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Suppose I am an event organiser and while conducting a game I announce that - "Whoever wins this game, I will get him a chocolate".

Here I used the word 'a chocolate' so does it mean 'one chocolate' or 'any chocolate' or 'more than one chocolate' or 'anyone chocolate' ?

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In fact, when you say "a chocolate", mainly it means a single piece of chocolate, because the function of the indefinite-article in this specific case is to denote that it's singular.

I'm saying "in this specific case" because the word "chocolate" is sometime uncountable and the it refers to any kind of chocolate as a general title. see below.

enter image description here

You don't need to say "a chocolate" in order to refer generally to any kind of chocolate, because chocolate by itself (without indefinite article) does it already.

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It is more correct to say:

  • Whoever wins this game gets a chocolate bar.

This accounts for multiple winners and genders, and specifies it's a chocolate bar, and not say a bonbon.

If you only want the first winner, then say:

  • Whoever wins this game first, gets a chocolate bar.
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A chocolate only ever means one of three things: a chocolate sweet, individually wrapped; a chocolate sweet, unwrapped, which came from a cheap packet; a drink of chocolate.

The wrapping might be in a twist of metalicky, plasticky stuff and it might be in an individual depression in a blow-molded plastic tray; that matters little.

A chocolate is never the same as a bar of chocolate nor a piece broken from a bar…

By the way, supposing you really were an event organiser, there is no possibility you would say that

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It means 'one chocolate', i.e. the item shown in the top-left of the picture below.

enter image description here

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