Practice_Exam_3 - b N H(H 3 C 2 N 1 MeI(excess 2 Ag 2 O/H 2...

Info icon This preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Page 1 PRACTICE EXAM Spring 2008 Exam 3 – CH 0320 NAME ___________________________________ Good luck!
Image of page 1

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

View Full Document Right Arrow Icon
Page 2 1. Give an example for each description. Use Fisher, Haworth, or conformational representations. a) An aldopentose: b) A ketohexose: c) Methyl β -D-ribopyranoside: d) L-xylose: e) Xylitol: f) Any reducing sugar:
Image of page 2
Page 3 2. Provide products for each of the following transformations. H O CHO OH H OH H H HO OH H CH 2 OH H O O H CHO H HO H HO H OH OH H CH 2 OH CHO H HO H HO CH 2 OH CHO H HO H HO CH 2 OH HNO 3 /H 2 O CH 3 NH 2 /H + HS SH BF 3 NHNH 2 HCN Br 2 /H 2 O a b c d e f Mannich 2 equivalents C 7 H 13 NO
Image of page 3

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

View Full Document Right Arrow Icon
Page 4 3. For each of the following transformations, provide mechanisms. (8 points each) a) Show each bond forming step, including deprotonations and protonations. b) Show correct formal charges on each atom that is not neutral. c) In base catalyzed reactions, show an appropriate source for protonation. (for example, H 2 O or HOR). a. O HO HO OH O H 3 CO HO OH HOCH 3 /H +
Image of page 4
Page 5 3 (continued – Show the mechanism).
Image of page 5

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

View Full Document Right Arrow Icon
Image of page 6
Image of page 7

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

View Full Document Right Arrow Icon
Image of page 8
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: b. N H (H 3 C) 2 N 1) MeI (excess) 2) Ag 2 O/H 2 O/heat Page 6 4. Show you would prepare glucose from a pentose using the Kiliani-Fisher method. Show all reagents. Choose the appropriate starting material. Show all intermediates, but it is not necessary to show mechanism. Page 7 5. Devise a preparation of the following amine using the reductive amination conditions. N H CH 3 Page 8 6. a) Draw a hexose that will give an optically active product after treatment with nitric acid. b) Draw a pentose that will afford an optically inactive alditol. 7. Ruff degradation of Aldose A affords a pentose. The same pentose is formed through a Kiliani-Fisher synthesis beginning with D-threose. Treatment of Aldose A with NaBH4 affords an achiral product. What is Aldose A? Show your reasoning....
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