Question

[n the following reaction, final mixture contains: O=c1oc2ccccc2o1 $\frac{\text { (i) } \mathrm{Ph} \mathrm{MgCl}(\mathrm{excess})}{\text { (ii) } \mathrm{NH}_{4} \mathrm{Cl}}$ (A) Oc1ccccc1O (B) OC(c1ccccc1)(c1ccccc1)c1ccccc1 (C) OC1(c2ccccc2)Oc2ccccc2O1 (D) c1ccccc1

Short answer

The final mixture in the given reaction contains the compound represented by the SMILES notation \(OC1(c2ccccc2)Oc2ccccc2O1\).

Step-by-step solution

Identify the reactive sites in the starting material

We need to identify the reactive site(s) in the given starting material (SMILES: O=c1oc2ccccc2o1). The structure contains a cyclic ester (lactone) moiety. The carbonyl group in a lactone is electrophilic and can react with nucleophiles, such as a Grignard reagent.

Reaction with the Grignard reagent

The Grignard reagent used in step (i) is phenyl magnesium chloride, which can act as a nucleophile due to its negatively charged carbon atom. The nucleophilic attack of the phenyl group from the Grignard reagent will take place at the electrophilic carbonyl carbon of the lactone, causing the π bond between the carbonyl carbon and oxygen to break, resulting in the formation of an alkoxide intermediate. Since an excess of the Grignard reagent is used, this process will occur twice, opening the cyclic ester and replacing both carbonyl groups with phenyl groups.

Reaction with ammonium chloride

In step (ii), the intermediate reacts with ammonium chloride (NH4Cl). The alkoxide oxygen will act as a base, abstracting a proton from the ammonium ion (NH4+), resulting in the formation of an alcohol at each oxygen site. The final product will be a diol, with two phenyl groups attached to each of the carbons that originally formed the ester.

Identify the final product

Comparing the structure of the final product obtained in step 3 with the given options, we find that it matches option (C), with the SMILES notation: OC1(c2ccccc2)Oc2ccccc2O1. This is the correct answer to the exercise. So, the final mixture in the given reaction contains the compound represented by the SMILES notation \(OC1(c2ccccc2)Oc2ccccc2O1\).