Methods of Preparation of Alcohols
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CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322923 Monochlorination of toluene in sunlight followed by hydrolysis with \(aq.\,\,{\text{NaOH}}\) yields.

1 o-Cresol
2 m-Cresol
3 2, 4-Dihydroxytoluene
4 Benzyl alcohol
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322924 Identify compound ' \({\text{B}}\) ' in following series of reactions?
Acetonitrile \(\xrightarrow{{{\text{Na/ alcohol }}}}{\text{A}}\,\,\,\xrightarrow{{{\text{NaN}}{{\text{O}}_{\text{2}}}{\text{/dil}}{\text{.HCl }}}}\,\,{\text{B}}\)

1 Ethyl amine
2 Nitroethane
3 Ethyl alcohol
4 Ethyl chloride
MHTCET
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322925 Benzylamine reacts with nitrous acid to form

1 Azobenzene
2 Benzene
3 Benzyl alcohol
4 Phenol
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322926 \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}=\mathrm{CHCHO} \stackrel{x}{\longrightarrow} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{OH}\).
In the above sequence \(\mathrm{X}\) can be

1 \(\mathrm{H}_{2} / \mathrm{Ni}\)
2 \(\mathrm{NaBH}_{4}\)
3 \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}^{+}\)
4 Both (1) and (2)
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322927 Primary alcohol can easily be prepared from primary alkyl halide via \({{\text{S}}_{\text{N}}}^{\text{2}}\) reaction with aqueous \(\mathrm{NaOH}\). However, similar method does not work for the preparation of tertiary alcohol (tertiary butanol) from tertiary butyl bromide except

1 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr}}\xrightarrow{{{\text{KOH/Ethanol}}}}\,\,\,\,\,\,\,\xrightarrow[{{\text{(ii)}}{\mkern 1mu} {{\text{H}}_{\text{2}}}{{\text{O}}_{\text{2}}}{\text{/NaOH}}}]{{{\text{(i)}}{{\text{B}}_{\text{2}}}{{\text{H}}_{\text{6}}}}}\)
2 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr}}\,\,\,\,\,\xrightarrow[{{{{\text{(}}{{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{)}}}_{\text{2}}}{\text{O}}}]{{{\text{Mg}}}}\,\,\,\,\,\,\xrightarrow[{{\text{(ii)}}{{\text{H}}_{\text{3}}}{{\text{O}}^{{\text{ + }}}}}]{{{\text{(i)}}{\mkern 1mu} {{\text{O}}_{\text{2}}}}}\)
3 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr + KOH}}\,\,\,\,\xrightarrow{{{{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{OH}}}}\,\,\,\,\,\xrightarrow[{{\text{Heat}}}]{{{{\text{H}}_{\text{2}}}{\text{S}}{{\text{O}}_{\text{4}}}}}\)
4 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr + C}}{{\text{H}}_{\text{3}}}{\text{COOAg(aq)}}\,\,\,\, \to \,\,\,\,\,\xrightarrow{{{{\text{H}}_{\text{3}}}{{\text{O}}^{{\text{ + }}}}}}\)
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CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322923 Monochlorination of toluene in sunlight followed by hydrolysis with \(aq.\,\,{\text{NaOH}}\) yields.

1 o-Cresol
2 m-Cresol
3 2, 4-Dihydroxytoluene
4 Benzyl alcohol
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322924 Identify compound ' \({\text{B}}\) ' in following series of reactions?
Acetonitrile \(\xrightarrow{{{\text{Na/ alcohol }}}}{\text{A}}\,\,\,\xrightarrow{{{\text{NaN}}{{\text{O}}_{\text{2}}}{\text{/dil}}{\text{.HCl }}}}\,\,{\text{B}}\)

1 Ethyl amine
2 Nitroethane
3 Ethyl alcohol
4 Ethyl chloride
MHTCET
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322925 Benzylamine reacts with nitrous acid to form

1 Azobenzene
2 Benzene
3 Benzyl alcohol
4 Phenol
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322926 \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}=\mathrm{CHCHO} \stackrel{x}{\longrightarrow} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{OH}\).
In the above sequence \(\mathrm{X}\) can be

1 \(\mathrm{H}_{2} / \mathrm{Ni}\)
2 \(\mathrm{NaBH}_{4}\)
3 \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}^{+}\)
4 Both (1) and (2)
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322927 Primary alcohol can easily be prepared from primary alkyl halide via \({{\text{S}}_{\text{N}}}^{\text{2}}\) reaction with aqueous \(\mathrm{NaOH}\). However, similar method does not work for the preparation of tertiary alcohol (tertiary butanol) from tertiary butyl bromide except

1 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr}}\xrightarrow{{{\text{KOH/Ethanol}}}}\,\,\,\,\,\,\,\xrightarrow[{{\text{(ii)}}{\mkern 1mu} {{\text{H}}_{\text{2}}}{{\text{O}}_{\text{2}}}{\text{/NaOH}}}]{{{\text{(i)}}{{\text{B}}_{\text{2}}}{{\text{H}}_{\text{6}}}}}\)
2 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr}}\,\,\,\,\,\xrightarrow[{{{{\text{(}}{{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{)}}}_{\text{2}}}{\text{O}}}]{{{\text{Mg}}}}\,\,\,\,\,\,\xrightarrow[{{\text{(ii)}}{{\text{H}}_{\text{3}}}{{\text{O}}^{{\text{ + }}}}}]{{{\text{(i)}}{\mkern 1mu} {{\text{O}}_{\text{2}}}}}\)
3 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr + KOH}}\,\,\,\,\xrightarrow{{{{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{OH}}}}\,\,\,\,\,\xrightarrow[{{\text{Heat}}}]{{{{\text{H}}_{\text{2}}}{\text{S}}{{\text{O}}_{\text{4}}}}}\)
4 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr + C}}{{\text{H}}_{\text{3}}}{\text{COOAg(aq)}}\,\,\,\, \to \,\,\,\,\,\xrightarrow{{{{\text{H}}_{\text{3}}}{{\text{O}}^{{\text{ + }}}}}}\)
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CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322923 Monochlorination of toluene in sunlight followed by hydrolysis with \(aq.\,\,{\text{NaOH}}\) yields.

1 o-Cresol
2 m-Cresol
3 2, 4-Dihydroxytoluene
4 Benzyl alcohol
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322924 Identify compound ' \({\text{B}}\) ' in following series of reactions?
Acetonitrile \(\xrightarrow{{{\text{Na/ alcohol }}}}{\text{A}}\,\,\,\xrightarrow{{{\text{NaN}}{{\text{O}}_{\text{2}}}{\text{/dil}}{\text{.HCl }}}}\,\,{\text{B}}\)

1 Ethyl amine
2 Nitroethane
3 Ethyl alcohol
4 Ethyl chloride
MHTCET
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322925 Benzylamine reacts with nitrous acid to form

1 Azobenzene
2 Benzene
3 Benzyl alcohol
4 Phenol
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322926 \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}=\mathrm{CHCHO} \stackrel{x}{\longrightarrow} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{OH}\).
In the above sequence \(\mathrm{X}\) can be

1 \(\mathrm{H}_{2} / \mathrm{Ni}\)
2 \(\mathrm{NaBH}_{4}\)
3 \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}^{+}\)
4 Both (1) and (2)
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322927 Primary alcohol can easily be prepared from primary alkyl halide via \({{\text{S}}_{\text{N}}}^{\text{2}}\) reaction with aqueous \(\mathrm{NaOH}\). However, similar method does not work for the preparation of tertiary alcohol (tertiary butanol) from tertiary butyl bromide except

1 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr}}\xrightarrow{{{\text{KOH/Ethanol}}}}\,\,\,\,\,\,\,\xrightarrow[{{\text{(ii)}}{\mkern 1mu} {{\text{H}}_{\text{2}}}{{\text{O}}_{\text{2}}}{\text{/NaOH}}}]{{{\text{(i)}}{{\text{B}}_{\text{2}}}{{\text{H}}_{\text{6}}}}}\)
2 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr}}\,\,\,\,\,\xrightarrow[{{{{\text{(}}{{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{)}}}_{\text{2}}}{\text{O}}}]{{{\text{Mg}}}}\,\,\,\,\,\,\xrightarrow[{{\text{(ii)}}{{\text{H}}_{\text{3}}}{{\text{O}}^{{\text{ + }}}}}]{{{\text{(i)}}{\mkern 1mu} {{\text{O}}_{\text{2}}}}}\)
3 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr + KOH}}\,\,\,\,\xrightarrow{{{{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{OH}}}}\,\,\,\,\,\xrightarrow[{{\text{Heat}}}]{{{{\text{H}}_{\text{2}}}{\text{S}}{{\text{O}}_{\text{4}}}}}\)
4 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr + C}}{{\text{H}}_{\text{3}}}{\text{COOAg(aq)}}\,\,\,\, \to \,\,\,\,\,\xrightarrow{{{{\text{H}}_{\text{3}}}{{\text{O}}^{{\text{ + }}}}}}\)
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CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322923 Monochlorination of toluene in sunlight followed by hydrolysis with \(aq.\,\,{\text{NaOH}}\) yields.

1 o-Cresol
2 m-Cresol
3 2, 4-Dihydroxytoluene
4 Benzyl alcohol
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322924 Identify compound ' \({\text{B}}\) ' in following series of reactions?
Acetonitrile \(\xrightarrow{{{\text{Na/ alcohol }}}}{\text{A}}\,\,\,\xrightarrow{{{\text{NaN}}{{\text{O}}_{\text{2}}}{\text{/dil}}{\text{.HCl }}}}\,\,{\text{B}}\)

1 Ethyl amine
2 Nitroethane
3 Ethyl alcohol
4 Ethyl chloride
MHTCET
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322925 Benzylamine reacts with nitrous acid to form

1 Azobenzene
2 Benzene
3 Benzyl alcohol
4 Phenol
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322926 \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}=\mathrm{CHCHO} \stackrel{x}{\longrightarrow} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{OH}\).
In the above sequence \(\mathrm{X}\) can be

1 \(\mathrm{H}_{2} / \mathrm{Ni}\)
2 \(\mathrm{NaBH}_{4}\)
3 \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}^{+}\)
4 Both (1) and (2)
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322927 Primary alcohol can easily be prepared from primary alkyl halide via \({{\text{S}}_{\text{N}}}^{\text{2}}\) reaction with aqueous \(\mathrm{NaOH}\). However, similar method does not work for the preparation of tertiary alcohol (tertiary butanol) from tertiary butyl bromide except

1 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr}}\xrightarrow{{{\text{KOH/Ethanol}}}}\,\,\,\,\,\,\,\xrightarrow[{{\text{(ii)}}{\mkern 1mu} {{\text{H}}_{\text{2}}}{{\text{O}}_{\text{2}}}{\text{/NaOH}}}]{{{\text{(i)}}{{\text{B}}_{\text{2}}}{{\text{H}}_{\text{6}}}}}\)
2 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr}}\,\,\,\,\,\xrightarrow[{{{{\text{(}}{{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{)}}}_{\text{2}}}{\text{O}}}]{{{\text{Mg}}}}\,\,\,\,\,\,\xrightarrow[{{\text{(ii)}}{{\text{H}}_{\text{3}}}{{\text{O}}^{{\text{ + }}}}}]{{{\text{(i)}}{\mkern 1mu} {{\text{O}}_{\text{2}}}}}\)
3 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr + KOH}}\,\,\,\,\xrightarrow{{{{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{OH}}}}\,\,\,\,\,\xrightarrow[{{\text{Heat}}}]{{{{\text{H}}_{\text{2}}}{\text{S}}{{\text{O}}_{\text{4}}}}}\)
4 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr + C}}{{\text{H}}_{\text{3}}}{\text{COOAg(aq)}}\,\,\,\, \to \,\,\,\,\,\xrightarrow{{{{\text{H}}_{\text{3}}}{{\text{O}}^{{\text{ + }}}}}}\)
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CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322923 Monochlorination of toluene in sunlight followed by hydrolysis with \(aq.\,\,{\text{NaOH}}\) yields.

1 o-Cresol
2 m-Cresol
3 2, 4-Dihydroxytoluene
4 Benzyl alcohol
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322924 Identify compound ' \({\text{B}}\) ' in following series of reactions?
Acetonitrile \(\xrightarrow{{{\text{Na/ alcohol }}}}{\text{A}}\,\,\,\xrightarrow{{{\text{NaN}}{{\text{O}}_{\text{2}}}{\text{/dil}}{\text{.HCl }}}}\,\,{\text{B}}\)

1 Ethyl amine
2 Nitroethane
3 Ethyl alcohol
4 Ethyl chloride
MHTCET
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322925 Benzylamine reacts with nitrous acid to form

1 Azobenzene
2 Benzene
3 Benzyl alcohol
4 Phenol
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322926 \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}=\mathrm{CHCHO} \stackrel{x}{\longrightarrow} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{OH}\).
In the above sequence \(\mathrm{X}\) can be

1 \(\mathrm{H}_{2} / \mathrm{Ni}\)
2 \(\mathrm{NaBH}_{4}\)
3 \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}^{+}\)
4 Both (1) and (2)
CHXII11:ALCOHOLS, PHENOLS AND ETHERS

322927 Primary alcohol can easily be prepared from primary alkyl halide via \({{\text{S}}_{\text{N}}}^{\text{2}}\) reaction with aqueous \(\mathrm{NaOH}\). However, similar method does not work for the preparation of tertiary alcohol (tertiary butanol) from tertiary butyl bromide except

1 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr}}\xrightarrow{{{\text{KOH/Ethanol}}}}\,\,\,\,\,\,\,\xrightarrow[{{\text{(ii)}}{\mkern 1mu} {{\text{H}}_{\text{2}}}{{\text{O}}_{\text{2}}}{\text{/NaOH}}}]{{{\text{(i)}}{{\text{B}}_{\text{2}}}{{\text{H}}_{\text{6}}}}}\)
2 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr}}\,\,\,\,\,\xrightarrow[{{{{\text{(}}{{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{)}}}_{\text{2}}}{\text{O}}}]{{{\text{Mg}}}}\,\,\,\,\,\,\xrightarrow[{{\text{(ii)}}{{\text{H}}_{\text{3}}}{{\text{O}}^{{\text{ + }}}}}]{{{\text{(i)}}{\mkern 1mu} {{\text{O}}_{\text{2}}}}}\)
3 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr + KOH}}\,\,\,\,\xrightarrow{{{{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{OH}}}}\,\,\,\,\,\xrightarrow[{{\text{Heat}}}]{{{{\text{H}}_{\text{2}}}{\text{S}}{{\text{O}}_{\text{4}}}}}\)
4 \({\left( {{\text{C}}{{\text{H}}_{\text{3}}}} \right)_{\text{3}}}{\text{CBr + C}}{{\text{H}}_{\text{3}}}{\text{COOAg(aq)}}\,\,\,\, \to \,\,\,\,\,\xrightarrow{{{{\text{H}}_{\text{3}}}{{\text{O}}^{{\text{ + }}}}}}\)