[Grammar] relative clauses

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Dinusha

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Sinhalese
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What is the grammatically correct clause mentioned below ?

1.(a) Isobel,whose brother john was,(had heard the joke before.) or
(b)Isobel,whose brother was john,(had heard the joke before.)

2.(a)John,who Isobel's brother was... or
(b)John,who was Isobel's brother...
 
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1a and 2a are wrong; totally unnatural.
1b and 2b are grammatical, but are strange in the context. Another way of saying this is:
"Isobel, John's sister, had heard the joke before." This is far more natural; it just identifies who Isobel is, for those who don't know
Isobel, but who do know John. For this reason, 2b is better than 1b.

Thanks for taking my other advice. :-D It doesn't always happen.
 
I think it may have something to do with 'he' being a pronoun.

Not a teacher.
 
I don't like it much. But it depends on the context. That sentence also uses 'he', not 'John'. So, something must have been said about John - given that he is referred to as 'he', and that 'he' is understood as John.
This is possible:
"John told a very funny joke. Isobel, whose brother he was, had heard the joke before and did not laugh."
But far more natural would be: "Isobel, his sister, had heard the joke before..."

Dictionaries often offer examples that sound unnatural because they're given without a context. But I'm still trying to think of a natural context for "Isobel, whose brother he was, ..." Perhaps another native speaker can think of a natural context.
 
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