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Can this phrase ‘on one’s own’ be used as a post-modifying adjective phrase like below, meaning ‘while one is alone’?

The gangsters wanted to catch him on his own.

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Yes – Jon Hanna Jan 17 '13 at 11:22
"On his own" is a prepositional phrase, however, so it can't be an adjective phrase, only an adverbial phrase that functions as an adjective phrase. You can substitute an adjective for "on his own": The gangsters wanted to catch him {alone / red-handed}, which shows that the adjective and the adverb phrase have the same function, viz. to post-modify "him". Does it matter whether the phrase is an adjective or an adverb? If so, why? – user21497 Jan 17 '13 at 11:31
up vote 1 down vote accepted

Oxford Dictionaries Online define 'on one's own' as unaccompanied by others; alone or unaided. So, that also means 'while one is alone', as you have already guessed.

The gangsters wanted to catch him on his own (that is, while he was unaccompanied by others or while he was alone.

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