One of the things I learned in my 10 years of teaching grammar to undergraduates is that “it” is torture.

• For anyone paying attention that “it” is a lovely little nightmare known as an unclear pronoun reference. Am I saying that teaching grammar is torture or that learning grammar is torture? I left it confusing for effect, and because on any given day, it’s up for grabs.

While, it is true that occasionally  teaching is not fun, what I am referring to with that pronoun is learning grammar. Learning grammar, especially if you are doing it when you are older than middle school, is largely misery. And one of the primary sources for that misery is the ever-changing and oft loosely applied rules for certain elements of a sentence. One such monster? The relative pronoun.

• If you don’t know what a relative pronoun is, stop here and go study the section on the main Tongue Untied Web site.

Okay. Back to the point: Relative pronouns offer people struggling with grammar a special little brand of torture. At the top of the misery pyramid is trying to determine whether to use “who” or “whom,” but a close second is the confusion between “which” and “that.” Now, The Tongue Untied is willing to acknowledge that for, oh let’s say a half a millennium, people have used the two interchangeably, but we are not willing to admit that they are right.

We have rules here, and the one governing the use of “which” and “that” is as follows: Use “that” for introducing restrictive clauses and “which” for introducing non-restrictive clauses.

ARGH! Another grammar term. If you don’t know what a clause is, learn it here, but for the sake of moving this along, here’s a short primer. A clause has a subject and a verb.

The clauses using relative pronouns (i.e. who, whom, that, which) are dependent clauses. They need another clauses (usually an independent clause) to function. And the relative pronoun in the dependent clause is referring to a noun in the independent clause.

• The man whom they arrested was innocent. “whom” relates to (see how we get “relative”?) the “man.”

Okay. When the information in that dependent clause is essential (restrictive) to the meaning of the sentence (and we are not talking about people) then we use “that.”

• The hot dog that Ethan ate was spoiled. (we need that next clause to know just exactly what hot dog we are talking about.)

When the information in the dependent clause is not essential (non-restrictive) to the meaning of the sentence (and we are not talking about people), then we use “which.”

• Your new haircut, which is the best one you have had in years, makes you look like a movie star.

Learn the rule and you have averted yet another grammar disaster. Fail to and you have missed an opportunity to feel superior.

When writers set out to produce work, they are — in some sense — entering a minefield. Each word, phrase and piece of punctuation offers the opportunity for misstep. And while writing errors won’t kill you, the real possibility exists that they will kill your credibility.

Perhaps one of the most treacherous areas for writers is in word choice. The difficulty comes in the transition from speaking to writing. Words that sound alike or somewhat alike but are spelled differently can cause significant confusion when it’s time to write them down.

The following is a list of the top ten most commonly confused words.

1) To, Too, Two:

“To” is either a preposition or part of an infinitive (a verb before it’s conjugated).

* Preposition: The writers went to the author’s reading in hopes of learning something new.
* Part of the infinitive: Choosing to write for a living could be considered insane.

“Too” is an adverb, which means it needs an adjective or another adverb to modify.

* The writer spoke too quietly to be heard.

“Two” is a number.

* The writer submitted two different articles for the magazine.

2) There, Their, They’re:

“There” is used either as an adverb indicating place or an expletive.

* Adverb: The writers who have been published are standing there by the display.

* Expletive: There is one thing every writer must remember before submitting a query to a magazine: Know the publication.

“Their” is a possessive pronoun.

* Writers know that their success depends on hard work and perseverance.

“They’re” is the contraction of “they are.”

* They’re all successful authors, but their social skills leave a lot to be desired.

3) You’re, Your:

“You’re” is the contraction of “you are.”

* You’re one of the most successful authors in the country.

“Your” is a possessive pronoun.

* Did you meet your deadline?

4) It’s, Its:

“It’s” is the contraction of “it is.”

* It’s a well-known fact that a failure to proofread will come back to haunt you.

“Its” is a possessive pronoun.

* The magazine purchases its content from an on-line clearinghouse.

5) Accept, Except:

“Accept” is a verb. (to take possession of)

* The writers in my class sometimes struggle to accept constructive criticism gracefully.

“Except” is most often a preposition, meaning excluding.

* Everyone submitted an essay to the contest except you.

“Except” is, on occasion, a verb meaning to exclude.

* Will they except those writers from the list of participants.

6) Affect, Effect:

“Affect” is a verb meaning to influence.

* Good writing affects people in profound ways.

“Effect” is usually a noun meaning result.

* The effect of bad writing is also profound, but not in a good way.

“Effect” can also be used as a verb. It means to bring about.

* Talented investigative writers can effect dramatic change in their communities.

7) Than, Then:

“Than” is a conjunction used in a comparison.

* Do you think he is a better writer than you?

“Then” is an adverb indicating time (in the past.)

* I will edit your essay, but then I will expect you to do significant rewriting.

8.) Allusion, Illusion:

An “allusion” is an indirect reference to something.

* Using allusions effectively in your writing can be tricky for inexperienced writers.

An “illusion” is false impression.

* Using overblown words does not give the illusion of genius, but arrogance.

9) Allude, Elude:

“Allude” means to make an indirect reference to something.

* The writer alluded to mistakes made by the editor when explaining his rejection letter.

“Elude” means to escape or avoid detection.

* Not even the best writer can elude making an error at some point.

10) Elicit, Illicit:

“Elicit” is a verb meaning to bring out or draw forth.

* Her essay on prison reform elicited a strong reaction.

“Illicit” is an adjective meaning illegal or unlawful.

* The author’s illicit copying of her assistant’s work led to her downfall.

As with all errors, the best protection against their making it into print is proofreading. But given how easy they are to confuse, consider using the search command in your writing program to find them and then confirm that you have used the correct option.

I have decided to begin a new series of posts entirely dedicated to the little BUT IMPORTANT elements of English writing that seemed to have disappeared from the K-12 system

I am starting with “if” and “whether” not because I think it is the most important, but because I read yet another article in the New York Times today where “if” was used incorrectly and writing about it seemed better than having my head explode.

First, the basics:

Use “if” to express a condition.

• CORRECT: Comments are moderated and generally will be posted if they are on-topic and not abusive.
• WRONG: I don’t know if he’s ready for my New York game.

Use “whether” to express alternatives.

• CORRECT: Many of the assembled are questioning whether he is conservative enough.

• CORRECT: Their six-month truce comes to an end today, and neither is sure whether to renew it.

• WRONG: The officer told the investigator he was not sure if he fired his weapon.

Use either “if” or “whether” with:

1) Indirect questions.

No one knows for sure whether/if Iran has the rest of the components needed for a bomb.

He’s not sure whether/if he’s scored enough points with Santa to be getting one of those in his stocking.

2) Yes / No questions.

He wasn’t even sure if/whether he did any good.

She could not remember if/whether he brought his coat.

Clearly, it is not simply a matter of knowing the rules or more people would get it right. So, let’s get geeky and try to tattoo this on the grammar sections of our brains.

Be advised! We are heading into grammar term territory.

1) After a preposition, use “whether.”

If you don’t know what a preposition is, hop over to our grammar site and have yourself a bit of study. If you have a general sense of the little buggers, then you are ready to follow the rule: preposition + choice of  “if” or “whether” = “whether”

• CORRECT: For actions on a site that might be considered private, shouldn’t users have the choice about whether to make them public?
• CORRECT: The test for whether such internal loans make economic sense is exactly the same as the test for external loans.
• WRONG: “Batman is Batman, regardless of if Bush is in the White House or not,” he said.

2) Before infinitives, use “whether.”

Same first step, if you don’t know what infinitive are, study on them here.

• CORRECT: The clinic workers, who have been detained for two months while authorities decide whether to charge them, deny that they did anything wrong.

But don’t be misled into using “whether” rather than “if” preceding an infinitive if the “if” is part of the conjunction “as if.”

• EXAMPLE: As if to ward off the mayhem outside, the soldiers have held to some military rituals.

You would have gotten that on your own, right? Really, how incoherent would the sentence be? “As whether to ward off the mayhem outside, the soldiers have held to some military rituals.”

3) When the sentence contains a two-part option with “or,” use “whether.”

• CORRECT: The captain said he could not remember whether they had asked for the money or demanded it.
• CORRECT: They were asked whether they had modified their views as a result of their visit to the Soviet Union
• WRONG: It’s not clear if they simply failed to consider the privacy implications or thought about it and decided it didn’t matter.

4). If the “alternatives” lead the sentence, use “whether.” In other words, if instead of being connected by “or” the two-part option begins the sentence, you still use “whether.”

• CORRECT: Whether they spoke for Progressive or reactionary candidates, they took the view that the incumbent was out of it.
• WRONG: Asked if the rabbit in cream sauce could be split in half or must the kept whole, the waiter shrugged.

5) When the clause containing the “option” is a subject or a predicate nominative, it’s best to use “whether.” (”If” is acceptable in some circumstances but not preferred so why risk it?)

• CORRECT: Henry is certainly a capable chef, but whether he can master the intricacies of Vietnamese soup is another question.

(”Whether” is the subject of the verb “is.”)

• CORRECT: The question is whether I buy a TV or something more important.”

(”[W]hether I buy a TV” is the question and the question is “whether I buy a TV.” They are connected by a linking verb, making the “whether” clause a complement/predicate nominative. Do I need to tell you again to go the Web site if you don’t know the parts of a sentence?

• WRONG: The question is if the lingering bitterness from the port deal is going to outweigh the stretched hand of needy institutions.

Okay. That’s enough of that. Best of luck out there.