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We can use as a substitute in successive sentences for something we've already mentioned so that we don't need to keep saying what it is:

  • どのTシャツが好き? → 赤いが好き。

Then there is the possessive/associative の:

  • 家の屋根、空の鳥、etc.

I was telling my friend about a new wallet I bought. By implication (or obviousness), it means the wallet I had before is now the "old wallet". So I wanted to talk about the contents of the old wallet. Can I use these two s consecutively to describe them, like:

  • 古いの の 中身

Is this grammatical? Used? Or would it be better to just say 古い{財布・もの・やつ}の中身?

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The first の is the pronoun の.
The second の is the genitive の.

There are two possible sequences of these two のs:

  1. genitive + pronoun:  この本は花子のだ。 "This book is Hanako's."

  2. pronoun + genitive:  赤いのの表紙 "the cover of the red one"

In the former, the sequence of two のs is ungrammatical; you have to delete one of them.
In the latter, the sequence of two のs is okay.

(Examples adapted from a draft version of Hiraiwa's Constraining Doubling, although there are a number of publications on this subject--see the references section of the linked paper for further discussion.)

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  • Can you say この本は花子のんだ though? – ithisa Jan 18 '14 at 2:20
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    Hiraiwa says some speakers use んの or のん, in which case deletion doesn't occur. I take this to mean that you should avoid the のん version in standard Japanese, though the paper doesn't say so explicitly. – snailplane Jan 18 '14 at 2:24
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    ~のん sounds childlike to me. (幼稚園児か、小学校低学年くらいの・・・でも、近年はあまり聞かない気がする・・・古い言い方なのかも) – user1016 Jan 24 '14 at 6:37
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    @Chocolate ええこと言わはるわ。むっちゃ懐かしい響きや。確かに最近聞かへんな。 – l'électeur Jan 24 '14 at 8:38
  • @TokyoNagoyaさんは東京と名古屋火傷、関西弁なん? – istrasci Jan 24 '14 at 15:36

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