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In my Rosetta Stone program, I have found the following two sentences:

Non ha comprato nessun vestito nuovo quest'anno.

Non abbiamo vinto nessuna partita questo autunno.

Why does the former sentence use quest' while the latter uses questo to express this ~?

This page says that you use quest' when used to modify a noun starting with a vowel.

Quest’: Used with all singular nouns starting with a vowel

Questo: Used with all other masculine singular nouns

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In fact "quest'" and "questo" / "questa" are totally interchangable in case of the following word starting with a vowel, however the "quest'" form happens to be spellable with more ease due to its missing trailing vowel, which if present as in the "questo" / "questa" form would result in the speaker having to pronounce two consecutive vowels.

So the two sentences above may well be written in all these forms:

Non ha comprato nessun vestito nuovo quest'anno.
Non ha comprato nessun vestito nuovo questo anno.
Non abbiamo vinto nessuna partita quest'autunno.
Non abbiamo vinto nessuna partita questo autunno.

However, as egreg pointed out in his answer and as nico pointed out in the comments to this answer, "Non ha comprato nessun vestito nuovo questo anno." and "Non abbiamo vinto nessuna partita questo autunno." (the former in particular) both sound pretty weird to hear, and you'd better drop the "quest'" form in favor of the "questo" / "questa" form in both of these cases.

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    Technically true, in practice "questo anno" sounds very bizarre in that sentence (as @egreg explains very well in his answer). – nico Jun 30 '15 at 14:22
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    @nico I agree, that's (I think) because of the fact that no one actually says it due to the difficulty of pronouncing the two consecutive vowels, indeed I should have pointed this out in my answer. – kos Jun 30 '15 at 15:35
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The main difference between the elided form and the full one is that the former doesn't carry a tonic accent and the whole group is pronounced as if it were a single word; this applies also to truncation.

The hypothetical sentence

Non ha comprato nessun vestito nuovo questo anno.

would sound quite strange; a case where questo anno could be used is

In questo anno ho avuto difficoltà, ma penso di poterle superare

where emphasis is on questo, because the missing elision forces to place a tonic accent on the word. On the other hand, a better form for the sentence would be

Quest’anno ho avuto difficoltà, ma penso di poterle superare

and here questo anno would certainly cause eyebrow raising. The meaning of the two sentences is not exactly the same, but just by a nuance.

I'd not use questo autunno in the sentence you report, but context would help: if the sentence is followed by something in opposition, then emphasis might very well go on questo.

Note that in several cases the elision is not optional. For instance, “lo amico” is never used in current Italian (it used to be in ancient times) and it would seem talking like Vittorio Gassmann in L'armata Brancaleone, where a mock medieval language was spoken.

Elisions that were taught until rather recent times were gl’inglesi or l’estati, but they have been unused for several decades in spoken Italian.

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Ngram, questo autunno vs quest'autunno, both are correct and commonly used.

Ad explained below, questo/a may be written and pronounced as quest' if the following word start with a vowel.

"Quest'ultimo" si scrive con l'apostrofo o no? (Treccani online)

  • Sì, si scrive con l'apostrofo. Siamo di fronte a un caso di elisione, fenomeno che comporta la perdita della vocale terminale non accentata di una parola davanti alla vocale iniziale della parola successiva.

  • Questo (aggettivo e pronome dimostrativo) può elidersi davanti a parola che comincia con vocale sia al maschile (quest'anno; quest'ermo colle; quest'uomo; quest'ultimo), sia al femminile (quest'ansia; quest'epoca; quest'isola). Al plurale, l'elisione è meno usata se non rara; è di sapore antiquatamente letterario se la vocale iniziale della parola seguente è diversa dalla marca del plurale con cui termina questo (quest'impegni è ancora plausibile - ed è normale nella realizzazione orale; quest'amiche è ormai disusato e suona affettato).

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  • Josh, I like your answer, but it's difficult for me to upvote it. We have the best practice of answering in English to a question posed in English and in Italian to a question posed in Italian. Please, make an effort to translate the Italian citation into English or, at least, make a short English summary of it, to make sure that the OP would be able to fully understand your answer. – I.M. Jul 4 '15 at 10:39
  • @I.M. - well, OP has already made his choice and I don't think it can make a big difference now. Anyway thanks for appreciating my answer. – user519 Jul 4 '15 at 11:42

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