Fun With Words

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English is a language which permits the legitimate extension of existing words to serve new purposes by the addition of prefixes and suffixes.

This is sometimes referred to as agglutinative construction.

This process can create arbitrarily long words: for example, the prefixes pseudo (false, spurious) and anti (against, opposed to) can be added as many times as desired.

A word like anti-aircraft (pertaining to the defense against aircraft) is easily extended to anti-anti-aircraft (pertaining to counteracting the defense against aircraft, a legitimate concept) and can from there be prefixed with an endless stream of "anti-"s, each time creating a new level of counteraction. More familiarly, the addition of numerous "great"s to a relative, e.g. great-great-great-grandfather, can produce words of arbitrary length.

"Antidisestablishmentarianism" is the longest common example of a word formed by agglutinative construction, as follows (the numbers succeeding the word refer to the number of letters in the word):

establish (9)
to set up, put in place, or institute (originally from the Latin stare, to stand)

dis-establish (12)
to end the established status of a body, in particular a church, given such status by law, such as the Church of England

disestablish-ment (16)
the separation of church and state (specifically in this context it is the political movement of the 1860s in Britain)

anti-disestablishment (20)
opposition to disestablishment

antidisestablishment-ary (23)
of or pertaining to opposition to disestablishment

antidisestablishmentari-an (25)
an opponent of disestablishment

antidisestablishmentarian-ism (28)
the movement or ideology that opposes disestablishment

The use of additional affixes could stretch the word to the oft-cited 'pseudoantidisestablishmentarianism' (34) or 'antidisestablishmentarianisticalized,' (36)

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Common words in general text
Most of the longest English words are not likely to occur in general text, meaning non-technical present-day text seen by casual readers, in which the author did not specifically intend to use an unusually long word.

The longest words likely to be encountered in general text are deinstitutionalization and counterrevolutionaries, with 22 letters each.

A computer study of over a million samples of normal English prose found that the longest word one is likely to encounter on an everyday basis is uncharacteristically, at 20 letters.

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Typed words
The longest words typable with only the left hand using conventional hand placement on a QWERTY keyboard are tesseradecades, aftercataracts, and the more common but sometimes hyphenated sweaterdresses.

Using the right hand alone, the longest word that can be typed is johnny-jump-up, or, excluding hyphens, monimolimnion.

The longest English word typable using only the top row of letters has 11 letters: rupturewort.

Similar words with 10 letters include: pepperwort, perpetuity, proprietor, typewriter, requietory, repertoire, tripertite and pourriture. The word teetertotter (used in North American English) is longer at 12 letters, although it is usually spelled with a hyphen.

The longest words typable by alternating left and right hands are antiskepticism and leucocytozoans respectively.

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Words with certain characteristics of notable length

Strengths is the longest word in the English language containing only one vowel.

Rhythms is the longest word in the English language containing none of the five recognised vowels.

Schmaltzed and strengthed appear to be the longest monosyllabic words; but if squirrelled is pronounced as one syllable only, it is the longest.

The longest words with no repeated letters are dermatoglyphics, misconjugatedly and uncopyrightables.

The longest word whose letters are in alphabetical order is the eight-letter Aegilops, a grass genus.

The longest words recorded with each vowel only once, and in order, are abstemiously, affectiously, and tragediously.

Facetiously is among the few other words with single occurrences of all five vowels and the semivowel y.