TRANSMITTANCE 135 Compound A has 4 carbons and one heteroatom (not C or H). a. Please give appropriate structure for compound A. b. Please give the reaction scheme of compound A mixed with NaOH. c. Please give the mechanism and label the direction of the equilibrium for this reaction. Compound A D 4000 3000 2000 1500 1000 500 HAVENUMBERI-

TRANSMITTANCE 135 Compound A has 4 carbons and one heteroatom (not C or H). a. Please give appropriate structure for compound A. b. Please give the reaction scheme of compound A mixed with NaOH. c. Please give the mechanism and label the direction of the equilibrium for this reaction. Compound A D 4000 3000 2000 1500 1000 500 HAVENUMBERI-

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations

Section11.SE: Something Extra

Problem 40AP: The following Walden cycle has been carried out. Explain the results, and indicate where Walden...

See similar textbooks

Similar questions

k. N,N-diisopropylethylamine 100 80 60 40 20- 25 50 75 100 125 m/z Identify the structure that give rise to the peak at m/z 72 and 114. I. Butyramide (C4H9NO) 100- 'NH2 80 60 40 20 10 20 30 40 50 60 70 80 90 m/z Identify the structure and provide the mechanism that give rise to the peak at m/z 59. Relative Intensity Relative Intensity
7. Propose a structure for the alkene having the mass spectrum shown below. Assume that there are no double bond rearrangements occurring. M+ is at 84, major fragments at 69, 43, 41. Identify the major fragmentations/fragments using a proposed structure.. MASS SPECTRUM 100 80 60 40 20 0.0+ 0.0 20 40 60 80 100 m/z Rel. Intensity
uestion 8 of 8 Step 2 Draw step 2 of the mechanism. OりCX 0 @ H + H,C CI Br .. MacBook Air 吕口 888 F5 F7 FB F10 23 2$ 4 & 2 3 5 7 8 9 W E R. T Y D F K T Z +| +† +t +l *3
12. Consider the data below to answer the following questions. C₂H₁40 IR: MS: 1715 cm-¹ M* at m/z = 114, a-cleavage fragment at m/z=71 McLafferty rearrangement fragment at m/z = 86 ¹H NMR: 0.928 (6H, triplet) 1.59 8 (4H, sextet) 2.36 8 (4H, triplet) a) Calculate the degree of unsaturation for this compound. b) What functional group is indicated by the IR data? c) Propose a structure consistent with the spectral data presented above. d) Interpret the mass spectral data by showing both fragmentation patterns.
(20 pts) Alcohol A undergoes a remarkable acid-catalyzed conversion to B. Me Me Me HO Me I Me S Me Me + HA H H (cat.) Me Me Me Me A Hmm Hmm Me Me 11111 Me B Me Me a. Provide a mechanism. It may take a while to draw out all the intermediates, but consider this as a step- by-step process, although one could also imagine mechanistic alternatives where all or some of the steps are concerted. (attach additional page with your mechanism) b. What do you notice about the stereochemistry of each 1,2-shift in your mechanism (or at least where the stereochemistry of the shift is apparent from the structure of B)? c. How many 1,2-shifts are there in total? d. Give a one-word name to the final step in your mechanism.
Spectrum No.1 The infrared spectrum has no interesting features except aliphatic C-H stretching and bending. Give the mechanism that lead to the formation of ion fragments at m/2 = 83 & 55. Relative Intensity 100- Relative Intensity 80 60 9 20- 0-tm 10 100- 80 09 MS-NA-3722 9 20 20 MS-NU-3100 0-t 10 30 20 41 40 Spectrum No.2 The infrared spectrum has a medium intensity peak at about 1650 cm³¹. There is also a C-H out-of- plane bending peak near 800 cm³. Give the mechanism that lead to the formation of ion fragments at m/z = 69. 30 50 55 41 40 60 m/z 70 50 m/z 56 83 60 90 69 M(98) 70 100 110 M(84) 80
Decide what H and C atoms in your final product should fit the reported chemical shifts and answer any additional questions. The literature data are for the free base fluoxetine product not the oxalate product. HNMR (60 MHz, CDCI3) d 1.9-2.2 (10H, m), 5.2 (1H, t), 6.8-7.4 (9H, m). 13C NMR (91 MHz, CDCI3 ) d 160.5, 141.0, 128.6, 127.6, 126.5, 125.7, 122.8, 124.3 (q. J = 267 Hz), 122.5 (q, J = 30 Hz), 115.7, 78.5, 55.7, 45.5, 36.8. %3D 1. For the 13C spectrum: notice the signals at 124.3 and 122.5 are split into quartets. This is unusual for the 1°C NMR of many organic compounds. Why is this observed in the spectrum for fluoxetine.
Be sure to AUSTET All parts. Select the meckanistic steps thRE Tould produce "major prodoct Y" via a 12-bydride shift daring a dehydration of "alcobol X". major product Part 1: Seep 1: Part 2: Sep 2: OH 121 HSO, * HSO *HS0, Part 3: Step 3: Part 4 out of 4 Step 4: 14 HSO, HSO, 141 141 HSO FOSH Naxt part
R; = 0.70 R = 0.55 R; = 0.47 -+------ Eluent: EtOAc OH ОН OH 1 2 3 5. Which compound corresponds to Rf = 0.70? O Standards are needed for reference. 1 3
DEPT-135 DEPT - 90 DEPT - 45 T 200 CDS-03-521 180 4/5 160 140 - H₂CO T 120 75% + 100 ppm U 80 LL 60 40 20 0
The leaves of the Brazilian Tree Senna multijunga contain a number of pryidine alkaloids that inhibit acetylcholinterinase. Two recentyl isolated isomeric compounds have the strcture have the strcture shown below. (NOTE: M=293) Use the mass spectral data provided to determine the precise location of the hydroxyl group in each isomer. Isomer A: EI-MS, m/z(rel. int): 222(20), 150(10), 136(25), 123(100) Isomer B:EI-MS, m/z(re;. int): 236(20), 150(10), 136(25), 123(100)
Wittig Reaction *PPH3 PPH3 NANH2 H, + NH3 + NaBr H. + Br PPH3 H. H. THE + PH3PO Assign the characteristic signals on the following IR spectrum. 100 BIO-RAD 95 - 90 85 80 trans-Stilbene 75 70 65 60 4000 3500 3000 2500 2000 1500 1000 500 Wavenumbers Why did we need to exclude water from the reaction? What would happen if too much water was present? Why do we need to do a recrystallization after running the column chromatography? % Transmittance 3082.4 1490.7