how to know whether to is a preposition or marks the infinitive

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In the following examples, I'm quite sure "to" is a preposition.

I'm used to having more time to complete exams.
I look forward to having more time to complete my exam.

In this case, I'm not so sure.

I'm entitled to have/having more time to complete my exam.

I wrote having but was told that's incorrect. What makes the third example different from the first two examples?
Is it a matter of memorizing and internalizing the difference or is there an element I'm not seeing that separates them?
Thanks.

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@perennialloner,

I'm used to having more time to complete exams.
I look forward to having more time to complete my exam.
In your first two sentences, the first 'to' is followed by the gerund 'having' and is therefore a proposition; 'to complete' is the infinitive.

I'm entitled to have/having more time to complete my exam.
In this sentence, 'entitled' should be followed by the infinitive ('to have). 'Entitled to having more time' is wrong. 'To complete' is the infinitive as before.

Quote:

Is it a matter of memorizing and internalizing the difference or is there an element I'm not seeing that separates them?

You can try to remember that 'to' followed by a verb form ending in -ing does not make an infinitive. The infinitive of a verb consists of 'to' followed by the 'base' version of the verb (the version found in a dictionary).

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@contrex,

contrex wrote:

In your first two sentences, the first 'to' is followed by the gerund 'having' and is therefore a proposition

That should be 'preposition'.

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@contrex,

Quote:

You can try to remember that 'to' followed by a verb form ending in -ing does not make an infinitive. The infinitive of a verb consists of 'to' followed by the 'base' version of the verb (the version found in a dictionary).

Thanks for responding. I meant to ask if there's a way of knowing when "to"is a preposition without knowing the verb that follows it.

With "I'm entitled to have," how am I supposed to tell it's have and not having?

Thinking on it, "I am used" + "to" as a preposition seems like the exception, while the "I am entitled" + "to" as an infinitive marker seems more common. I am interested to, I am excited to, etc...

I wondered what makes the two different from each other that informs the way "to" acts.

Hopefully that makes sense.

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@perennialloner,

perennialloner wrote:

With "I'm entitled to have," how am I supposed to tell it's have and not having?

By memorising/absorbing that when 'entitled' is followed by a verb, that verb must be in the infinitive, as are other similar verbs - allowed, forbidden, permitted, encouraged, required etc.

Quote:

Thinking on it, "I am used" + "to" as a preposition seems like the exception, while the "I am entitled" + "to" as an infinitive marker seems more common. I am interested to, I am excited to, etc...

I wondered what makes the two different from each other that informs the way "to" acts.

Usage makes them different.

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For any verb, you can use a dictionary; many are available via Google:

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@contrex,

Thank you very much.

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how to know whether to is a preposition or marks the infinitive

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