Q22E - Organic Chemistry (Mcmurry)

Question

Predict the product (s) and provide the mechanism for each reaction below.

Step-by-Step Solution

Answer

The product prediction and its mechanism for each of the reaction can be explained.

Step 1: Production prediction and mechanism for (a)

The oxygen’s nucleophilic attack of acetamide on thionyl chloride with the chloride elimination leads to the intermediate formation then again proton can be eliminated for imine formation. There is an elimination of HCl for E₂ type of imine and methyl cyanide in a single step. The product is acetonitrile.

The formation mechanism can be denoted as,

Step 2: Production prediction and mechanism for (b)

The oxygen’s nucleophilic attack of cyclopentane carboxylamide on thionyl chloride with the chloride elimination leads to the intermediate formation then again proton can be eliminated for imine formation. There is an elimination of HCl for E₂ type of imine and production of cyclopentanenitrile in a single step. The product is cyclopentanenitrile.

The formation mechanism can be denoted as,

Step 3: Production prediction and mechanism for (c)

The oxygen’s nucleophilic attack of benzamide on thionyl chloride with the chloride elimination leads to the intermediate formation then again proton can be eliminated for imine formation. There is an elimination of HCl for E₂ type of imine and production of benzonitrile in a single step. The product is cyclohexanenitrile.

The formation mechanism can be denoted as,

Step 4: Production prediction and mechanism for (d)

The oxygen’s nucleophilic attack of amide on thionyl chloride with the chloride elimination leads to the intermediate formation then again proton can be eliminated for imine formation. There is an elimination of HCl for E₂ type of imine and production of 1-cyanopropene in a single step. The product is cyclopentanenitrile.

The formation mechanism can be denoted as,