The use of If and When

We use “if” when you have a conditional sentence and “whether” when you are showing that two
alternatives are possible. In informal writing and speech the two words are often used interchangeably.

1. Michele didn't know whether Obama would arrive on Friday.

2. Michele didn't know if Obama would arrive on Friday.
In either sentence, the meaning is that Obama may or may not arrive on Friday.

Now, here are some examples where the words are not interchangeable:

1. Michele didn't know whether Obama would arrive on Friday or Saturday.

Now see how the sentence has a different meaning when I use if instead of whether:

1. Michele didn't know if Obama would arrive on Friday or Saturday.

3. Call Loyd if you are going to arrive on Friday.
4. Call Loy whether or not you are going to arrive on Friday.

The first sentence is conditional. Call Obama if you are going to arrive on Friday means Aardvark
only needs to call if he is coming.

The second sentence is not conditional. Call Obama whether or not you are going to arrive on Friday
means Aardvark needs to call either way.

To sum up, use whether when you have two discrete choices or mean "regardless of whether," and use
if for conditional sentences.

Now in addition to arriving on Friday or Saturday, it's possible that Aardvark may not arrive at all. These
last two sentences show why it is better to use whether when you have two possibilities, and that is why
I recommend using whether instead of if when you have two possibilities, even when the meaning
wouldn't change if you use if. It's safer and more consistent.