Midterm I - Name ‘ page 2 I Shown below is the folate...

Info icon This preview shows pages 1–4. 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

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

View Full Document Right Arrow Icon
Image of page 4
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Name: ‘ page 2 . I. Shown below is the folate analog methotrexate. Circle five different functional groups on the molecule. Name the functional groups and indicate their pKas (in intervals of 5, Le. 5, 10, 15, etc.) (10 minutes, 20 points total) :5) aromatic ring 1—3 5 tr?) we‘ll) we 3mm \0 (“3 gm». {:‘1% 35- %) promo’ffid 893- N 5 Name: page 3 II. For each of the substitution or elimination reactions shown below, (I) fill in the box with the appropriate reagent, major product or starting material. If NO REACTION occurs, wn'te “NR”. (2) Indicate if each reaction is SNl, 8N2, E], or E2. Remember to clearly indicate the re gi ochemistry and stereochemistry for each reaction. Choose 3 of the 4 problems. (20 minutes, 40 points total) 1. ‘6 G) 1. M60 Na , MeOH 0% —*—~ 2. M 2. G) ($an \Q 0 ‘0 e _ NH2 0K resonantfi SMMfiS Os Same . molQCUL-LL 3. tBIig) if? Me: tBuOH El — Pr E2— 4. NHgMe DMF Name: I page 4 1]]. Draw a detailed, arrow-pushing mechanism for the following reaction. (10 minutes, 20 points) 9N? OMe + Mel —*—‘—* + Na] DMF 0: Name: page 5 IV. Cystine can be reduced to cysteine using tributylphosphine in aqueous THF. Propose a reasonable mechanism for the reduction, shown below. (10 minutes, 20 points) P LEI-12 w BU3P SH H02C\_./\S’S\/\C02H —>- 2 + BU3P=O m V\ HZOEHF HzN C02H Ev??? "’3 RH; “01%" ® - a“ ; $3.“???‘L5 '* S\AC02_H H"; H . _ H H0 :31 a $ - ~ b3?“ 2‘ 2— %SM?L‘¢ 3) A” HSVKCO {(1% * 1}} 2H ‘3" <22» .‘c‘::3—~H HO Q “ <3 (~59 ”—‘P MD <1 . 2. W - + M 2 spew é?“ gs? SEMS if”, N .. _. F4 41 fit K] K} § KO“ 1\ p“ ELK-5 ...
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