Carry out the following transformations: ethane → bromoethane → butane → acetic acid → chloroacetic acid?

1) When ethane interacts with bromine, bromoethane and hydrogen bromide are formed:

C2H6 + Br2 → C2H5Br + HBr;

2) Bromoethane reacts with metallic sodium, it turns out – butane and sodium bromide:

2C2H5Br + 2Na → C4H10 + 2NaBr;

3) Butane reacts with oxygen to form acetic acid and water:

2C4H10 + 5O2 → 4CH3COOH + 2H2O;

4) In the process of interaction of acetic acid and chlorine, it turns out – chloroacetic and hydrochloric acid:

CH3COOH + Cl2 → CH2ClCOOH + HCl.