Tell me please what is the difference between the following sentences.

1 "Mike is going to sing at night."
2 "Mike is going to sing on the night."

Actually I thought that the preposition "at" have to be used before the word "night", but I have recently come across " on the night", so I am confused.

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    Could you give any examples of "on the night" you have found? As a native speaker, it's not a common phrase and I imagine would tend to be found in literature more than speech. EDIT: Or is "on the night" in the context of "he is going to sing on the night of the 20th January?" – Bilkokuya Jan 19 '18 at 16:37
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    @bilkokuya I interpreted the question as such as well in my answer. Unless the OP is studying archaic phrasing, I wouldn't expect them to see that wording. – Jakob Lovern Jan 19 '18 at 16:46
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    on the night on its own does not exist. – Lambie Jan 19 '18 at 17:53

The second sentence, 'Mike is going to sing on the night,' can't be used on its own, but it's still correct.

In English, we usually use 'on the night' to describe a specific night. Of the various examples I could use, there are a few basic forms:

Implicit Specification

Mike is actually a target for an assassination attempt by a terror organization. In all their correspondences between each other, they refer to 'the night,' though it's never stated that 'the night' is when they execute their plan (and Mike.)

In this case, sentences that refer to 'the night' are implicitly assumed to mean that night.

For example:

Remember that Mike will be singing on the night. We need to take him out on stage.

Inferred Specification

If, in a previous sentence, 'the night' is identified, then the value is used by inference. @Billy Kerr provided an excellent example of this in the comments:

The concert will be held on Friday evening. It's going to be wonderful. Mike will sing on the night.

In this case, 'the night' refers to Friday evening.

Extended Literal Specification

Maybe the sentence you provided wasn't complete. If I were to complete it, I'd expand it to something like:

Mike is going to sing on the night of the 25th

This explicitly describes which night Mike will sing on within the scope of the sentence.

This usage could be better viewed as an extension of 'on the (date)'. One would logically say

Mike is going to sing on the 25th

which describes when Mike will sing. If we prepend 'the night of' to 'the 25th', then we talk more specifically about when Mike will sing.

Noun Form

If 'On the Night' is the title of a song, then Mike would be singing that song.

In conclusion

You can't use that grammar without the understanding that 'the night' refers to something specific.

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    No! The second sentence is not "grammatically incorrect"! It's a perfectly natural construction in contexts where the night is a specific known upcoming night. Consider the stereotypical theatre director saying: It'll be alright on the night (there will be a specific night when his play will be performed live, and that's what he's referring to). In OP's example the speaker might mean that although some other "stand-in" sang in the rehearsals, Mike will be the one singing on "Opening Night". – FumbleFingers Reinstate Monica Jan 19 '18 at 18:11
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    Oh, oops. I forgot about context dependent wording. Thanks for reminding me! I'll update my answer to include that. – Jakob Lovern Jan 19 '18 at 18:19
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    I'm afraid I don't think it's fair to say on the night is "grammatically weird" either! It really is perfectly natural phrasing for contexts like my example (or indeed, OP's example, if the speaker is referring to a specific night that the audience already know is the contextually-relevant night). – FumbleFingers Reinstate Monica Jan 19 '18 at 18:26
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    Now with formatting! And quotes! And secret murder plots! – Jakob Lovern Jan 19 '18 at 19:07
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    ...I think the bottom line is you still don't like the construction for reasons of your own, but I assure you it's perfectly natural English. – FumbleFingers Reinstate Monica Jan 20 '18 at 16:11

at night refers to the time of day.

Some animals leave their burrows at night.

It is a general term.

the night can be used in a similar way, to refer to the time of day in general terms.

She said she was a nocturnal animal, and that she loved the night.

But when we put the preposition on in front of the phrase, it can acquire a variety of meanings, as Jakob has ably set forth in his answer.

To those meanings we can add the meaning of "about" for on:

We are going to hear a talk by a leading environmental critic of light-pollution. His talk is entitled On The Night.

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