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I like the way contractions operate and I know the difference between "it's" and "its" based on contraction and possession. That is, "it's = it is" and "its" is possessive.

However, there are some sentences when I feel justified in replacing "it is" with its contraction, but for some reason it doesn't sound right nor does it read correctly to me:

The method won't be approved because of how difficult it is to implement.

compared to

The method won't be approved because of how difficult it's to implement.

Is this a correct (or uncommon) usage of the contraction "it's"? Why does it sound awkward when spoken?

Xoque55
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    Take a look how Google's book scans How difficult it's or How difficult it's to. It's not necessarily common, but it's in use and not necessarily incorrect. (Comment is not an answer, but a hint to help provide research for (a better?) question) – SrJoven Jan 26 '15 at 20:23
  • Contractions are best left for informal and vernacular speech. Your example sounds rather officious. Words like "approved" and "implement" don't fit well with contractions and perhaps this is why it's sounding a bit off. See what I did there? – Martin Krzywinski Jan 26 '15 at 20:36
  • @Martin Krzywinski Yes. You gave a different example. OP's doesn't sound wonderful in any register. – Edwin Ashworth Jan 26 '15 at 20:46
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    Addressed (by CGEL via nohat) at Is there some rule against ending a sentence with the contraction "it's"?. – Edwin Ashworth Jan 26 '15 at 20:48
  • @SrJoven: There are over 5000 Google results for "how difficult it's" but only 15 results for "how difficult it's to". You can get 15 Google books hits for lots of completely ungrammatical sentences. – Peter Shor Jan 26 '15 at 20:52
  • @PeterShor in which way would it be ungrammatical versus simply off to the ear? There's no particular rule that it violates. – SrJoven Jan 26 '15 at 20:55
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    @SrJoven: It violates the same grammatical rule as contracting "That's what it is." to "That's what it's." See here for more details. – Peter Shor Jan 26 '15 at 21:38
  • I think you generally can't contract is or are before an infinitive, only before a noun, gerund, or adjective. – Barmar Jan 26 '15 at 22:41
  • @PeterShor Ending in contraction violates a specific part that is addressed. It's not enough to say look at the no-scaffolding rule and apply it to this. – SrJoven Jan 26 '15 at 23:21
  • @SrJoven: Did you read the accepted answer to the question I linked to? It doesn't mention a "no-scaffolding" rule. It says (quoting the Cambridge Grammar of the English Language) that you can't contract a verb if the object is preposed, that is, it comes before the verb. Here, the object is difficult and it comes before the verb. – Peter Shor Jan 26 '15 at 23:48
  • @PeterShor I saw stranded/stranding earlier in the day, forgot what word I saw, and added no-scaffolding to compensate for the mental block on that word. I want to make sure I understand your statement about "the object is difficult." Are you using is as a condition of being or a state of equality? Wouldn't difficult be an object complement? – SrJoven Jan 27 '15 at 14:56
  • @SrJoven: You're right; "difficult" is not an object but a subject complement. But the rule that you can't contract it because the complement is preposed still holds. You can't say "see how difficult it's", "See how difficult to implement it's", or "See how difficult it's to implement". You have to use "it is" in all three cases. – Peter Shor Jan 28 '15 at 00:39

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