Q19-7P - Organic Chemistry (Mcmurry)

Question

When dissolved in water, trichloroacetaldehyde exists primarily as its hydrate, called chloral hydrate. Show the structure of chloral hydrate.

Step-by-Step Solution

Answer

Step 1:Nucleophile addition Reaction

Nucleophile addition Reactions are shown by a carbonyl group, e.g., aldehyde and ketone have a carbonyl group.

Nucleophiles attack the carbonyl carbon, which is having partially positive charge due to the shift of electron density toward a more electronegative oxygen atom.

Step 2:Structure of Chloral hydrate formed

Trichloroacetaldehyde reacts with water; the neutral nucleophile $\left({\text{H}}_{\text{2}}\text{O}\right)$ adds to the carbonyl group to give an alkoxide ion intermediate, which is subsequently protonated by taking the hydrogen ion $\left({\text{H}}^{\text{+}}\right)$ from the water acting as the nucleophile to form the chloral hydrate.

 

The formation and the structure of chloral hydrate are shown as follows:

Structure of Chloral hydrate