Exam 1 1-26-11 - NAME(please plan szemértryiogfi ExamI 0...

Info icon This preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: NAME: (please plan) szemértryiogfi ExamI January 26, 2011 0 Value Total Score 36 . T w l 4 x 3 —_12— h 4.‘ 4+5+4 ’ 13 ‘ l 5. | 1x 15 | 15 \ l | 6. I 1x 14 | 14 ‘ I l 100 | Malkanes, 1:. Chemical term for an unpleasant family of maladjusted 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 00 [>0 \ 3. 2Cr03~2pyr, CHZCIZ Br2. A (b) s» ——————> H 1. NBS, CCI4, hv ——-—) (c) 2. ma THF 3. D20 H OH ‘2. 1. PER; (d) ————> 2. NaCN, DMF, A 2. Will the following reaction proceed as shown below? If not, explain briefly. [10 points] 1. 2Li°, Et20 0' 2. Do EtOH 3. Give the approximate pKa's for protons ® through @. [12 points] (969699 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. (0) Give the IUPAC name for the following nonracemic compound: 5. Acetylene is initially treated under oxymercuration conditions, to which is then added (in step 2) Na2Cr207. What water-soluble organic product would be formed? Draw the sequence, including starting material, reagents, intermediate(s), and final product. [15 points] 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 2 H —> product 2. H202, Ho- ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern