Exam 1 1-26-11 KEY

Exam 1 1-26-11 KEY - NAME: KE Y (please PRINT)...

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Unformatted text preview: NAME: KE Y (please PRINT) C/zemzérz‘rylogfi’ Examl January 26, 2011 0 Value Total Score . 36 . —'—_ T "— 4.| 4+5+4 ' 13 I l 5. l 1 x 15 ‘ 15 l I l 6. l 1 x 14 l 14 | | I 100 l Decadane Malkanes, )1. Chemical term for an unpleasant family of nuladjusted alkanes‘ 1. Provide the major organic product(s) from the following transformations (in the boxes provided). Be sure to include stereochemical information where appropriate. [36 points] 1. n—BuLi, THF m \) 2. Do V am 3. CrO3-2pyr, CHZCIZ (a) % (b) N Brz' A (c) 7? I‘LOH (d) l /><8:)4 _ D 1. NBS, 0014, hv ———-———-———> 2. Mg°, THF 3. D20 1. PBrs —————————) 2. NaCN, DMF, A 2. Will the following reaction proceed as shown below? If not, explain briefly. [10 points] 1. 2Li°, EtZO —-—) Cl 2. Do, EtOH OH fi 0 0' ‘ /’{ul h 4.1 I! I M AA . (“1‘ NM ?/ l/ '1 ./iv ,r' 3. Give the approximate pKa's for protons (D through [12 points] 20 _11_ 2K 14.0 «r ®@®® 4. Provide answers to each of the following: [13 points] (a) Give the structure for the following compound: ciS—3—methylcyclopentanecarbaldehyde (1). (b) Give the product formed when 1 is treated with Jones reagent. 13-600" (0) Give the IUPAC name for the following nonracemic compound: W 35’ g5 . 3-05m « g— muhyl — 2’ Manor): Cl 0 , ‘ 5. Acetylene is initially treated under oxymercuration conditions, to which is then added (in step 2) NazCr207. What water—soluble organic product would be formed? Draw the sequence, including starting material, reagents, intermediate(s), and final product. [15 points] *1 Mama: //’” (Macao —»—-—-a 5mm (tons) Halo "l a“ H 1‘32!!!“ and. H! H a 3 9’ L—a «:9 '=4 flak" ’4' \f” u u n 6. The sequence for a hydroboration/oxidation of a terminal alkyne calls for an initial treatment of the substrate with BH3 (e.g., in THF; step 1), then once hydroboration is complete, introduction of basic peroxide (step 2), as shown below. Explain why aqueous HOOH/HO' cannot be added concurrently with borane. [14 points] 1. borane R—-—:_—__—H ————> product 2. H202, Ho- . ) Nix ' K MWLWMML ...
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This note was uploaded on 02/01/2011 for the course CHEM 109B taught by Professor Aue during the Winter '08 term at UCSB.

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Exam 1 1-26-11 KEY - NAME: KE Y (please PRINT)...

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