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Published on: 04/11/2019
Hydroxy Compounds and Ethers
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1.
Write the chemical equation for Williamson synthesis of 2-ethoxy – 2- methyl pentane starting from ethanol and 2 – methyl pentan -2-ol.
2.
Write Kolbe’s reaction.
3.
How is phenol prepared from
i) chloro benzene
ii) isopropyl benzene
4.
Write the mechanism of acid catalysed dehydration of ethanol to give ethene.
5.
What happens when 1-phenyl ethanol is treated with acidified KMnO4.
6.
How are the following conversions effected
i) benzylchloride to benzylalcohol
ii) benzyalalcohol to benzoic acid
7.
What is metamerism? Give the structure and IUPAC name of metamers of 2-methoxy propane
8.
Write the structure of the aldehyde, carboxylic acid and ester that yield 4- methylpent -2-en-1-ol.
1.
2.
In this reaction, phenol is first converted into sodium phenoxide which is more reactive than phenol towards electrophilic substitution reaction with CO2, Treatment of sodium phenoxide with CO2 at 400 K, 4-7 bar pressure followed by acid hydrolysis gives salicylic acid.
3.
(i) Chloro benzene:
When Chlorobenzene is hydrolysed with 6-8% NaOH at 300 bar and 633K in a closed vessel, sodium phenoxide is formed which on treatment with dilute HCl gives phenol.
(ii) isopropyl benzene:
A mixture of benzene and propene is heated at 523K in a closed vessel in presence of H3PO4 catalyst gives cumene (isopropylbenzene). On passing air to a mixture of cumene and 5% aqueous sodium carbonate solution, cumene hydro peroxide is formed by oxidation. It is treated with dilute acid to get phenol and acetone. Acetone is also an important byproduct in this reaction.
4.
\({ CH }_{ 3 }-{ CH }_{ 2 }-OH\overset { { H }_{ 2 }{ SO }_{ 4 } }{ \underset { 443k }{ \longrightarrow } } { CH }_{ 2 }={ CH }_{ 2 }+{ H }_{ 2 }O\)
Mechanism
Primary alcohols undergo dehydration by E2 mechanism
5.
6.
(i) Benzylchloride to benzylalcohol
\(\underset { Benzyl \ chloride }{ { C }_{ 6 }{ H }_{ 5 }{ CH }_{ 2 }Cl } + NaOH { \longrightarrow } \underset { Benzyl \ alcohol }{ { C }_{ 6 }{ H }_{ 5 }{ CH }_{ 2 }OH } +NaCl\)
(ii) benzyalalcohol to benzoic acid
\(\underset { Benzyl \ alcohol }{\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH} }\stackrel{\mathrm{Na}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}^{+}}{\longrightarrow}\underset { Benzaldehyde } {\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}}\stackrel{\mathrm{Na}_{2} \mathrm{CrO}_{7} / \mathrm{H}^{+}}{\longrightarrow} \underset { Benzoic \ acid } {\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}}\)
7.
Ethers having same molecular formula, but alkyl groups attached to the oxygen atom are different. This phenomenon is known as metamerism.
Metamers of 2- methoxy propane
\(\mathrm{C}_{2} \mathrm{H}_{5}-\mathrm{O}-\mathrm{C}_{2} \mathrm{H}_{5}-\) diethyl ether
\(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\) methyl n-propyl ether
8.
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