorochromate
The process of converting alkyl halides into alcohols involves
substitution reaction
rearrangement reaction
addition reaction
dehydrohalogenation reaction
Anisole on reaction with chloromethane in presence of anhydrous AlCl3 gives
p-methyl anisole & p-methoxy anisole
o-methoxy acetophenone & p-methoxy acetophenone
o-methyl anisole & p-methoxy anisole
o-methyl anisole & p-methyl anisole
Match the column I with column II and mark the appropriate choice.
(A)(ii),(B)(iii),(C)(iv),(D)(i)
(A)(iv),(B)(i),(C)(ii),(D)(iii)
(A)(i),(B)(iii),(C)(ii),(D)(iv)
(A)(iv),(B)(ii),(C)(iii),(D)(i)
Match the column I with column II and mark the appropriate choice.
(A)(ii),(B)(iii),(C)(iv),(D)(i)
(A)(iii),(B)(i),(C)(ii),(D)(iv)
(A)(iv),(B)(i),(C)(ii),(D)(iii)
(A)(i),(B)(iii),(C)(ii),(D)(iv)
Match the column I with column II and mark the appropriate choice.
(A)(vi),(B)(v),(C)(ii),(D)(iv),(E)→(i),(F)→(iii)
(A)(ii),(B)(iv),(C)(i),(D)(iii),(E)→(v),(F)→(vi)
(A)(v),(B)(ii),(C)(iv),(D)(vi),(E)→(iii),(F)→(i)
(A)(iv),(B)(i),(C)(vi),(D)(v),(E)→(iii),(F)→(ii)
Boiling point of ethyl alcohol is greater than ether due to
London forces
hydrogen bonding
Van der waals force
Polarity
