-
Classify the following as primary,
secondary and tertiary alcohols.
(i)
(ii)
(iii)
(iv)
(v) (vi)
If
group
is present, alcohol is
(primary),
if
group
is present is
(secondary) and if
group
is present, alcohol is
.
So classify on this basis.
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Identify allylic alcohols in the above
examples.
Following groups are included in
allylic alcohols.
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Name the following compounds according to the IUPAC system.
(i)
(ii)
(iii)
(iv)
(v)
Prefix according to the C-chain;
for alcohol add suffix ?ol; for double bond ?ene; tell the position of
substituents, double bond and functional group (s).Then, given the name in the
following manner.
Name of substituent with position (in
alphabetical order) + parent C-chain name + primary suffix (antiene etc.) +
secondary suffix with position (for main functional group).
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Show how are the following alcohols prepared by the reaction
of a suitable Grignard reagent on methanol?
(i)
(ii)
. From h
here, it is clear that HCHO gives
groups,
so R of Grignard reagent is the remaining part of given alcohols. Thus, select
the suitable Grignard reagent by substituting the value of R.
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Write structures of the products of the
following reaction.
(i)
(ii)
(iii)
(i) Acidic hydration of propene
i.e., addition of
(according
to Markownikoff?s rule) result in the formation of alcohol.
(ii) Reduction of
group (not is
ester group) into ?OH.
(iii) Reduction of ?CHO group into
.
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Give structure of the products you would expect when each
of the following alcohol reacts with
(a)
(b)
and
(c)
(i) Butan-1-ol (ii)
2-methylbutan-2-ol
Replacement of ?OH by (a)
(b) ?Br
(c)
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Predict the major product of acid catalyzed dehydration of
(i) 1-methylcyclohexanol (ii) butan-1-ol
In acid catalyzed dehydration process a molecule of water is liberatedaccording to Saytzeff'srule i.e., results in the formation of moresubstituted alkene.
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Ortho and para nitrophenols are more acidic than phenol.Draw the resonance structures of the corresponding phenoxide ions.
Acidic strength depenas on the relative stabilities of correspondingphenoxide ions based on resonance.
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Write the
equations involved in the following reactions :
(i)
Reimer-Tiemann reaction
(ii)
Kolbe's reaction
(i) It
is the reaction of phenol with chloroform in the presence of sodium hydroxide,
As a result, group is
introduced at o-position of benzene ring.
(ii) Reaction
of phenol and then
with a weak
electrolyte orthooenzoic acid is formed.
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Write the reactions of Williamson synthesis of2-ethoxy-3-methyipentane starting from ethanol and 3-methyl pentan-2-ol.
(i) Reaction of3-methylpentan-2-ol with sodium.
(ii) Reaction of ethanol with hydrogen bromide.
(iii) Reaction of product formed in (i) reaction with the product of (ii).
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Which of the following is an appropriate
set of reactants for the preparation of 1-methoxy-4-nitrobenzene and why?
(i)
(ii)
This reaction involves preparation of
ether by Williamson synthesis it takes place by
attack
of an alkoxide ion on primary alkyl halide.
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Predict the products of the following
reactions.
(i)
(ii)
(iii)
(iv)
(i) and (ii)
i.e.,
primary halide is formed.
(iii) Nitration (introduction of
group)
takes place at o- and p-positions.
(iv) Tertiary iodide and primary alcohol
are formed.
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1.
Write IUPAC names of the following compounds.
(i)
(ii)
(iii)
(iv)
(v)
(vi)
(vii)
(viii)
(ix)
(x)
(xi)
(xii)
Prefix according to the carbon
chain: for alcohol (?OH) use suffix ?ol; tell the position of substitutents and
functional group. For ether (?O?), prefix alkoxy is used. For ?OH group
attached directly to benzene ring,
suffix phenol is used.
So, give the name of alcohol as substituent
with position (In alphabetical order) + prefix of carbon chain + prefix of
carbon chain + primary suffix (ane, ene, yne) + ?ol? with position and give the
name of other as alkoxy alkane (where alkoxy smaller R group and alkane is main
chain)
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Write structures of the compounds whose IUPAC names are as follows.
(i) 2-methylbutan-2-ol (ii) 1-phenylpropan-2-ol
(iii) 3, 5-dimethylhexane-1, 3, 5-triol (iv) 2, 3-diethylphenol
(v) 1-ethoxypropane (vi) 2-ethoxy-3-methylpentane
(vii) Cyclohexylmethanol (viii) 3-cyclohexylpentan-3-ol
(ix) Cyclopent-3-en-1-ol (x) 3-chloromethylpentan-1-ol
(i) Draw the main carbon chain according to the root word of carbon chain and then attach the other groups according to the positions mentioned.
(ii) Suffix ‘al’ represents -OH group and prefix 'alkoxy' represents 'RO'croup.
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(i) Draw the structures of all isomeric
alcohols of molecular formula
and give
their IUPAC names.
(ii) Classify the isomers of
alcohols in question 3. (i) as primary, secondary arid tertiary alcohols.
(i) Make different isomers by
varying the number or C-atoms in continuous chain, the position of
and
groups.
(ii) Primary
alcohols
have
group
Secondary (2°) have group
and Tertiary (3°)
have
,
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Explain why propanol has higher boiling point than that ofthe hydrocarbon, butane?
Boiling point is directly proportional to the intermolecular forces existing in a compound.
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Alcohols are comparatively more soluble in water thanhydrocarbons of comparable molecular masses. Explain this fact.
Consider polar nature of water as well as alcohol; presence of hydrogen bonding.
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What is meant by hydroboration-oxidation reaction?Illustrate it with an example.
Addition of diborane to alkenes followed by oxidation.
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Give the structures and IUPAC names of
monohydric phenols of molecular formula,
.
Ortho (1, 2 ); para (1, 4); meta (1, 3)
Draw these isomers according to the mentioned positions of ?OH and
groups.
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While separating a mixture ofortho and para nitrophenols bysteam distillation, name the isomer which will be steam volatile. Give reason.
Isomer, which is stema volatiles less strongly bonded. The other one is strongly bonded by H-bonding.
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Give the equations of reactions for the preparation of phenol from cumence.
Oxidation of cumece into cumenehydroperoxide, then acidic hydrolysis.
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Write chemical reaction for the preparation of phenol from chlorobenzene.
Reaction of chlorobenzene with sodium hydroxide folio-wed byacidification of the product formed.
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Write the mechanism of hydration of ethane to yield ethanol.
The steps involved in this process are
(1) Protonation of alkene.
(2) Nucleophilic attack of water on carbocation.
(3) Deprotonation to form an alcohol
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You are given
benzene, cone. and . Write
theequations for the preparation of phenol using these reagents,
(i)
Sulphonation of benzene.
(ii) Reaction with and
water.
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Show how will you synthesis:
(i) 1-phenylethanol form a
suitable alkene.
(ii) Cyclohexylmethanol using an
alkyl halide by an
reactions.
(iii) pentan-1-ol using a
suitable alkyl halide?
(i) Acidic hydration of ethenyl
benzene.
(ii) Alkaline hydrolysis of
cyclohexyl methyl bromide.
(iii) Alkaline hydrolysis of
1-bromopentane.
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Give two reactions that show the acidic
nature of phenol.Compare acidity of phenol with that of ethanol.
Reaction of phenol with Na and
comparing
of acidity of phenoland ethanol,
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Explain why is ortho nitrophenol more
acidic than orthomethoxyphenol?
(i)
electron
withdrawing group,
-electron
releasing group,
(ii) Presence of electron
withdrawing group increases the stability ofphenoxide ion while presence of
electron releasing group decreasesits stability.
(iii) Higher is the stability of
phenoxide ion formed, more is the acidiccharacter.
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Explain how does the —OH group attached to a carbon of benzene ring activate if towards electrophilic substitution?
Resonance effect clue to —OH group.
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Give equation of the following
reactions.
(i) Oxidation ofpropan-1-ol with
alkaline
solution.
(ii) Bromine in
with
phenol.
(iii) Dilute
with
phenol.
(iv) Treating phenol with chloroform
in presence of aqueous
.
(i) Alcohol oxidises to carboxylic
acid.
(ii) o-and p- bromophenol are formed,
(iii) Nitration (introduction of
group)
ato-andp- positions.
(v) Reimer-Tiemann reaction involves
introduction of
group
atortho position, sailcylaldehyde is formed.
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Explain the following with an example.
(i) Kolbe's reaction.
(ii) Reimer-Tiernann reaction.
(iii) Williamson ether
synthesis.
(iv) Unsymmetrical ether.
(i) (Reaction of phenol with
and
),
Salicylic acid is formed.
(ii) Reaction of phenol with
salicylaldehyde.
(iii) AlkyI halide + sod. alkoxide
Ether +
Sod. halide.
(iv) Ethers containing two different
alkyl/aryl groups.
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Write the mechanism of acid catalysed dehydration ofethanol to yield ethene.
Step involved in acid catalysed dehydration are
(i) Protonation of alcohol,
(ii) Formation of carbocation.
(iii) Elimination of a proton.
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How are the following conversion carried
out?
(i) Propene
propan-2-ol.
(ii) Benzyl chloride
Benzyl
alcohol.
(iii) Ethyl magnesium chloride
Propan-1-ol.
(iv) Methyl magnesium bromide
2-methylpropan-2-ol.
(i) Acidic hydration of propene.
(ii) Alkaline hydrolysis of
benzyl chloride.
(iii) Reaction with methanal in
dry ether followed by acid hydrolysis.
(iv) Reaction with propanone in dry ether
followed by acid hydrolysis.
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1.
Name the reagents used in the following reactions.
(i) Oxidation of a primary
alcohol to carboxylic acid.
(ii) Oxidation of a primary
alcohol to aldehyde.
(iii) Bromination of phenol to
2,4,6- tribromophenol.
(iv) Benzyl alcohol to benzole
acid.
(v) Dehydration of propan -2-ol
to propene.
(vi) Butan-2-one to butan-2-ol.
(i) Oxidising agent (strong)
(ii) Weak oxidising agent
(iii)
(iv) Strongoxidising agent
(v) Dehydrating agent
(vi) Reducing agent.
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Give reason for the higher point of ethanol in comparison to methoxymethane.
Presence of intermolecular H-bonding in ethanol, but not in ether.
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Give IUPAC names of the following
ethers.
(i)
(ii)
(iii)
(iv)
(v)
(vi)
Recall the rules of IUPAC nomenclature
see solution 1 of exercise.
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Write the names of reagents and
equations for the preparation of the following ethers by Williamson's
synthesis.
(i) 1-propoxypropane
(ii) Ethoxybenzene
(iii) 2-methoxy-2-methylpropane
(iv) 1-methoxyethane
(i)
(ii) Alkyl halide should be primary.
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Illustrate the examples the limitations of Williamson'ssynthesis for the preparation of certain types of ethers.
Tertiary alkyl halides readily give elimination product with strong baseslike alkoxide ions. The C—X bond of alkyl halide does not possess doublebond character i.e., should not be in conjugation with multiple bond.
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How is 1-propoxypropane synthesized from propan-1-ol? Write mechanism of this reaction.
(i) Williamson’s synthesis or
(ii) Dehydration of propan-1-ol
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Preparation of
ethers by acid dehydration of secondary ortertiary alcohols is not a suitable
method. Give reason.
Due to steric
hindrance, alkenes are formed by mechanism.
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Write the equation of the reaction of hydrogen iodidewith: (i) 1-propoxypropane (ii) methoxybenzene and (iii) benzyl ethyl ether.
Alcohols and alkyl of aryl iodides are formed. Generally primary halide (or lower halide) is formed in this reaction.
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Explain the fact that in aryl alkyl ethers
(i) the alkoxy group activates the benzene ring towards electrophilic substitution.
(ii) it directs the incoming substituents to ortho and para positions in benzene ring.
Consider +R effect of the alkoxy group and more electron density at o-and p-positions.
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Write the mechanism of the reaction of HI withmethoxymethane.
Steps involved in this process are
(i) protonation
(ii) formation of methanol and iodomethane.
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Write equations of the following
reactions.
(i) Friedel Crafts
reaction-alkylation ofanisole.
(ii) Nitration of anisole.
(iii) Bromination ofanisole in
ethanoic acid medium,
(iv) Priedel Crafts acetylation
of anisole.
group is
directing.
(i) Adulation (i.e.,
introduction of R group) at- o and p-positions. (By anhyd.
),
(ii) Nitration (i.e..
introduction of
group) at
o-and p-positions (B
).
(iii) Bromination (introduction
of
group)
ato-ando-positions (By
in
).
(iv) Acetylation (introduction of
RCO-group) at o-and p-position (By
-anhydrous
).
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Show how would you synthesis the
following alcohols from appropriate alkenes?
(i) (ii)
(iii) (iv)
By hydration (addition of
)
appropriate alkenes in accordance with Markownkoff?s rule.
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When 3-methylbutane-2-ol is treated with
HBr, the following reaction takes place
Give a mechanism for this
reaction.
The secondary carbocation formed in the
process rearranges to a more stable tertiary carbocation by a hydride ion shift
from 3rd carbon atom.
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question_answer46)
Mono
chlorination of toluene in sunlight followed by hydrolysis with aq. NaOH
yields.
(a) o-Cresol (b) m-Cresol
(c) 2,4-Dihydroxytoluene
(d) Benzyl alcohol
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question_answer47)
How
many alcohols with molecular formula
are chiral in nature ?
(a) 1 (b) 2
(c) 3 (d) 4
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question_answer48)
What
is the correct order of reactivity of alcohols in the following reaction ?
(a) (b)
(c) (d)
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question_answer49)
can be
converted into
by....... .
(a) catalytic hydrogenadon
(b) treatment with
(c) treatment with pyridinium chlorochromate
(d) treatment with
View Answer play_arrow
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question_answer50)
The
process of converting alkyl halides into alcohols involves.......
(a) addition reaction
(b) substitution reaction
(c) dehydrohalogenation reaction
(d) rearrangement reaction
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question_answer51)
Which
of the following compounds is aromatic alcohol?
(a) I, II, III, IV (b) I, IV
(c) II, III (d) I
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question_answer52)
Give
IUPAC name of the compound given
below.
(a) 2-ChIoro-5-hydroxyhexane
(b) 2-Hydroxy-5-chlorohexane
(c) 5-Chlorohexan-2-ol
(d) 2-Chlorohexan-5-ol
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question_answer53)
IUPAC
name of m-cresol is .......
(a) 3-methylphenol (b) 3-chlorophenol
(c) 3-methoxyphenol (d) benzene-1, 3-diol
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question_answer54)
IUPAC
name of the compound is
..........
(a) 1-methoxy-l-methylethane
(b) 2-methoxy-2-methylethane
(c) 2-methoxypropane
(d) isopropylmethyl ether
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question_answer55)
Which
of the following species can act as the strongest base ?
(a) (b)
(c) (d)
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question_answer56)
Which
of the following compounds will react
with sodium hydroxide solution in water ?
(a) (b)
(c) (d)
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question_answer57)
Phenol
is less acidic than .......
(a) ethanol (b) o-nitrophenol
(c) o-methylphenol (d) o-methoxyphenol
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question_answer58)
Which
of the following is most acidic ?
(a) Benzyl alcohol (b) Cyclohexanol
(c) Phenol (d) w-Chlorophenol
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question_answer59)
Make
the correct order of decreasing acid strength of the following compounds.
(a) (b)
(c) (d)
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question_answer60)
Mark
the correct increasing order of reactivity of the following compounds with HBr/HCl.
(a) (b)
(c) (d)
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question_answer61)
Arrange
the following compounds in increasing order of boiling point.
Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol
(a) Propan-l-ol, butan-2-ol, butan-1-ol, pentan-1-ol
(b) Propan-l-ol, butan-1-ol, butan-2-ol, pentan-ol
(c) Pentan-l-ol, butan-2-ol, butan-1-ol, propan-l-ol
(d) Pentan-1-ol, butan-1-ol, butan-2-ol, propan-l-ol
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question_answer62)
Which
of the following are used to convert RCHO in to ?
(a) (b)
(c)
(d) Reaction with RMgX followed by hydrolysis
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question_answer63)
Which
of the following reactions will yield phenol?
(a)
(b)
(c)
(d)
View Answer play_arrow
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question_answer64)
Which
of the following reagents can be used to oxidise primary alcohols to aldehydes
?
(a) in anhydrous medium-
(b)in
acidic medium
(c) Pyridinium chlorochromate
(d) Heat in the presence of Cu at 573 K.
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question_answer65)
Phenol
can be distinguished from ethanol by the reactions with.......
(a) water (b)
Na
(c) Neutral (d)
All the above
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question_answer66)
Which
of the following are benzylic alcohols.
(a)
(b)
(c)
(d)
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question_answer67)
What
is the structure and IUPAC name of glycerol ?
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question_answer68)
Write
the lUPAC name of the following compounds.
(a)
(b)
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question_answer69)
Write
the IUPAC name of the compound given below.
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question_answer70)
Name
the factors responsible for the solubility of alcohols in water.
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question_answer71)
What
is denatured alcohol?
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question_answer72)
Suggest
a reagent for the following conversion.
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question_answer73)
Out
of 2-chloroethanol and ethanol which is more acidic and why ?
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question_answer74)
Suggest
a reagent for conversion of ethanol to ethanal.
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question_answer75)
Suggest
a reagent for conversion of ethanol to ethanoic acid.
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question_answer76)
Out
of o-nitrophenol andp-nitrophenol, which is more volatile ? Explain.
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question_answer77)
Out
of o-nitrophenol and o-cresol which is more acidic ?
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question_answer78)
When
phenol is treated with bromine water, white precipitate is obtained. Give the
structure and the name of the compound formed.
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question_answer79)
Arrange
the following compounds in increasing order of acidity and give a suitable
explanation. Phenol, o-nitrophenol, o-cresol.
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question_answer80)
Alcohols
react with active metals, e.g., Na, K, etc. to give corresponding alkoxides.
Write down the decreasing order of reactivity of sodium metal towards primary,
secondary and tertiary alcohols.
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question_answer81)
What
happens when benzenediazonium chloride is heated with water?
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question_answer82)
Arrange
the following compounds in decreasing order of
acidity.
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question_answer83)
Name
the enzymes and write the reactions involved in the preparation of ethanol from
sucrose fermentation.
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question_answer84)
How
can propan-2-one be converted into tert- butyl alcohol ?
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question_answer85)
Write
the structures of the isomers of alcohols with molecular formula Which of these exhibits
optical activity ?
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question_answer86)
Explain
why is OH group in phenols more strongly held as compared to OH group in
alcohols.
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question_answer87)
Explain
why nucleophilic substitution reactions are not very common in phenols.
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question_answer88)
Preparation
of alcohols from alkenes involves the electrophilic attack on alkene carbon
atom. Explain its mechanism.
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question_answer89)
Explain
why is O = C = O non polar while R?O?R is polar.
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question_answer90)
Why
is the reactivity of all the three classes of alcohols with cone. HCl and (Lucas reagent) different
?
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question_answer91)
Write
steps to carry out the conversion of phenol to aspirin.
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question_answer92)
Nitration
is an example of aromatic electrophilic substitution and its rate depends upon
the group already present in the benzene ring. Out of benzene and phenol, which
one is more easily nitrated and why ?
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question_answer93)
In
Kolbe's reaction, instead of phenol, phenoxide ion is treated with carbon
dioxide. Why ?
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question_answer94)
Dipole
moment of phenol is smaller than that of methanol. Why ?
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question_answer95)
Ethers
can be prepared by Williamson synthesis in which an alkyl halide is reacted
with sodium alkoxide. Di-tert-butyl ether can't be prepared by this method.
Explain.
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question_answer96)
Why
is the C?O?H bond angle in alcohols slightly less than the tetrahedral angle
where the C?O?C bond angle in ether is slightly greater ?
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question_answer97)
Explain
why low molecular mass alcohols are soluble in water.
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question_answer98)
Explain
why p-nitrophenol is more acidic than phenol.
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question_answer99)
Explain
why alcohols and ethers of comparable molecular mass have different boiling
points ?
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question_answer100)
The
carbon-oxygen bond in phenol is slightly stronger than that in methanol. Why ?
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question_answer101)
Arrange
water, ethanol and phenol in increasing order of acidity and give reason for
your answer.
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question_answer102)
Match
the structures of the compounds given in Column I with the name of the
compounds given in Column II
|
Column I
|
|
Column II
|
(a)
|
|
(i)
|
Hydroquinone
|
(b)
|
|
(ii)
|
Phenetole
|
(c)
|
|
(iii)
|
Catechol
|
(d)
|
|
(iv)
|
o-Cresol
|
(e)
|
|
(v)
|
Quinone
|
(f)
|
|
(vi)
|
Resorcinol
|
|
|
(vii)
|
Anisole
|
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question_answer103)
Match
the starting materials given in Column I with the products formed by these
(Column II) in the reaction with HI.
|
Column I
|
|
Column II
|
(a)
|
|
(i)
|
|
(b)
|
|
(ii)
|
|
(c)
|
|
(iii)
|
|
(d)
|
|
(iv)
|
|
|
(v)
|
|
(vi)
|
|
(vii)
|
|
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question_answer104)
Match
the items of column I with items of column n.
|
Column I
|
|
Column II
|
(a)
|
(a)
Antifreeze used in car engine
|
(i)
|
Neutral
ferric chloride
|
(b)
|
Solvent used in perfumes
|
(ii)
|
Glycerol
|
(c)
|
Starting material for picric acid
|
(iii)
|
Methanol
|
(d)
|
Wood spirit
|
(iv)
|
Phenol
|
(e)
|
Reagent
used for detection of phenolic group
|
(v)
|
Ethlene
glycol
|
(f)
|
By
product of soap industry used in cosmetics
|
(vi)
|
Ethanol
|
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question_answer105)
Match
the items of Column I with items of Column II.
|
Column I
|
|
Column II
|
(a)
|
Methanol
|
(i)
|
Conversion
of phenol to o-hydroxysalicylic acid
|
(b)
|
Kolbe's reaction
|
(ii)
|
Ethyl
alcohol
|
(c)
|
Williamson's synthesis
|
(iii)
|
Conversion
of phenol to salicyaldehyde
|
(d)
|
Conversion
of 2° alcohol to ketone
|
(iv)
|
Wood
spirit
|
(e)
|
Reimer-Tiemann reaction
|
(v)
|
Heated
copper at 573 K
|
(f)
|
Fermentation
|
(vi)
|
Reaction
of alkyl halide with sodium alkoxide
|
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-
question_answer106)
Assertion
: Addition reaction of water to but-1-ene in acidic medium yields butan-1-ol.
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-
question_answer107)
Assertion
: p-Nitrophenol is more acidic than phenol.
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-
question_answer108)
Assertion
: IUPAC name of the compound is Ethoxy-2-methlethane
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-
question_answer109)
Assertion
: Bond angle in ethers is slightly less than the tetrahedral angle.
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-
question_answer110)
Assertion
: Boiling points of alcohols and ethers are high.
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-
question_answer111)
Assertion:
Like bromination of benzene, bromination of phenol is also carried out in the
presence of Lewis acid.
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-
question_answer112)
Assertion
: o-Nitrophenol is less soluble in water than the m- and p-isomers.
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-
question_answer113)
Assertion
: Ethanol is a weaker acid than phenol.
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-
question_answer114)
Assertion
: Phenol forms 2, 4, 6-tribromophenol on treatment with in carbon disulphide at
273 K.
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-
question_answer115)
Assertion
: Phenols give o- and p-nitrophenol on nitration with .cone. and mixture.
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-
question_answer116)
Write
the mechanism of the reaction of HI with methoxybenzene.
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-
question_answer117)
(a)
Name the starting material used in the industrial preparation of phenol.
(b) Write complete reaction for the bromination of phenol in
aqueous and non aqueous medium.
(c) Explain why Lewis acid is not required in
bromination of phenol.
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-
question_answer118)
How
can phenol be converted to aspirin ?
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-
question_answer119)
Explain
a process in which a biocatalyst is used in industrial preparation of a
compound known to you-
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