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unless (conj.)

mid-15c., earlier onlesse,
from (not) on lesse (than) "(not) on a less compelling condition (than);" see less.
The first syllable originally on, but the negative connotation and the lack of stress changed it to un-. "Except could once be used as a synonym for unless, but the words have now drawn entirely apart" [Century Dictionary].

I ask about only one determinant of change: the negative connotation. 1. How'd it cause 'on' to change, when the negative connotation is wholly spwaned by 'less'?

  1. To a Middle English layperson, wouldn't prefixing 'less' with 'un' reverse the meaning of 'unless'? As 'less than good = not good', wouldn't

un + less than good
= not + not good
= good?

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    ON is just the way they used to spell what we spell UN. Spelynge hath y-changed. – John Lawler Apr 9 '18 at 0:37
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    @JohnLawler If so, then would Etymonline be wrong to impute 'the negative connotation' to this prefix change? – Greek - Area 51 Proposal Apr 9 '18 at 19:42
  • I have no idea what they mean by "the negative connotation". The prefix is negative, that's all. No connotation involved. – John Lawler Apr 10 '18 at 2:57
  • @JohnLawler The prefix used to be the preposition on, which is not negative. At some point, the general negative connotations of the phrase/word caused the prefix to shift from the preposition on to the negating prefix un-. Spelling is not the essential part here; un- has been written that way since Old English, generally distinct from on-. – Janus Bahs Jacquet Oct 26 '18 at 11:18
  • In some dialects. In others, other things happened. Similar remarks famously apply to black and blank, which meant 'black' and 'white', but not necessarily in that order, all through Middle English times -- dialects and idiolects varied a great deal in which meant which. – John Lawler Oct 26 '18 at 17:44
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This is almost a form of rebracketing-- in which a word's roots are re-defined by misunderstanding, like alcoholic (which has roots in al-kohl and the suffix -ic, but was rebracketed as alco-holic, allowing for the suffix -holic to appear in words like workaholic or coffeeholic)-- crossed with a mondegreen-- a mishearing leading to respelling, like eggcorn for acorn, or like in the game Telephone. As the prefix on- became relatively obsolete and the phonetically-similar prefix un- gained popularity, the on- in onless got redefined as un-, incorrectly. This is an example of a false etymology.

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