The Manhattan GMAT Sentence Correction book says that
Although I take frequent naps, I study effectively
is correct, while
I study effectively although taking frequent naps
Why is the second sentence wrong ?
Rachel, a senior member at thegrammarexchange, says:
While it is possible to construct sentences in this way [although + verb-orientated ing-form], they often seem heavy, and are, indeed, an older style. There are some, though few, in the New York Times archives, a lot of them appearing in the years around 1900! Among the following examples, a few are more current....
• Mr. Draskovic, although speaking for many ordinary Serbs, especially here in the capital, is not ''inside the system.'' He said he joined the Government in ...
• although living in a large villa she had been leading a life of comparative poverty, rarely receiving visits apart from a few intimate friends who, ...
• Let's accept that explanation for the sake of argument (although, knowing fans as I do, Clemens might very well have received an ovation). ...
• although, having said that, I think I'm in denial that I am doing it now. Regardless, I think it's a matter of a person's physical condition ...
• The trial must proceed slowly, because the Duke, although having lived in the United States for sixteen years, cannot understand the English language. ...
• although having had many narrow escapes, he was never seriously wounded up to this period. He passed through the eight days' battles in the Wilderness in ...
The examples not containing parentheticals after the 'although' can be seen as deletions, eg
Mr. Draskovic, although he is/was speaking for many ordinary Serbs, especially here in the capital, is not ''inside the system.'' He said he joined the Government in ...
(Those with parentheticals after the 'although' are not the same structure.)
Note that the noun-orientated ing-form is often used after 'although':
Although taking a bath immediately after eating is usually not too serious, it is unwise.
Although the taking of a bath immediately after eating is usually not too serious, it is unwise.
Shoe points out that 'Rachel' (quoted above) later says that she finds
Although throwing the ball as high as he always does, he doesn’t get much admiration from the girls.
Shoe (in a comment) then suggests that "the 'although + present particle' construction works for stative verbs or durative verbs, but not punctual/punctive verbs". This last example is iterative, just to complicate the analysis. I'd say that the present participle isn't the usual choice for a one-off punctive occurrence whether or not 'although' precedes it. But I can find nothing wrong with
Will Scarlet, although hitting the target, was disqualified for using the wrong colour of arrow.
And addressing Araucaria's point, I'm not sure if one should consider the two events in this example as having the same time-frame or not. I'd agree that some examples sound less acceptable than others, but I think this gets rather complex.
I think a misplaced modifier (ref:MGSC, page 65):
Modifiers are phrases that modify another part of the sentence. In order to be correct, the modifying phrase must be as close as possible to what it modifies.
with 'frequent naps` modifying the student's study pattern. Which makes the first sentence correct over the second.
Also I don't think the second sentence is complete - we could easily extend it:
I study effectively although taking frequent naps does slow me down
I study effectively although taking frequent naps is often frowned upon by others.
to mean different things. And page 62 states:
Some answers to GMAT questions are grammatically correct but change the meaning of the sentence. Such answers are wrong.
The second sentence needs "despite" or at least that is what I was taught. They are both used to show contrast and have the same meaning. The only difference is the way they are used;
After "although" you need a "subject + verb".
Although it rained a lot, we kept playing.
After "despite" you need a "noun, a pronoun or -ing".
Despite rain, we kept playing.
I am not really sure but this might be the case because "despite" is a noun whereas "though" is an adverb (I take "although" and "though" are %100 same though they are not).
My Answer is that You should say...
I study effectively although **I take** frequent naps.
I have a few other possible answers.
In the correct version the structure consists of:
I take, I study
In the incorrect version the structure consists of:
I study, Taking
For the "both true or both untrue" idea to work both sentences would need to have the same sentence structure to be reversible.
This may also be a possible solution.
I study effectively, although taking frequent naps.
( I'm not sure if this is correct unless the sentence continues after "naps" to define the reason for the naps ). For example:
I study effectively, although taking frequent naps to rest.
My last possible answer...
I study effectively. Although, taking frequent naps.
"I study effectively." can stand on it's own, hence the comma could become a period. The statement is Followed by an expansion on a possible reason for the sentence to be deemed untrue. ( hinting that there may be a more "effective" way to study since they could possibly study better if no naps were taken.)showing contrast to what they said and what they or others may think. @Araucaria
The sentence " I study effectively although taking frequent naps." is wrong because, the word "taking" does not specify who or what is taking or being taken so cannot be separated with a comma or an incomplete sentence would be formed.
To fix this two things must be changed. first the word "taking" should be changed to "I take" and then a comma will need to be added to separate the newly formed sentences from each other.
The correct way to write the sentence would be "I study effectively, although I take frequent naps." @sumelic @raffamaiden