[99dmg]

Cl-CH₂-CH₂-O-CH₂-O-CH₂-CH₂-Cl

Only using ethylene and formaldehyde as a carbon source?

[Dan]

Show your attempt at the question, this is Forum policy.

Hint: acetal

[99dmg]

Okay this is what I did

1) Use Cl₂ and H₂O on ethylene to produce 2-Chloroethanol

2) Use 2-Chloroethanol with formaldehyde and a strong acid to get a hemiacetal

3) React the hemiacetal from above with ethylene and Cl₂

On a side note:

Can you produce a hemiacetal using ethanol and then deprotonating it with NaH and then reacting it with the formaldehyde?

[Dan]

2) Use 2-Chloroethanol with formaldehyde and a strong acid to get a hemiacetal

This will give the target acetal. Hemicaetals are not stabe unless they're cyclic (e.g. sugars).

2ROH + H₂CO (RO)₂CH₂ + H₂O

Can you produce a hemiacetal using ethanol and then deprotonating it with NaH and then reacting it with the formaldehyde?

This is a reversible process, the hemiacetal will readily collapse back to the starting materials.

[99dmg]

Oh, thanks I see it now.

So the reaction still works even if there is a Cl on the other carbon of the ethanol molecule? That was the part I was wondering about.

[Dan]

In the absence of strong nucleophiles or bases, I don't think the chloro substituent will cause a problem.