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I'm currently practising for the TOEFL so I'd really like you to tell me the correct answer for the following question with a brief explanation.
"I spoke to him kindly ...... him."

a) not to frighten
b) so as not to frighten
c) in order to not frighten
d) for not frightening

Only one is correct, so I'd choose a) but nevertheless I actually think d) is possible as well, even though a) sounds better. Since it's just my feeling that tells me to choose either a) or d) I'd appreciate rules eliminating the other options.
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Comments  (Page 2) 
Thank you very much! I have been completely unfamiliar with the the form "so as (not) to"... I'll keep it in mind for the TOEFL, though! Emotion: wink
Cool Breeze So as normally emphasizes an infinitive. So does in order, but in c) not is in the wrong place. In order not to frighten would be correct.
Tell that to Faulkner or to Shaw (who was quite outspoken about it):Emotion: smile

As I've already mentioned somewhere else here:

Faulkner on Tennyson (in "Light in August"):

It is like listening in a cathedral to an eunuch chanting in a
language which one doesn't even need to not understand.

Students: Are you brave enough to let our tutors analyse your pronunciation?
I agree the "in order to" meaning/usage is quite alive in and well for "so as," including in AmE.

I'm just reporting what M-W is saying.
Just to be 100% sure:
Is it correct to say "I did my homework so as to please my parents."
And is this really the most popular and best way to express it? I'm just a bit confused because I haven't heard it at all so far.
I did my homework to please my parents.
would be simpler and accepted by many more, IMO.

E.g.:
----
Children also completed questionnaires about their motivations such as
what they liked about the topics and not just on whether they were
doing homework to please
their parents.

http://clearlyexplained.com/news/nature/2005/mar/1N1503_2005.html
Students: We have free audio pronunciation exercises.
Why not remove the "so as" from the sentence?

"I did my homework to please my parents."
Which I did (I had the old version in mind when editing)Emotion: smile
Yeah, surely you could put it that way but what's the point in the "so as (not) to" form, then? Is it only used in negative sentences? I don't get why "I did my homework to please my parents" is correct (I know that the sentence is perfectly ok) whereas "I spoke to him kindly not to frighten him." is incorrect...
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Hi,

In his Practical English Usage, Michael Swan discusses 'so as to . . .' in his section on 'Infinitive of purpose'.

He says that the following all express the same idea.

He stopped for a minute to rest.

He stopped for a minute in order to rest.

He stopped for a minute so as to rest.

Personally, I consider that the last two usually add more emphasis to the meaning, and also better style.

Swan also notes that in negative sentences, the infinitive alone (eg he left early not to be late) is usually not correct. Correct would be

He left early in order not to be late.

He left early so as not to be late.

Best wishes, Clive

PS - While I agree with the bold portion, I think the following quote is in other ways an example of poor English and, as such, liable to confuse learners.

Children also completed questionnaires about their motivations such as
what they liked about the topics and not just on whether
they were
doing homework to please
their parents.
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