Defining words syntactically
One way that people have attempted to define words is to call them the smallest unit of syntax. This seems reasonable: sentences are built by combining words according to particular patterns. But even this simple definition runs into problems. Take a sentence like the following:
(1) Harry coughs every time he steps outside.
Everyone would agree that Harry, every, and outside are words, and that -s is not. But at the same time, some people (though not all) would argue that -s is indeed a unit of syntax and that it occupies a particular position in a syntactic tree. The following diagram illustrates how we might break cough off from -s syntactically:

Calling words the minimal units of syntax raises the question, “What is syntax?” If we think of syntax as the component of the human grammar that governs the ordering of items, then -s should be a word. After all, it is subject to ordering principles. It must follow cough; we don’t say s-cough. If we respond by saying that syntax governs the ordering of not just any item, but only words, then we are back where we started. What is a word?
Another characteristic of words is that they are the smallest unit of language that can stand alone:
(3) When are you going to the store? Tomorrow.
What did the emperor wear to the procession? Nothing!
We recognize the ability of words to stand alone by saying that they are free forms. Units that are incapable of standing alone, such as affixes, are correspondingly called bound forms. This characteristic of words also runs into problems. Certain forms that native speakers would identify as words are not capable of standing alone and therefore do not meet this definition:
(4) Whose book is this? *My.
My is a word, as we would all agree. But it generally does not stand alone.1 The reasons why my cannot stand on its own have more to do with syntax than with morphology: it is a determiner, and it generally appears alongside a noun. Speakers would use mine in this context instead. Nevertheless, this example shows that a potential diagnostic for wordhood – can it stand alone? – is not universally reliable.
Once in a while we even get a supposedly bound form appearing on its own. In the musical Camelot, Queen Guenevere sings the following lines:
(5) It’s May, it’s May, the month of “yes, you may”
The time for every frivolous whim, proper or im …
When all the world is brimming with fun, wholesome or un-
The prefix im- is used on its own to rhyme with whim, and un- is used to rhyme with fun. We are dealing with a creative word play here. Both im- and un- are stressed here, which means that in some sense, the song writer has turned them into words. We are not proposing otherwise. We present this example to help demonstrate that words are difficult to define, and that traditional notions such as bound and free are not always reliable.
1 One exception is in first language acquisition. Some children use my in this context before acquiring mine.