how to convert ethene + butene to make 3-hydroxypentanal

Question

 Multistep synthesis question 

 

 

Answer 1

Assuming standard workup procedures and conditions:

1. Convert ethene to acetylenide anion by brominating it and then doing elimination with excess of sodamide;

2. Use mCPBA to turn 1-butene into an epoxide, and then react it with acetelenide from the previous sequence;

3. Use Lindlar's to partially reduce the product and follow up with a reductive ozonolysis to get the product.