Searching longer keywords first then eventually the shorter once

I am attempting to find a way to search for long keyword tails first before searching for the shorter once in VB.NET. My research on Google never offered a way to search for words like that. This is for my grammar checker database that has numerous amounts of words that should do the replacements in a sequence. If you were to change the shorter once first, then one would not find a way of eliminating the errors that are left by the shorter once.... The shorter once are mainly meant for enhancing the grammar. I have just found a way of eliminating the stackoverflow on my code so that will not be an issue. I only mention this because there are those who are familiar with my code! If one were to offer a solution, would it work on a context menu? I am only mentioning this because, this is the only part that needs restructuring.

Code:

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checkWord = replacements.Keys.ElementAt(nextCheckIndex)
        foundIndex = RichTextBox1.Find(checkWord, startZ, RichTextBox1.TextLength, RichTextBoxFinds.WholeWord)

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What is replacements? Assuming it's a Dictionary of some kind:

Code:

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Dim replacements As New Dictionary(Of String, String)
replacements.Add("aaa", "")
replacements.Add("aaaaa", "")
replacements.Add("a", "")
replacements.Add("aaaa", "")
replacements.Add("aa", "")

Dim orderedList As List(Of String) = replacements.Keys.Cast(Of String).OrderByDescending(Function(s) s.Length).ToList

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Quote:

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Originally Posted by .paul.

What is replacements? Assuming it's a Dictionary of some kind:

Code:

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Dim replacements As New Dictionary(Of String, String)
replacements.Add("aaa", "")
replacements.Add("aaaaa", "")
replacements.Add("a", "")
replacements.Add("aaaa", "")
replacements.Add("aa", "")

Dim orderedList As List(Of String) = replacements.Keys.Cast(Of String).OrderByDescending(Function(s) s.Length).ToList

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Hi, thanks for your help and reply!
What if its a dictionary of:

Private replacements As New Dictionary(Of String, List(Of String)). How would I implement that to allow me to search Long strings first, then eventually the shorter ones?

Replacements is a dictionary of (Of String, List(Of String))

How would one implement it in a RichTextBox search like this one:

Code:

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checkWord = replacements.Keys.ElementAt(nextCheckIndex)
        foundIndex = RichTextBox1.Find(checkWord, startZ, RichTextBox1.TextLength, RichTextBoxFinds.WholeWord)

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I tested your code is very slow! Plus, my dictionary is sorted so there is no need to sort it again! Anyway to make it work in my scenario?