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Questions
How will you bring about the following conversion in not more than two steps?
Ethanol to 3-Hydroxybutanal
How will you convert the following:
Ethanol to 3-Hydroxybutanal
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Solution 1
\[\begin{array}{cc}
\phantom{...............................................................}\ce{OH}\\
\phantom{.............................................................}|\\
\ce{\underset{Ethanal}{CH3 - CH2 - OH}->[Mild oxidation][KMnO4/dil.H2SO4]\underset{(Two molecules)}{\underset{Acetaldehyde}{CH3 - CHO}}->[dil.OH-][warm]\underset{3-Hydroxybutanal}{CHO - CH2 - CH - CH3}}\
\end{array}\]
Solution 2
\[\begin{array}{cc}
\phantom{....................................}\ce{OH}\\
\phantom{..................................}|\\
\ce{CH3CH2OH ->[PCC] CH3CHO ->[dil NaOH][Aldol condensation] \underset{3-Hydroxybutanal}{CH3 - CH - CH2 - CHO}}
\end{array}\]
PCC = Pyridinechlorochromate
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RELATED QUESTIONS
Write the products formed when CH3CHO reacts with the following reagents: CH3CHO in the presence of dilute NaOH
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(i) \[\ce{CH3 - CHO}\]
(ii) 
(iii) \[\begin{array}{cc}
\phantom{}\ce{O}\\
\phantom{}||\\
\ce{CH3 - C - CH3}
\end{array}\]
(iv) \[\begin{array}{cc}
\phantom{}\ce{CH3}\\
|\phantom{...}\\
\ce{CH3 - C - CHO}\phantom{..}\\
|\phantom{...}\\
\phantom{}\ce{CH3}\\
\end{array}\]
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When acetaldehyde is treated with dilute NaOH, the following reaction is observed.
\[\begin{array}{cc}
\ce{2CH3 - CHO ->[dil.NaOH] CH3 - CH - CH2 - CHO}\\
\phantom{...............}|\\
\phantom{.................}\ce{OH}
\end{array}\]
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