Arrange water, ethanol and, phenol in increasing order of acidity and give reason for your answer.
Increasing order of acidity is: ethanol < water < phenol.
This is because the phenoxide ion obtained after the removal of H+ is resonance stabilised, while the ethoxide ion obtained after the removal of H+ is destabilised by +1 effect of ethyl group. Thus phenol is a stronger acid than ethanol.
Now, ethanol is a weaker acid than water because the electron releasing ethyl group increases the ethanol density on oxygen and consequently the proton will not be released easily. There is no such effect is water.
Assertion (A): Phenols give o-nitrophenol and p-nitrophenol on nitration with cone. HNO3 and H2SO4 mixture.
Reason (R): -OH group in phenol is o-,p-directing.
Write structures of the compounds whose IUPAC names are as follows:
(i)2-Methylbutan-2-ol
(ii)l-Phcnylpropan-2-ol
(iii)3,5-DimethyIhexane-l,3,5-triol
(iv)2,3-Dicthylphenol
(v)1-Ethoxypropane
(vi)2-Ethoxy-3-methylpentane
(vii) Cyclohexylmethanol
(viii) 3-Cyclohexylpcntan-3-ol
(ix)Cyclopcnt-3-en-l-ol
(x)4-ChIoro-3-ethylbutan-l-ol
Why is the C – O – H bond angle‘in alcohols slightly less than the tetrahedral angle whereas the C – O – C bond angle in ether is slightly greater?
Assertion (A): Boiling points of alcohols and ethers are high.
Reason (R): They can form intermolecular hydrogen bonding.
Assertion (A): Phenol forms 2,4, 6-tribromophenol on treatment with Br2 in carbon disulphide at 273 K.
Reason (R): Bromine polarizes in carbon disulphide.
Give equations of the following reactions:
(i)Oxidation of propan-l-ol with alkaline KMnO4 solution.
(ii)Bromine in CS2 with phenol.
(iii)Dilute HNO3 acid with phehoL
(iv)Treating phenol with chloroform in presence of aqueous NaOH.
Explain why alcohols and ethers of comparable molecular mass have different boiling points.
Assertion (A): IUPAC name of the compound
Reason (R): In IUPAC nomenclature, ether is regarded as hydrocarbon derivative in which a hydrogen atom is replaced by -OR or -OAr group [where R = alkyl group and Ar = aryl group]
Show how are the following alcohols prepared by the reaction of a suitable Grignard reagent on methanal ?
You are given benzene, cone. H2S04and NaOH. Write the equations for the preparation of phenol using these reagents.
Mark the correct increasing order of reactivity of the following compounds with HBr/HCl.
Which of the following are used to convert RCHO into RCH2OH?
(a) H2/Pd
(b) LiAlH4
(c) NaBH4
(d) Reaction with RMgX followed by hydrolysis
Arrange the following compounds in increasing order of acidity and give a suitable explanation:
Phenol, o-Nitrophenol, o-Cresol
Explain why is OH group in phenols more strongly held as compared to OH group in alcohols.
Ethers can be prepared by Williamson's synthesis in which an alkyl halide is reacted with sodium alkoxide. Di-tert-butyl ether cannot be prepared by this method. Explain.
Give structures of the products you would expect when each of the following alcohol reacts with (a)HCl-ZnCl2 (b)HBrand (c) SOCl2
(i)Butan-1-ol
(ii)2-Methylbutan-2-ol
Predict the major product of acid catalysed dehydration of
(i) 1-nicthylcyclohcxanoland
(ii) butan-1-ol
(i) Draw the structures of all isomeric alcohols of molecular formula C5HI20 and give their IUPAC names.
(ii) Classify the isomers of alcohols in question (i)as primary, secondary and tertiary alcohols.
How is 1-propoxypropane synthesised from propan-l-ol? Write the mechanism of this reaction.
Write the equation of the reaction of hydrogen iodide with (i)1-propoxypropane (ii)methoxybenzene, and (iii)benzyl ethyl ether
Explain the fact that in aryl alkyl ethers (i) the alkoxy group activates the benzene ring towards electrophilic substitution and (ii) it directs the incoming substituents to ortho and para positions in benzene ring.
When 3-methylbutant 2-ol is treated with HBr, the following reaction takes place:
Give a mechanism for this reaction.
(Hint: The secondary carbocation formed in step II rearranges to a more stable tertiary carbocation by a hydride ion shift from 3rd carbon atom.)
When phenol is treated with bromine water, white precipitate is obtained. Give the structure and the name of the compound formed.
Explain a process in which a biocatalyst is used in industrial preparation of a compound known to you.
Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact.
Show how will you synthesise
(i)1 -phenylethanol from a suitable alkene.
(ii)cyclohexylmethanol using an alkyl halide by an SN2 reaction.
(iii) Pentan-l-ol using a suitable alkyl halide?
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)Brominationofphenolto2,4,6-tribromophenol
(iv)Benzyl alcohol to benzoic acid.
(v)Dehydration of propan-2-oI to propene.
(vi)Butan-2-one to butan-2-oL .
