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The pronunciation of 吏 (lì) is frustratingly hard to remember since it's different to two similar-looking characters 史 (shǐ) and 使 (shǐ). Sometimes learning the etymology, and the reason why a character is pronounced a certain way, can make it easier to remember how to pronounce. Googling gave me this, but I didn't immediately find anything about pronunciation.

Question: Why is 吏 (lì) pronounced differently to 史 (shǐ) and 使 (shǐ)?

3 Answers 3

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Let us look at the reconstructions (specifically, at Baxter-Sagart):

  • 吏 (lì) 'officer' is [r]əʔ-s;
  • 史 (shǐ) 'scribe' is s-rəʔ;
  • 使 (shǐ) 'to send, to cause' is s-rəʔ;
  • 使 (shì) 'to be sent as an envoy; envoy' is s-rəʔ-s.

I will append also the probably basic etymon, even though it is written with an unrelated character:

  • 理 (lǐ) 'envoy' is m(ə).rəʔ (or probably just rəʔ for this word).

The relation between all the words is clear:

  1. we have a basic root rəʔ 'to serve' (which, per Schuessler, is the same as 理 'to regulate, to administer'; Baxter-Sagart p. 144),

  2. from which we get 吏 'officer' rəʔ-s with the ordinary nominalizing suffix -s,

  3. with the valency-increasing prefix s- we move to 使 'to send, to cause' s-rəʔ,

  4. and finally nominalize the latter as 使 'envoy' s-rəʔ-s ('one who is sent').

(The verbal meaning for 使 'to be sent as an envoy' s-rəʔ-s seems to be a later development when the Old Chinese morphology alrealy broke up at it became possible to just fluidly change parts of speech, per Schuessler p. 350; same for 史 'scribe' s-rəʔ, which looks like a direct change of parts of speech from 使 'to send, to cause, to employ' s-rəʔ).

From these on, the current pronunciations are all directly derivable. Thus, 吏 actually maintains the original consonant the best of all; all the rest in the group use the valency-inclreasing s- prefix and thus obtain the initial s-r- cluster, which is quite expectedly simplified to a retroflex version of [s], that is, [ʂ].

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I'm entirely unqualified to talk about phonology, but from I can tell, 吏, 史 and 事 all evolved from the same character, thus probably share the similar pronounciation in ancient times. 吏's entirely different pronounciation is likely a result of 训读, where the pronouciation and the glyph of a character mismatch. Nowadays 训读 usually refers to this phenonmenon in Japanese, but it did happen in Chinese as well. Also see 文白异读Literary and colloquial readings

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    a related explanation: The characters 史 (history), 吏 (government official), 使 (cause; use; instruct), and 事 (matter; work; affair) are all etymologically related and all derive from the same ancient character, depicting a hand (又) holding a container for writing utensils. 事 and 史 were originally written the same, but later an extra mark was added to distinguish them. (dong-chinese.com/wiki/%E4%BA%8B) Oct 5, 2022 at 4:31
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Words that look similar do not always share the same origin or phonic element.

e.g.

人 and 入; 全 and 金; 赤 and 亦

木,林, and 森 all sound different from each other

Sometimes, two different parts from two different characters would evolve into the same form

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