Question

Complete the arrow pushing mechanism from benzyl chloride to benzyl alcohol by adding missing curved arrows.

Answer 1

The arrow-pushing mechanism for the conversion of benzyl chloride to benzyl alcohol involves nucleophilic substitution. The nucleophile, often represented as OH⁻, attacks the electrophile (benzyl chloride), leading to the formation of benzyl alcohol.

Step-by-step explanation:

In the first step of the reaction, the lone pair of electrons on the oxygen atom of the nucleophile (OH⁻) attacks the electrophile (benzyl chloride). This results in the formation of a new bond between the oxygen and the benzyl carbon, breaking the bond between the benzyl carbon and the chloride ion. This step is represented by a curved arrow starting from the lone pair on oxygen and pointing towards the carbon of benzyl chloride.

In the second step, the chloride ion, now detached from the benzyl carbon, takes one of the electrons from the carbon-chlorine bond, completing its octet. Simultaneously, the electrons in the carbon-carbon bond shift towards the carbon that was initially bonded to chlorine. This step is represented by a curved arrow starting from the bond between carbon and chlorine and pointing towards the carbon, indicating the movement of electrons.

The result of these steps is the formation of benzyl alcohol from benzyl chloride. The oxygen of the hydroxyl group is bonded to the benzyl carbon, and the chloride ion is expelled. This arrow-pushing mechanism helps illustrate the flow of electrons and the transformation of reactants into products during the chemical reaction.

Answer 2

The mechanism from benzyl chloride to benzyl alcohol involves a hydroxide ion attacking the carbon atom bonded to chlorine, followed by the departure of the chloride ion to form benzyl alcohol.

Step-by-step explanation:

The question is asking to complete the arrow pushing mechanism for the conversion of benzyl chloride to benzyl alcohol. In a nucleophilic substitution reaction, typically a hydroxide ion (OH⁻) is the nucleophile that attacks the electrophilic carbon atom bearing the chlorine atom in benzyl chloride. The curved arrow originates from the lone pair of electrons on the oxygen of the hydroxide ion, pointing towards the carbon atom to which the chlorine is attached, indicating the formation of a new bond. The second curved arrow originates at the carbon-chlorine bond and points towards the chlorine, indicating the departure of the chloride ion and the formation of benzyl alcohol.

The provided details about the parent name being benzaldehyde and placement of methyl and alcohol groups pertain to a different chemical context and are irrelevant to the mechanism from benzyl chloride to benzyl alcohol. Similarly, various other reactions mentioned such as with alkyl groups and benzene rings using aluminum chloride, as well as the transfer of electrons to form calcium chloride from Ca and Cl atoms, do not directly relate to the specific mechanism of benzyl chloride conversion.