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1. I don’t know who John won’t criticize, but I have a good idea about who he will

2. I don’t know what Bill should be proud of, but I know what John should.

3. What should Bill be proud of, and what should John?

4. I don’t know who won’t be fond of this book, but I know who will.


Thank you.

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Nananara

1. I don’t know who John won’t criticize, but I have a good idea about who he will.

2. I don’t know what Bill should be proud of, but I know what John should.

3. What should Bill be proud of, and what should John?

4. I don’t know who won’t be fond of this book, but I know who will.

All OK, but note that sentences with these patterns are not very common. They are somewhat awkward with 'should'.

CJ

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Nananara

1. I don’t know anyone that/ who John won’t criticize, but I have a good idea about who he might be.

2. I don’t know what Bill should be is proud of, but I do know what John should.

3. What should Bill be proud of, and what should John? This is a bad sentence.

4. I don’t know who won’t be fond of this book, but I know who will. This one is bad as well. One one hand, you said "you don't know" but in the second clause, you said " but I know who will".

In the context of "I don't know who...", it usually continues with present simple. So the sentence should be" I know know anyone who is not proud of his xxxxxxx".



Thank you.

Thank you so much.

Hi, CJ-san.

Thank you so much. Yes, they are very odd and unnatural, I think. But, grammatically, maybe OK.

Then, 'should' is bad. If so, 'might' is better like below?

2'. I don’t know what Bill might be proud of, but I know what John might.


By the way, how about this below?

2". I don’t know what Bill should be proud of, but I know what John should be.


Of course, this is also very odd, and 'should' is used, but I think this is grammatically better than the original (2).

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Nananara

Hi, CJ-san.

Thank you so much. Yes, they are very odd and unnatural, I think. But, grammatically, maybe OK.

Then, 'should' is bad. If so, 'might' is better like below?

2'. I don’t know what Bill might be proud of, but I know what John might.


By the way, how about this below?

2". I don’t know what Bill should be proud of, but I know what John should be.


Of course, this is also very odd, and 'should' is used, but I think this is grammatically better than the original (2).

Both 2' and 2" sound a bit off. I think most people say the whole phrase in such cases.

2' ... but I know what John might be proud of.
2" ... but I know what John should be proud of.

It seems to me that most of these echo-type phrasings involve do, can, or will.

I don't know, but I know someone who does.
I don't know if somebody else can do more, but I know I can't.
I don't know how you'll vote in November, but I know how I will.

CJ

Thank you so much.