What is the product of reaction of triphenylmethanol heated up with 40% HI in glacial acetic acid and then treated with sodium bisulfite?
calculate the percent yield of 4-bromoacetanilide
To determine the product of this reaction, we can break down the reaction steps and analyze each one.
Step 1: Reaction of triphenylmethanol with 40% HI in glacial acetic acid.
When triphenylmethanol (also known as triphenylcarbinol) is heated with 40% hydroiodic acid (HI) in glacial acetic acid, it undergoes an acid-catalyzed dehydration reaction known as the Appel reaction. This reaction typically involves the conversion of an alcohol into an alkyl iodide. Specifically, the hydroxyl group (-OH) in triphenylmethanol is replaced by an iodine atom (-I) from HI.
The equation for this reaction can be represented as follows:
C6H5-CH(OH)-C6H5 + HI → C6H5-CH(I)-C6H5 + H2O
Step 2: Treatment with sodium bisulfite.
After the Appel reaction, the product is treated with sodium bisulfite (NaHSO3). Sodium bisulfite is commonly used as a reducing agent and can react with various carbonyl compounds, including the alkyl iodide formed in the previous step. The reaction with sodium bisulfite leads to the formation of a sulfonic acid compound.
The equation for this reaction can be represented as follows:
C6H5-CH(I)-C6H5 + NaHSO3 → C6H5-SO3H + NaI
Therefore, the product of the given reaction sequence is a sulfonic acid compound, specifically triphenylmethanesulfonic acid (C6H5-SO3H).
In summary, the overall reaction sequence can be summarized as follows:
Triphenylmethanol + HI → Triphenylmethyliodide + H2O
Triphenylmethyliodide + NaHSO3 → Triphenylmethanesulfonic acid + NaI