Midterm I - flflSNMfl 1. Shown below is the folate...

Info iconThis preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

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

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

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

View Full DocumentRight Arrow Icon
Background image of page 4
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: flflSNMfl 1. Shown below is the folate analog methotrcxate. Circle five different functional groups on the molecule. Name the functional groups and indicate their pKas (in intervals of 5, i.e. 5, 10, 15, etc.) (10 minutes, 20 points total) i\ Car bolélc acid I ‘3. 2) amehfi. 56 'alol‘C-Ebefl ?:® amine lb atom-om flog H 5 or'om'nalefi\ amine \0 amtfl-fl b {Mama’de 1 Name: page 3 II. For each of the substitution or elimination reactions shown below, (1) fill in the box with the appropriate reagent, major product or starting material. If N0 REACTION occurs, write “NR”. (2) Indicate if each reaction is SN], 8N2, E1, or E2. Remember to clearly indicate the regiochemistry and stereochemistry for each reaction. Choose 3 of the 4 problems. (20 minutes, 40 points total) 1. e 69. MeO Na , MeOH SH —-—~—————-—+ U 2- M 2. GE) NH»; O Nl-Ig r2” Q E“ , e 0K Wgonencfi chturfis 0A? Selma rflOLQOpLLQ. 3. tB118)l\€lj-> Me He tBuOII Er ‘ ‘Pr 4. N}12Me DMF Name: page 4 II]. Draw a detailed, arrow-pushing mechanism for the following reaction. (10 minutes, 20 points) 0qug9 OMB + Mel W + N81 DMF N a?) CF“ #4 h. # h-fi—L 370/ +Na1 Name: m_—_ 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) .. NH Q5 3 2 w Bu3P: SH { _ H02C\/‘\ /S\/\1 —)... 2 S\ + BU3PZO ; S COZH 1120:3111: fiHz Lia HgN (3021i EUCJ? - "y; - NH; Hm; , es, £3, 5 2 NW»... 4, \P. V - 57 g Q “Li ( ‘$\\AC0;H NHL \‘w‘ n I; u) Hi) s . ~ *3? \ ’35s": ‘” “ U "73 02H War-3.? «SJ JED—H m ~ o 6:: ms \ . ¥\¢,¢’M {5; : Jr i “‘12 \.,.v__r(d_,\h g .r n _: 1 ‘ . {£1 a « ' M ...
View Full Document

This test prep was uploaded on 04/07/2008 for the course CHEM C3443 taught by Professor Cornish during the Spring '08 term at Columbia.

Page1 / 4

Midterm I - flflSNMfl 1. Shown below is the folate...

This preview shows document pages 1 - 4. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online