Explain how does the – OH group attached to a carbon of benzene ring activate it towards electrophilic substitution?
Phenol may be regarded as a resonance hybrid of structures I-V, shown below.
As a result of +R effect of the -OH group, the electron density in the benzene ring increases thereby facilitating the attack of an electrophile. In other words, presence of -OH group, activates the benzene ring towards electrophilic substitution reactions. Further, since the electron density is relatively higher at the two o-and one p-position, therefore electrophilic substitution occurs mainly at o-and p-positions.
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.
Assertion (A): o-Nitrophenol is less soluble in water than the m- and p-isomers.
Reason (R): m-Nitrophenol and p-Nitrophenol exists as associated molecules.
Assertion (A): Ethanol is a weaker acid than phenol.
Reason (R): Sodium ethoxide may be prepared by the reaction of ethanol with aqueous NaOH.
Explain the following with an example
(i) Kolbe's reaction (ii) Reimer – Tiemann reaction –
(iii) Williamson ether synthesis (iv) Unsymmetrical ether
How is 1-propoxypropane synthesised from propan-l-ol? Write the mechanism of this reaction.
Explain why alcohols and ethers of comparable molecular mass have different boiling points.
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.
Name the enzymes and write the reactions involved in the preparation of ethanol from sucrose by fermentation.
Assertion (A): Bond angle in ethers is slightly less than the tetrahedral angle. Reason (R): There is a repulsion between the two bulky (-R) groups.
Predict the major product of acid catalysed dehydration of
(i) 1-nicthylcyclohcxanoland
(ii) butan-1-ol
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
Write the structures of the isomers of alcohols with molecular formula C4H10O. Which one of these isomers exhibits optical activity?
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]
Which of the following is an appropriate set of reactants for the preparation of l-methoxy-4- nitrobenzene and why?
Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method.Give reason.
Preparation of alcohols from alkenes involves the electrophilic attack on alkene carbon atom. Explain its mechanism.
Assertion (A): Boiling points of alcohols and ethers are high.
Reason (R): They can form intermolecular hydrogen bonding.
Phenol can be distinguished from ethanol by the reactions with ………….
(a) Br2/water (b) Na
(c) Neutral FeCl3 (d) All of these
Explain why is OH group in phenols more strongly held as compared to OH group in alcohols.
In Kolbe's reaction, instead of phenol, phenoxide ion is treated with carbon dioxide. Why?
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
Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol.
Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact.
While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile. Give reason.
You are given benzene, cone. H2S04and NaOH. Write the equations for the preparation of phenol using these reagents.
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 .
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
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.)
