Exam_1-_Winter_2008_blank_copy - W08 Exam 1 Blank Copy I(22...

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

View Full Document Right Arrow Icon
W08_ Exam 1 Blank Copy 1 A) ( JACS , 2006 , 128, 8128) Geosim is the volatile compound responsible for the characteristic smell of freshly turned soil. Identify the following information about geosim. I. (22 points) OH CH 3 CH 3 i) How many 13 C NMR signals? ii) How many stereoisomers does geosim have? iii) Geosim will reaction with Cr +6 to produce a color change. ( circle one ) True or False iv) Write the IUPAC name for geosim: geosim B) ( JOC, 2008 , 73, 2) O O OH OH Excess CH 3 OCH 2 Cl ((CH 3 ) 2 CH) 2 NCH 2 CH 3 (base) C) ( JOC, 2007 , 72, 9991) O H O O C H CH 3 Li 1) 2) H 3 O + (protonation) How many stereoisomers of B are possible? Compound B (no stereocheistry needs to be shown) D) ( JOC, 2007 , 72, 8478) PCC CH 3 O O O E) ( JOC, 2007 , 72, 9046) SCF 2 Br + CH 3 Si CH 3 H 3 C Cl Mg, THF (solvent) + MgBrCl Complete the following reaction sequences, including stereochemistry as required. 2 2 2 4 3 2 1 3 3 H
Image of page 1

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

View Full Document Right Arrow Icon
W08_ Exam 1 Blank Copy 2 A) ( JOC, 2008 , 73, 517) The transformation of Reactant L to Product M takes place as follows: The oxirane oxygen coordinates to the diisobutyl aluminum hydride f ollowed by assisted ionization to open the oxirane, which gives a resonance-stabilized carbocation in the 4-membered ring (see Intermediate J, drawn in the space below). Then, an intramolecular hydride addition takes place where the hydride adds from the less hindered face of the 4-membered ring. Finally, a protonation to remove the aluminum results in Product M.
Image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the 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