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Patrick Henry and Francis Scott Key are out, but Susan B. Anthony and Nancy Pelosi are in. The White House was cut, but New York and Sept. 11 made the list.

Federal immigration authorities on Thursday unveiled 100 new questions that immigrants will have to study in order to pass a civics test to become naturalized American citizens. The redesign of the test, the first since it was created in 1986 as a standardized examination, follows years of criticism in which conservative groups said the test was too easy and immigrant advocates said it was too hard.

The new questions did little to quell that debate among many immigrant groups, who complained the citizenship test would become even more daunting. Conservatives seemed to be more satisfied.

Bush administration officials said the new test was part of their effort to move forward on the hotly disputed issue of immigration by focusing on the assimilation of legal immigrants who have played by the rules, leaving aside the situation of some 12 million illegal immigrants here.

Several historians said the new questions successfully incorporated more ideas about the workings of American democracy and better touched upon the diversity of the groups — including women, American Indians and African Americans — who have influenced the country’s history.

Would-be citizens no longer have to know who said, “Give me liberty or give me death,” or who wrote “The Star-Spangled Banner.” But they do have to know, “What did Susan B. Anthony do?” and who the current speaker of the House of Representatives is.

Alfonso Aguilar, a senior official at Citizenship and Immigration Services, the agency that designs and administers the test, said it was not intended to be punitive.

“We don’t seek to fail anyone,” said Aguilar, an architect of the test.

Immigration officials said they sought to move away from civics trivia to emphasize basic concepts about the structure of government and American history and geography. In contrast to the old test, which some immigrants could pass without any study, the officials said the new one is intended to force even highly educated applicants to do some reviewing.

“This test genuinely talks about what makes an American citizen,” said Emilio Gonzalez, the director of Citizenship and Immigration Services, speaking at a news conference in Washington.

The $6.5-million redesign was crafted over six years of discussions with historians, immigrant organizations and liberal and conservative research groups. The questions were submitted to four months of pilot testing earlier this year with more than 6,000 immigrants who were applying for naturalization.

The agency will begin to use the revised test on Oct. 1, 2008, to leave a year for aspiring citizens to prepare and for community groups to adjust their study classes.