Question

1. lose: to not win a game, argument, or election
2. lose: not to win a game, argument, or election
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Which one is right? Are both okay?
Is 'to not win' a split infinitive? Not is an adverb, right? What does 'not' modify in #1? What does 'not' modify in #2? What is the difference in meaning because of the position of 'not'?

Answer 1

Since it's usually better not to split an infinitive with an adverb or anything else, the second one is far better phrasing (word order).

The infinitive in your definition is "to win" -- and putting the adverb "not" before the infinitive makes smoother phrasing.

Yes, "not" is the adverb, and it's modifying the infinitive, "to win."

Answer 2

1. lose: to not win a game, argument, or election
2. lose: not to win a game, argument, or election
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Thank you for your help.
In #1, 'not' modifies 'win' and in #2, 'not' modifies 'to win'.
Am I right? And do you mean there is no difference between them?

Answer 3

There is no difference in what "not" modifies. The entire infinitive is "to win" -- and "not" modifies the infinitive.

Answer 4

"not" modifies the infinitive verb "to win" in both. It's the placement of the adverb "not" that's at issue. It's better "not to win" instead of in the middle of the verb "to win".