Emancipate: liberate :: curdle : spoil
Emancipate means to set free from legal, social, or political restrictions.
Liberate means to set someone free from a situation, especially slavery.
The words are similar, just like curdle and spoil.
Curdle means to cause to form curdles or lumps.
Spoil (in regards to food) means it cannot be eaten.
The other anologies are not similar words.