Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers.
The reaction of Williamson synthesis involves SN2 attack of an alkoxide ion on a primary alkyl halide. But if secondary or tertiary alkyl halides are taken in place of primary alkyl halides, then elimination would compete over substitution. As a result, alkenes would be produced. This is because alkoxides are nucleophiles as well as strong bases. Hence, they react with alkyl halides, which results in an elimination reaction.

Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines.
(i) (CH3 )2CHNH2 (ii) CH3 (CH2 )2NH2 (iii) CH3NHCH(CH3 )2
(iv) (CH3 )3CNH2 (v) C6H5NHCH3 (vi) (CH3CH2 )2NCH3 (vii) m–BrC6H4NH2
Give one chemical test to distinguish between the following pairs of compounds.
(i) Methylamine and dimethylamine
(ii) Secondary and tertiary amines
(iii) Ethylamine and aniline
(iv) Aniline and benzylamine
(v) Aniline and N-methylaniline
Account for the following:
(i) pKb of aniline is more than that of methylamine.
(ii) Ethylamine is soluble in water whereas aniline is not.
(iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.
(iv) Although amino group is o– and p– directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline.
(v) Aniline does not undergo Friedel-Crafts reaction.
(vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines. (vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.
Write the IUPAC names of the following compounds:
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.
Draw the structures of all isomeric alcohols of molecular formula C5H12O and give their IUPAC names. (ii)Classify the isomers of alcohols in question 11.3(i)as primary, secondary and tertiary alcohols.
Explain why propanol has a higher boiling point than that of the hydrocarbon, butane.
Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact.
Alcohols, phenols, and ethers are organic compounds that can be classified based on their molecular structure and functional groups.
Classification of Alcohols:
Classification of Phenols:
Classification of Ethers:
In summary, alcohols, phenols, and ethers can be classified based on their molecular structure and functional groups. Understanding the classification of these compounds is important for predicting their reactivity and understanding their potential applications in various fields, including chemistry, biology, and industry.