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He does not ride a bike wearing a helmet.
Or
He rides a bike not/without wearing a helmet.
Second sentence
He doesn't cross the road while talking on mobile
Or
He crosses the road while not talking on mobile.
Is there any difference between these two sentences?
Actually someone asked me this question and I couldn't find any suitable answer. Can you guys help me?
He doesn't ride a bike whilst wearing a helmet.
Means that either he doesn't ride a bike at all, or that whenever he does ride a bike, he doesn't wear a helmet.
He rides a bike without wearing a helmet.
Means that he does ride a bike, but whenever he does so, he doesn't wear a helmet.
He doesn't cross the road whilst talking on a mobile ('phone).
Means that either he doesn't cross the road at all, or that whenever he does cross the road, he doesn't talk on a mobile.
He crosses the road whilst not talking on a mobile ('phone).
Means that he crosses the road only so long as he's not talking on a mobile.
As you can see, if you say "He doesn't ride a bike whilst wearing a helmet" it's somewhat ambiguous as to whether you're referring to the whole action of "riding a bike whilst wearing a helmet" or merely to the second part. If you want to make it clear that he might sometimes ride a bike, but never with a helmet on, you'd be better using the second form - "He rides a bike without a helmet" - or changing the order around, "He doesn't wear a helmet whilst riding a bike."
