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?

Question

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? (A)  (B)  (C)  (D) H2C = O

Tardigrade Admin · Accepted Answer

B is a tertiary alcohol based on given properties.
(a)

C H_{2} - C ∣∣ O H_{2} + C H_{3} C H_{2} M g I H_{3} O^{+}

1^{\circ} alcohol C H_{3} C H_{2} C H_{2} C H_{2} O H

(b)

C H_{3} C H_{2} C ∣∣ O C H_{3} + C H_{3} C H_{2} M g I H_{3} O^{+}

3^{\circ} alcohol C H_{3} C H_{2} C ∣ H_{3} C ∣ O H H C H_{2} C H_{3}

(c)

C H_{3} C H O + C H_{3} C H_{2} M g I H_{3} O^{+} 2^{\circ} alcohol C H_{3} O ∣ H C H C H_{2} C H_{3}

(d)

H C H O + C H_{3} C H_{2} M g I H_{3} O^{+} 1^{\circ} alcohol C H_{3} C H_{2} C H_{2} O H

Q. 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 $P D C$ in dichloromethane. Which of the following is a possible compound for $A$ ?

$H_{2} C = O$

Q. 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?

H2​C=O

Q. 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 $P D C$ in dichloromethane. Which of the following is a possible compound for $A$ ?

$H_{2} C = O$