Questions: NaCN, DMSO, O*C

Transcript text: $\xrightarrow[\substack{\text { DMSO } \\ \mathrm{O}^{*} \mathrm{C}}]{\mathrm{NaCN}}$

Solution

Solution Steps

Step 1: Identify the reaction type

The reaction is an S_N2 reaction. Sodium cyanide (NaCN) in dimethyl sulfoxide (DMSO) acts as a nucleophile, attacking the carbon atom attached to the bromine atom.

Step 2: Identify the nucleophile and leaving group

The nucleophile is the cyanide ion (CN^-) from NaCN. The leaving group is the bromine atom (Br).

Step 3: SN2 Mechanism

In an S_N2 reaction, the nucleophile attacks the carbon atom from the backside, while the leaving group departs simultaneously. This leads to an inversion of configuration at the chiral center.

Step 4: Product formation

The cyanide ion replaces the bromine atom, resulting in the formation of a nitrile group. The product will have an inverted configuration compared to the starting material.