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An organic compound $B$ is formed by the reaction of ethyl magnesium iodide with a substance $A$, followed by treatment with dilute aqueous acid, Compound B does not react with PCC or PDC in dichloromethane. Which of the following is a possible compound for $A$ ?
Options:
- A
- B
- C
- D $\mathrm{H}_{2} \mathrm{C}=\mathrm{O}$
Solution:
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Verified Answer
The correct answer is:
$\mathrm{B}$ is a tertiary alcohol based on given properties.
(a) $\mathrm{CH}_{2}-\mathrm{CH}_{2}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgI} \stackrel{\mathrm{H}_{3} \mathrm{O}^{+}}{\longrightarrow}$ $\underset{1^{\circ} \text { alocohol }}{\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}}$
(b)
(c)
(d)
(a) $\mathrm{CH}_{2}-\mathrm{CH}_{2}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgI} \stackrel{\mathrm{H}_{3} \mathrm{O}^{+}}{\longrightarrow}$ $\underset{1^{\circ} \text { alocohol }}{\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}}$
(b)
(c)
(d)
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