Replace Words From One List Of Strings With Another?

The code below replaces if it finds a given string from the list of contractions with its equivelant from the list of word-contractions. E.g., if it finds 'll it will replace it with Will. The code words but whtn it comes to let's it will replace it with let is.

'remove panctuation and contractions first
Dim contractions As List(Of String) = New List(Of String)(New String() _
{"'ll", "'re", "'ve", "'m", "'d", "'s", "n't", "won't", "lets", "let's", "ikon of elkomenos", "ikon of crucifixion", "ikon of crist elkomenos", "Part A", "Part B", "renaissance style", "hagios nikolaos", "full wall fortification"})

[code]....