The correct sequence of reactions for the synthesis of the following molecule is(are)
The correct sequence of reactions for the synthesis of the following molecule is(are)
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- (i) 4-Iodophenol, Mg, ether
(ii) Cyclopropane carboxaldehyde, THF
(iii) CsCO₃, MeI, THF - (i) Cyclopropyl bromide, Mg, ether
(ii) 4-Hydroxybenzaldehyde, THF
(iii) CsCO₃, MeI, THF - (i) 4-Iodophenol, CsCO₃, MeI, THF
(ii) Mg, ether
(iii) Cyclopropane carboxaldehyde, THF - (i) Cyclopropyl bromide, Mg, ether
(ii) Methyl 4-methoxybenzoate, THF
The Correct Option is C
Solution and Explanation
To synthesize the given molecule, we need to consider the steps in a strategic sequence, ensuring each chemical reaction aligns with desired transformations in the target compound.
The correct sequence of reactions is as follows:
- Step 1: Methylation of 4-Iodophenol
Starting with 4-Iodophenol, we use cesium carbonate (CsCO₃) and methyl iodide (MeI) in tetrahydrofuran (THF) to introduce a methoxy group at the para position. This produces 4-Methoxy-phenol.
\(\text{4-Iodophenol} \xrightarrow{\text{CsCO}_3/\text{MeI}} \text{4-Methoxyphenol}\) - Step 2: Formation of Grignard Reagent
Next, we convert 4-Methoxyphenol into a Grignard reagent using magnesium (Mg) in ether. This step prepares the molecule to react with an aldehyde.
\(\text{4-Methoxyphenol} \xrightarrow{\text{Mg/ether}} \text{Grignard Reagent}\) - Step 3: Addition to Cyclopropane Carboxaldehyde
The Grignard reagent then reacts with cyclopropane carboxaldehyde in THF. The addition of the Grignard reagent to the aldehyde forms a secondary alcohol, specifically attaching the cyclopropane ring to the aromatic structure.
\(\text{Grignard Reagent} + \text{Cyclopropane Carboxaldehyde} \rightarrow \text{Target Molecule}\)
The sequence in the correct option ensures all functional groups are introduced and manipulated in a logical manner that aligns with standard organic synthesis techniques.
Correct Answer: Option 3
(i) 4-Iodophenol, CsCO₃, MeI, THF
(ii) Mg, ether
(iii) Cyclopropane carboxaldehyde, THF
By following these steps, we efficiently synthesize the target molecule with the desired arrangement of functional groups.
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