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$\mathrm{CH}_3 \mathrm{CHO}+\mathrm{HCHO} \xrightarrow[\text { Heat }]{\text { Dil. } \mathrm{NaOH}} A \xrightarrow[\mathrm{H}_3 \mathrm{O}^{+}]{\mathrm{HCN}} B$
The structure of compound $B$ is
Options:
The structure of compound $B$ is
- A
- B
- C
- D
Solution:
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Verified Answer
The correct answer is:
It undergoes aldol condensation to give \(\mathrm{CH}_2(\mathrm{OH}) \mathrm{CH}_2(\mathrm{CHO})\) which dehydrates to give \(\mathrm{CH}_2 \mathrm{CHCHO}\)
When this is treated with \(\mathrm{HCN} / \mathrm{H}_3 \mathrm{O}^{+}\), it gives the carboxylic acid.
\(\begin{aligned}
& \mathrm{CH}_3 \mathrm{CHO}+\mathrm{HCHO} \xrightarrow{\text { Dil. } \mathrm{NaOH}} \mathrm{CH}_2(\mathrm{OH}) \mathrm{CH}_2 \mathrm{CHO} \\
& \mathrm{CH}_2(\mathrm{OH}) \mathrm{CH}_2 \mathrm{CHO} \xrightarrow{\Delta} \mathrm{CH}_2=\mathrm{CHCHO} \\
& \mathrm{CH}_2=\mathrm{CHCHO} \xrightarrow{\mathrm{HCN}} \mathrm{CH}_2=\mathrm{CHCH}(\mathrm{OH})(\mathrm{CN}) \\
& \mathrm{CH}_2=\mathrm{CHCH}(\mathrm{OH})(\mathrm{CN}) \xrightarrow{\mathrm{H}_3 \mathrm{O}^{+}} \mathrm{CH}_2=\mathrm{CH}-\mathrm{CH}(\mathrm{COOH})(\mathrm{OH})
\end{aligned}\)
When this is treated with \(\mathrm{HCN} / \mathrm{H}_3 \mathrm{O}^{+}\), it gives the carboxylic acid.
\(\begin{aligned}
& \mathrm{CH}_3 \mathrm{CHO}+\mathrm{HCHO} \xrightarrow{\text { Dil. } \mathrm{NaOH}} \mathrm{CH}_2(\mathrm{OH}) \mathrm{CH}_2 \mathrm{CHO} \\
& \mathrm{CH}_2(\mathrm{OH}) \mathrm{CH}_2 \mathrm{CHO} \xrightarrow{\Delta} \mathrm{CH}_2=\mathrm{CHCHO} \\
& \mathrm{CH}_2=\mathrm{CHCHO} \xrightarrow{\mathrm{HCN}} \mathrm{CH}_2=\mathrm{CHCH}(\mathrm{OH})(\mathrm{CN}) \\
& \mathrm{CH}_2=\mathrm{CHCH}(\mathrm{OH})(\mathrm{CN}) \xrightarrow{\mathrm{H}_3 \mathrm{O}^{+}} \mathrm{CH}_2=\mathrm{CH}-\mathrm{CH}(\mathrm{COOH})(\mathrm{OH})
\end{aligned}\)
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