Disclaimer: I don't work on the Office team.
Word has a smart quotes feature where it will automagically transform
straight "double quotes," 'single quotes,' and greengrocer's apostrophes
curly “double quotes,” ‘single quotes,’ and greengrocer’s apostrophes
as you type. You send a Unicode Character 'APOSTROPHE' (U+0027) to Word, and Word turns it into a Unicode Character 'LEFT SINGLE QUOTATION MARK' (U+2018) or a Unicode Character 'RIGHT SINGLE QUOTATION MARK' (U+2019) as appropriate. If you type it at the beginning of a word, it's an opening-single-quote; if you type it in the middle of a word, it's an apostrophe; if you type it at the end, it's either an apostrophe or a closing-single-quote, but both are the same character, so it doesn't matter.
The apostrophe is occasionally used at the beginning of a word, to mark elided letters. Word has trouble with this.
‘Twas brillig, and the slithy toves did gyre and gimbol in the wabe.
I want to give the Word folks credit here. A common use of an apostrophe at the beginning of a word is to abbreviate a year. Word gets this right (I'm using Word 2010 with default settings:)
Check it out: a ’57 Chevy!
But Word also gets it wrong when you want to single-quote a clause that begins with a number:
singing ’99 bottles of beer on the wall’.”
Also, if you pluralize the date, Word gets suckered:
’10 models on sale! Check out the new ‘11s!
Little nifties, from the ‘50s, innocent and sweet;
Sexy ladies from the ‘80s, who are indiscreet
-- 42nd Street
For those times when Word gets it wrong, here's how to fix it.
If you want to type a word that starts with an apostrophe:
- Type the apostrophe. Word assumes you want an opening quote. Fine
- Type the apostrophe again. Word shrugs its shoulders and gives you a closing quote in a little soixante-neuf of punctuation.
- Type the magic sequence:
- Left arrow
- Right arrow
- Et voilà. Continue typing your word.
If you want to use an opening single quote with a sentence that starts with a number:
- Type the opening quote and the number in its entirety. So far, so good.
- Type the word breaker (usually a space.) Word "helpfully" turns the opening single quote into an apostrophe.
- Invoke "Undo" via your favorite mechanism (I prefer Ctrl-Z since I'm already on the keyboard.)
- Et voilà. Continue typing your quoted clause.
‘99 bottles of beer on the wall
That "Undo" tip is actually a fairly powerful curative against all sorts of Word voodoo.