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Why, in American English, is the word Italy is pronounced /ˈɪdəli/ and not /ˈɪtəli/?
What is the rule that is followed in the pronunciation of Italy to make the letter t pronounced like a d? Why is the same rule not followed for Italian, which is pronounced /əˈtæljən/ or /ɪˈtæljən/?

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First two questions: The pronunciation of some American English consonants can be quite different from British English, in particular for R and T. A t in the middle of a word can be pronunced as a soft d in American English (think of bottle, cattle, etc.). See here, for example, for examples of this.

Third question: Why it does happen for Italy and not for Italian is clearly a matter of stress. If the stress is on the t, it usually keeps its pronunciation and is not changed into a soft d. Thus /ˈɪdəli/ but /əˈtæljən/. Another example is (taken from the New Oxford American Dictionary, in US English pronunciation): tautology (/tɔˈtɑlədʒi/) vs tautological (/ˈˌtɔdlˈɑdʒəkəl/), which clearly demonstrate that.

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It may be worth mentioning the glottal stop here which is characteristic of Northern English (my native tongue). The same rules apply as you outlined, but rather than the D sound there is, in fact, no sound! – Dancrumb Feb 24 '11 at 15:11
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@Dancrumb: Ah, but the glottal stop is just as much (or as little) a sound as any other occlusive consonant! – Cerberus Feb 24 '11 at 15:17
@Cerberus: I knew someone would pick me up on whether a glottal stop is a sound or not :o) – Dancrumb Feb 24 '11 at 15:17
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The “soft” t sound of American English is usually described phonetically as a flap or tap and is represented in IPA with the “fishhook r” [ɾ] rather than [d]. – nohat♦ Feb 24 '11 at 19:02
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@nohat: Aye, good work. – Orbling Feb 24 '11 at 19:25
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up vote 7 down vote

Not all Americans do, and not consistently.

Flap-t (/d/ instead of /t/) often happens between vowel sounds or after a vowel and before a liquid.

The t in "-teen" is always pronounced as t. As Henry mentions the reason is that flap rarely happens in stressed positions. As it doesn't happen in Italian.

Here's good explanation of T pronounced D.

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The flap rarely happens at start of a stressed syllable, as in Italian. It is more common in an unstressed syllable, as in Italy. – Henry Feb 24 '11 at 8:43
Absolutely right. – Manoochehr Feb 24 '11 at 8:47
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Consonant softening (voiceless plosives becoming voiced, etc.) is normal in human language, although it is more likely (or, probably, simply faster to occur) between unstressed vowels. Writing -- artificially crystalising pronunciation -- is not the normal state of affairs. That's why pasta e fagioli comes out pastafazool, or capicola is pronounced something like gabbagool, in many Italian dialects. (And yes, I did understand that you meant it doesn't happen in the word Italian -- I'm just using Italian words to demonstrate that it isn't an English phenomenon.) – bye Feb 24 '11 at 18:04
@Stan Rogers: Italian dialects are not dialects of Italian; they are completely different languages. To make an example, in some places of northern Italy they speak a dialect of the Western Lombard or Eastern Lombard; in other places, they speak Ladino. – kiamlaluno Feb 24 '11 at 20:14
@kiamlaluno: The dialects I'm referring to are "merely" dialects of the standard Tuscan. If I had meant differently, I would have said so. (I am aware that Italy as a political entity is defined by geography rather than language.) Any natural "language" is just a collection of dialects (absent a controlling institution), and the phenomena that cause language to change from one to another is constantly at work in all of them. – bye Feb 24 '11 at 22:33
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