HT3-03 - C hemistry 301-301A Hour we know...

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Chemistry 301-301A - Hour Examination #3, December 11, 2003 “..... as we know, there are known unknowns; there are things we know we know. We also know there are known unknowns; that is to say we know there are some things we do not know. But there are also unknown unknowns - the ones we don't know we don't know.” Donald Rumsfeld ( winner of a British award given to the worst mangler of the English language in 2003 ) “I know, a proof is a proof. What kind of a proof is a proof? A proof is a proof and when you have a good proof it's because it's proven." Jean Chrétien (hon. mention for the same award) 1[18 points] (a) Acid-catalyzed addition of water to 3-methyl-1-butene ( 1 ) results in formation of large amounts of a rearranged alcohol ( 2 ), in addition to the expected alcohol ( 3 ). Explain, with excellent arrow formalisms. 1 OH OH + H 2 O H 3 O + 2 3 (b) On the other hand hydroboration of 1 , followed by oxidation, does not lead to any rearranged product. Only alcohol 4 is formed.
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This note was uploaded on 03/07/2010 for the course ORGO 1 AND V.0243 taught by Professor Jones during the Spring '10 term at NYU.

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HT3-03 - C hemistry 301-301A Hour we know...

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