ORGO test - 1 (18 points). Compound 1 can be converted into...

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1 (18 points). Compound 1 can be converted into an alcohol or alcohols under three sets of conditions. Your jobs are to: First use the partial spectral data (solvent CDCl 3 ) to provide structures for A , B , and C . Briefly explain how you used the data. Next, supply appropriate reagents over the arrows. Be careful to indicate separate synthetic steps with 1, 2, etc. Mechanisms are not necessary. 1 1 A partial 1 H NMR spectra ! 3.53 (triplet) ! 3.78 (doublet of quartets) B 1 B and C no signal for C between ! 3.5 " 4.0
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2 (16 points). Racemic compound 2 gives four structurally different alcohols when treated with H 3 O + /H 2 O. Only one of them, X , gives 3 when treated with NaH. Give us the four alcohols, show us which one is X and goes on to 3 , and explain with a mechanism why it is only alcohol X that gives 3 . Cl 2 H 3 O + /H 2 O NaH 3 O X Over for explanation and mechanism.
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3 (20 points). Supply appropriate reagents for the following conversions. You must use the indicated starting material, but you may also use anything inorganic (no carbons) and
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This note was uploaded on 01/27/2012 for the course CHEM CHEM-UA taught by Professor Jones during the Fall '11 term at NYU.

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ORGO test - 1 (18 points). Compound 1 can be converted into...

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