One of the most efficient syntheses of (Z)-3-hexene is through a Wittig reaction. Here's a step-by-step synthesis:
1. Start with 1-bromohexane as the starting material.
2. Convert 1-bromohexane to 1-hexene by using a strong base such as sodium ethoxide or potassium tert-butoxide in an elimination reaction.
3. Take 1-hexene and make it into the desired (Z)-3-hexene through a Wittig reaction. To do this, react 1-hexene with triphenylphosphonium bromide in the presence of a strong base like potassium tert-butoxide. This will give you (Z)-3-hexene.
The reaction mechanism involves the formation of a carbanion from triphenylphosphonium bromide by deprotonation with the strong base. The carbanion then reacts with 1-hexene to form the (Z)-3-hexene product.
The (Z)-configuration is achieved when the R group of the carbanion attacks the less hindered face of the double bond, resulting in the Z-stereoisomer.
Overall, this synthesis provides a direct and efficient route to obtain (Z)-3-hexene from readily available starting materials.
Which is the most efficient synthesis of (Z)-3-hexene?
1 answer
1 answer