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This is a broad request for tips, but I have a specific question in mind as well.

尽 can be pronounced as "jin4" or "jin3".

In Pleco, the definition for "jin3" is "to the greatest extent" while one of the definitions of "jin4" is "to the utmost; to the limit".

Perhaps this is a translation issue, because to me, these 2 definitions are essentially the same. Based on this, I still have no way of knowing when the character is jin4 or jin3 when it means "to the utmost" or "to the greatest extent".

Is this just a brute force memorization problem or are there some tips for figuring out when to pronounce it one way & when to pronounce it another?

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You mean heteronyms? –  deutschZuid Aug 25 '12 at 21:53
    
Can you call them that in Chinese? There's no spelling so they can't really be spelled the same. I mean characters that are written the same but have different pronunciations depending on the context, meaning, etc. –  aelephant Aug 26 '12 at 1:21
    
Same concept really. –  deutschZuid Aug 26 '12 at 2:01
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Looks like you're right after all. A Google search for "define:heteronym" only mentioned spelling, but on Wikipedia they say: "In linguistics, heteronyms (also known as heterophones) are words that are written identically but have different pronunciations and meanings." Since 多音字 are written identically, I'd say they fit the bill. –  aelephant Aug 26 '12 at 2:52
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2 Answers 2

To answer your specific question, it should be kept in mind that 尽 is a simplified character that merged both traditional characters 盡 (jìn) and 儘 (jǐn), which is why it appears to be a 多音字 in Simplified Chinese. The difference between 盡 and 儘 is very subtle though. This link talks about the difference as it applies in Cantonese, but I believe it applies in Mandarin as well:

「儘」是「力求達到最大限度」,強調的是「力求」,至於能否達到「所求」,不得而知。「盡」則有「達到最大限度」的意思,強調達到。

儘 is "strive to attain maximization", with the emphasis on "strive"; whether it can be attained is unknown. 盡 on the other hand has the meaning "attain maximization", with the emphasis on attaining.

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Ah, very interesting! I had no idea it was 2 characters merged into 1. –  aelephant Aug 26 '12 at 1:19
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Baidu has a very good article on this topic.

多音字有以下几种用法:

  1.读音有区别词性和词义的作用。这种类型的多音字在文言文中叫做“破音异读”,约占到全部多音字的80%。对这类多音字,我们应该根据不同的读音加以辨析、记忆。如“将”:jiāng(可作动词或副词等),动词可作“带领”解,副词可作“将要”解;jiàng(名词),作“将帅”或“大将”解;qiāng(动词),作“愿”“请求”讲,如“将子无怒”(请你别生气)。

  2.使用情况不同,读音也不同,读音有区别用法的作用。如“薄”:báo,不厚的意思,一般单用,薄饼、薄纸;bó,一般用于合成词,薄礼、厚古薄今;bò,薄荷(专有名词)。

  3.语体不同,读音不同,读音有区别语体的作用,主要体现为口语和书面语等。如“给”:口语读gěi;书面语读jǐ,给予、给养。

  4.方言词汇的存在造成多音。这类多音字比较少,仅限于部分地区。如“忒”:tè,差忒(差错之意);tuī(方言),风忒大、房子忒小(忒:太)等。

  5.文言文中的一些通假字延续使用到现在而形成了多音字,普通用法和人名地名等用法不同而造成多音等。(此部分详见第二节“异读字”。)

The author of the article recommends using a classification technique to help remember the different pronunciations of 多音字. This boils down to identifying such characters (about 600 of them in 《新华字典》), organising them into different groups, and learning them by heart. The important point is to simplify the task by dividing it into smaller tasks and tackling them one at a time.

In summary, there is no short cut except practising and more practising.

With regards to your specific question, I don't have an answer to that. Based on my own experience, jìn is used on most occasions. In some cases such as 尽可能 and 尽量, however, they seems interchangeable, though the meaning is exactly the same. Perhaps it is a matter of emphasis?

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Good point about the interchangeability. I asked 3 of my Chinese coworkers & they repeatedly said that 尽快 is pronounced "jin4kuai4" while my dictionary says it should be jin3kuai4. This reminds me of the controversy surrounding 下载. –  aelephant Aug 25 '12 at 8:07
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