Predict the products of the following reactions. (c) benzyl bromide + sodium cyanide

Verified step by step guidance

1. Identify the reactants: benzyl bromide (C6H5CH2Br) and sodium cyanide (NaCN).
2. Recognize that this is a nucleophilic substitution reaction (SN2 mechanism) where the cyanide ion (CN-) will act as the nucleophile.
3. The cyanide ion (CN-) will attack the carbon atom bonded to the bromine atom in benzyl bromide, leading to the displacement of the bromine atom.
4. The bromine atom leaves as a bromide ion (Br-), and the cyanide ion (CN-) attaches to the carbon atom, forming a new carbon-carbon bond.
5. The product of the reaction is benzyl cyanide (C6H5CH2CN).

Key Concepts

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, replacing a leaving group. In this case, sodium cyanide (NaCN) acts as the nucleophile, attacking the carbon atom bonded to the bromine in benzyl bromide. This reaction typically follows either an SN1 or SN2 mechanism, depending on the structure of the substrate and the conditions.

Benzyl Bromide

Benzyl bromide is an organic compound with the formula C6H5CH2Br, consisting of a benzene ring attached to a bromomethyl group. It is a primary alkyl halide, making it a suitable substrate for nucleophilic substitution reactions. The presence of the benzene ring stabilizes the transition state during the reaction, influencing the reaction pathway and product formation.

Sodium Cyanide as a Nucleophile

Sodium cyanide (NaCN) is a strong nucleophile due to the presence of the cyanide ion (CN-), which has a high electron density. This allows it to effectively attack electrophilic centers, such as the carbon atom in benzyl bromide. The reaction of NaCN with benzyl bromide results in the formation of benzyl cyanide, a compound that can be further utilized in various organic synthesis applications.