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What is the underlying argument between the two pronunciations and what are the multiple ways to deal with the problem?

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You mean in "Ashre"? – msh210 Mar 20 '11 at 5:02
up vote 5 down vote accepted

Per the Mishna Berura "Know that some say that the word זכר should be pronounced as "Zaicher" with a "Tzairai" and some say that it should be pronounced "Zecher" with a "Segol." Therefore, it is correct to read it twice.

The Mishnah Berurah does not cite a source for the two opinions, however some have suggested that the source is the following letter by Rabbi Chaim Volozhin. Rabbi Chaim was a leading student the Gaon of Vilna, and the following is a section of a letter that was written by Rabbi Chaim to the publisher of Ma'aseh Rav, a collection of testimonies about the Vilna Gaon's personal customs.

"As for what you wrote to say in Parshas Zachor, Zecher, I heard from the holy mouth of the Vilna Gaon that he read it Zaicher. I do not know whether those who claim to have heard otherwise are mistaken or whether he changed his mind in his old age. Please try to find out the truth."

The different ways I have seen are either totally repeating the Posuk and saying the word differently or just repeating from Timche with the other pronunciation.

See Igros Moshe for further discussion. http://hebrewbooks.org/pdfpager.aspx?req=922&st=&pgnum=111

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As far as practice goes, I've heard from many people that the Lubavitcher Rebbe would say "zeicher zecher rav". – HodofHod Dec 21 '11 at 6:47
@HodofHod: judaism.stackexchange.com/questions/6142 – msh210 Feb 12 '12 at 16:00
But you forgot to mention what Reb Chaim of Volozhin - THE Talmid of the Vilna Gaon wrote in his haskomo to that Sefer - Ma'aseh Rav: "ואשר כתב לקרות בפ' זכור זכר בשש נקודות אני שמעתי מפה קדוש שקרא בחמש נקודות ולא ידעתי אם השומעים שמעו וטעו לומר בשש נקודות או אולי בזקנותו חזר בו". Source: herzog.ac.il/tvunot/fulltext/mega10_broyer.pdf – Danny Schoemann Sep 3 '14 at 13:36

A comprehensive article about this was written by the late Rav Mordechai Breuer, published in Megadim 10, Shvat 5750.

(link: http://www.herzog.ac.il/tvunot/fulltext/mega10_broyer.pdf)

He discusses the "Zeicher" issue, as well as "V'laharog" and "Lifneihem" in the Megillah (discussed in Rav Moshe's teshuvah).

He traces the history of the variant pronunciation back to the Radak, and discusses the mesorah for the word from sources like the Keter and the Minchat Shai.

His conclusion is that from a masoretic perspective, "Zeicher" with a tzeireh is correct--but it's really worth reading the whole article.

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