Nickel-Catalyzed Reductive Conjugate Addition to Enones Via Allylnickel Intermediates. Supporting Information NMR Spectra

Size: px
Start display at page:

Download "Nickel-Catalyzed Reductive Conjugate Addition to Enones Via Allylnickel Intermediates. Supporting Information NMR Spectra"

Transcription

1 S51 Nickel-Catalyzed Reductive Conjugate Addition to Enones Via Allylnickel Intermediates Ruja Shrestha, Stephanie C. M. Dorn and Daniel J. Weix*. *Department of Chemistry, University of Rochester, Rochester, NY Present Address: Department of Chemistry, University of California, Berkeley, CA Supporting Information NMR Spectra VIII. NMR Spectra (separate pdf file) Compound 1 1 H NMR Compound 1 13 C NMR Compound 1 IR spectrum Compound 2 1 H NMR Compound 2 13 C NMR Compound 3 1 H NMR Compound 3 13 C NMR Compound 4 1 H NMR Compound 4 13 C NMR Compound 5 1 H NMR Compound 5 13 C NMR Compound 6 1 H NMR Compound 6 13 C NMR Compound 7 1 H NMR Compound 7 13 C NMR Compound 8 1 H NMR Compound 8 13 C NMR Compound 9 1 H NMR Compound 9 13 C NMR Compound 10 1 H NMR Compound C NMR Compound 11 1 H NMR Compound C NMR Compound 12 1 H NMR Compound C NMR Compound 13 1 H NMR Compound C NMR Compound F NMR Compound 14 1 H NMR Compound C NMR Compound 15 1 H NMR Compound C NMR Compound 16 1 H NMR Compound C NMR Compound 17 1 H NMR Compound C NMR Compound 18 1 H NMR Compound C NMR Compound 18 IR spectrum Compound 19 1 H NMR Compound C NMR Compound 20 1 H NMR Compound C NMR Compound 21 1 H NMR S53 S54 S55 S56 S57 S58 S59 S60 S61 S62 S63 S64 S65 S66 S67 S68 S69 S70 S71 S72 S73 S74 S75 S76 S77 S78 S79 S80 S81 S82 S83 S84 S85 S86 S87 S88 S89 S90 S91 S92 S93 S94 S95 S96

2 S52 Compound C NMR S97 Compound 22 1 H NMR S98 Compound C NMR S99 Compound 23 1 H NMR S100 Compound C NMR S101 Compound F NMR S102 Compound 24 1 H NMR S103 Compound C NMR S104 Compound 25 1 H NMR S105 Compound C NMR S106 Compound F NMR S107 Compound 26 1 H NMR S108 Compound C NMR S109 Compound F NMR S110 Compound 27 1 H NMR S111 Compound C NMR S112 Compound F NMR S113 Compound 28 1 H NMR S114 Compound C NMR S115 Compound 29 1 H NMR S116 Compound C NMR S117 Compound 30 1 H NMR S118 Compound C NMR S119 Compound 31 1 H NMR S120 Compound C NMR S121 Compound F NMR S122 Compound 32 1 H NMR S123 Compound C NMR S124 Compound 33 1 H NMR S125 Compound C NMR S126 Compound 34 1 H NMR S127 Compound C NMR S128

3 ppm Scheme 1 1 S53

4 S Scheme ppm

5 S55

6 ppm Me Scheme 1 2 S56

7 S Scheme 1 Me ppm

8 ppm Scheme 1 3 S58

9 S Scheme ppm

10 ppm O OMe 4 Scheme 1 S60

11 S OMe O 4 Scheme ppm

12 ppm O O 5 Scheme 1 S62

13 S O O 5 Scheme ppm

14 ppm O O 1 : 1 ratio of diastereomers 6 Scheme 1 S64

15 S O O 6 Scheme 1 1 : 1 ratio of diastereomers ppm

16 ppm O O 6 : 1 ratio of diastereomers Scheme 1 7 S66

17 S O O 7 Scheme 1 6 : 1 ratio of diastereomers peaks picked for major diastereomer only peaks for minor diastereomer could not be resolved ppm

18 ppm Scheme 1 8 OSi n Pr 3 Me S68

19 S OSi n Pr 3 8 Scheme 1 Me ppm

20 ppm OSiMe 2 t Bu Me 9 Scheme 1 S70

21 S OSiMe 2 t Bu 9 Scheme 1 Me ppm

22 ppm Me Scheme 2 10 S72

23 S Me 10 Scheme ppm

24 ppm OMe Scheme 2 11 S74

25 S OMe 11 Scheme ppm

26 ppm NMe 2 Scheme 2 12 S76

27 S Scheme 2 NMe ppm

28 ppm ppm F Scheme 2 13 S78

29 S Scheme 2 F ppm

30 S Scheme 2 F ppm

31 ppm O Me Scheme 2 14 S81

32 ppm S Me 14 Scheme 2 O

33 ppm CN Scheme 2 15 S83

34 ppm S Scheme 2 CN

35 ppm OMe 16 Scheme 3 S85

36 ppm S OMe 16 Scheme 3

37 ppm CN Scheme 3 17 S87

38 ppm S CN 17 Scheme 3

39 ppm Scheme 3 S89

40 ppm S Scheme 3

41 S91

42 ppm Cl Scheme 4 19 S92

43 ppm S Scheme 4 Cl

44 ppm Br Scheme 4 20 S94

45 ppm S Scheme 4 Br

46 ppm B O O Scheme B O O 21' major minor S96

47 ppm S O B O 21 Scheme 4

48 ppm SO 2 Me Scheme 4 22 S98

49 ppm S Scheme 4 SO 2 Me

50 ppm SF 5 23 Scheme 4 S100

51 ppm S Scheme 4 SF 5

52 ppm S Scheme 4 SF

53 ppm O H Scheme 4 24 S103

54 ppm S H 24 Scheme 4 O

55 ppm CF 3 Scheme 4 25 S105

56 ppm S Scheme 4 CF 3

57 ppm S Scheme 4 CF 3

58 ppm CF 3 26 Scheme 4 S108

59 ppm S CF 3 26 Scheme 4 hexane

60 ppm S CF 3 26 Scheme 4

61 ppm Me F Scheme 4 27 S111

62 ppm S F 27 Scheme 4 Me

63 ppm S F Me 27 Scheme 4

64 ppm CO 2 Me Scheme CO 2 Me 28' major minor S114

65 ppm S Scheme 4 CO 2 Me

66 ppm OEt O Scheme 4 29 S116

67 ppm S O OEt 29 Scheme 4

68 ppm O Me O Scheme 4 30 S118

69 ppm S O 30 Scheme 4 O Me

70 ppm Scheme 4 31 N H O CF 3 S120

71 ppm S O 31 Scheme 4 N H CF 3 Et 2 O Et 2 O

72 ppm S O 31 Scheme 4 N H CF 3

73 ppm O O Scheme O O 32' major minor S123

74 ppm S O 32 Scheme 4 O

75 ppm Scheme 4 33 S125

76 ppm S Scheme 4

77 ppm Me Scheme 4 34 S127

78 ppm S Me 34 Scheme 4

Name: 1. Ignoring C-H absorptions, what characteristic IR absorption(s) would be expected for the functional group shown below?

Name: 1. Ignoring C-H absorptions, what characteristic IR absorption(s) would be expected for the functional group shown below? Chemistry 262 Winter 2018 Exam 3 Practice The following practice contains 20 questions. Thursday s 90 exam will also contain 20 similar questions, valued at 4 points/question. There will also be 2 unknown

More information

Oxindoles: Formal Total Syntheses of Bis-Cyclotryptamine. Alkaloids, (±)-Chimonanthine and (±)-Folicanthine

Oxindoles: Formal Total Syntheses of Bis-Cyclotryptamine. Alkaloids, (±)-Chimonanthine and (±)-Folicanthine FeCl 3 -Catalyzed Allylation Reactions onto 3-Hydroxy 2- Oxindoles: Formal Total Syntheses of Bis-Cyclotryptamine Alkaloids, (±)-Chimonanthine and (±)-Folicanthine Lakshmana K. Kinthada, Sai Raghavendra

More information

CHEM1102 Worksheet 4 Answers to Critical Thinking Questions Model 1: Infrared (IR) Spectroscopy

CHEM1102 Worksheet 4 Answers to Critical Thinking Questions Model 1: Infrared (IR) Spectroscopy CEM1102 Worksheet 4 Answers to Critical Thinking Questions Model 1: Infrared (IR) Spectroscopy 1. See below. Model 2: UV-Visible Spectroscopy 1. See below. 2. All of the above. 3. Restricted to the identification

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Concise Stereoselective Synthesis of ( )-Podophyllotoxin by Intermolecular Fe III -catalyzed Friedel-Crafts Alkylation Daniel Stadler, Thorsten

More information

Final Exam /415 ( CHEM 6352 Fall %) Name

Final Exam /415 ( CHEM 6352 Fall %) Name Final Exam /415 ( CEM 6352 Fall 2011 %) Name Dec. 15 th, 2011 8:00-12:00 You may NT use any references or aids to complete the following with the exception of a chemical model set and the scrap paper that

More information

Chemistry 333. Final Examination

Chemistry 333. Final Examination Chemistry 333 Final Examination May 15, 2017 Professor Charonnat Be certain that your examination has ten (10) pages including this one. Put your name on each page of this examination booklet. By putting

More information

Name: 1. Ignoring C-H absorptions, what characteristic IR absorption(s) would be expected for the functional group shown below?

Name: 1. Ignoring C-H absorptions, what characteristic IR absorption(s) would be expected for the functional group shown below? Chemistry 262 Winter 2018 Exam 3 Practice The following practice contains 20 questions. Thursday s 90 exam will also contain 20 similar questions, valued at 4 points/question. There will also be 2 unknown

More information

EXAM #3 EXTRA PROBLEMS

EXAM #3 EXTRA PROBLEMS Massachusetts Institute of Technology 5.13, Fall 2006 Dr. Kimberly L. Berkowski rganic chemistry II EXAM #3 EXTRA PRBLEMS What to expect on Exam #3: 1. ~1 Labeling experiment 2. ~2 chanisms 3. ~2 Syntheses

More information

!!!! Organic Chemistry CHM 224. Exam I Questions

!!!! Organic Chemistry CHM 224. Exam I Questions ld Exam I Questions - CHM 224 rganic Chemistry CHM 224 Exam I Questions This set of questions is a compilation of old exams, and does not represent the typical length of an exam - there are more examples,

More information

Chem 2320 Exam 1. January 30, (Please print)

Chem 2320 Exam 1. January 30, (Please print) Chem 2320 Exam 1 January 30, 2006 Name: (first) (last) (Please print) Last 4 digits of I.D. I. Multiple Choice ( /20) Score /60 II /15 III /25 Total score /100 I. Multiple choice questions. (3 points each).

More information

S3 File. Selected NMR spectra, NMR chemical shifts and comparison of 1 H NMR integrals

S3 File. Selected NMR spectra, NMR chemical shifts and comparison of 1 H NMR integrals S3 File. Selected NMR spectra, NMR chemical shifts and comparison of 1 H NMR integrals This file contains: Figure I. 1 H NMR spectrum (D 2 O, 400 MHz) of p-nitrophenyl α-l-fucose. Figure II. 1 H NMR spectrum

More information

Chemistry 233 Exam 3. The Periodic Table

Chemistry 233 Exam 3. The Periodic Table Name: Last First MI Chemistry 233 Exam 3 Fall 2017 Dr. J. sbourn Instructions: The first 8 questions of this exam should be answered on the provided Scantron. You must use a pencil for filling in the Scantron

More information

DBU-mediated Diastereoselective Aldol-type Cyanomethylation of Isatins

DBU-mediated Diastereoselective Aldol-type Cyanomethylation of Isatins DBU-mediated Diastereoselective Aldol-type Cyanomethylation of Isatins V. U. Bhaskara Rao, Krishna Kumar, Tamal Das, Kumar Vanka and Ravi P. Singh * Department of Chemistry, Indian Institute of Technology,

More information

ORGANIC - EGE 5E CH UV AND INFRARED MASS SPECTROMETRY

ORGANIC - EGE 5E CH UV AND INFRARED MASS SPECTROMETRY !! www.clutchprep.com CONCEPT: IR SPECTROSCOPY- FREQUENCIES There are specific absorption frequencies in the functional group region that we should be familiar with EXAMPLE: What are the major IR absorptions

More information

Supporting information. Direct Enantioselective Aldol Reactions catalyzed by a Proline-Thiourea Host- Guest Complex

Supporting information. Direct Enantioselective Aldol Reactions catalyzed by a Proline-Thiourea Host- Guest Complex Supporting information Direct Enantioselective Aldol Reactions catalyzed by a Proline-Thiourea Host- Guest Complex Ömer Reis, Serkan Eymur, Barbaros Reis, Ayhan S. Demir* Department of Chemistry, Middle

More information

Hai-Bin Yang, Xing Fan, Yin Wei,* Min Shi*

Hai-Bin Yang, Xing Fan, Yin Wei,* Min Shi* Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Solvent-controlled Nucleophilic Trifloromethylthiolation of Morita- Baylis-Hillman

More information

CHEM 241 (Davis) Organic Chemistry II Final Exam Friday December 14, NAME (Last, First) DISCUSSION SECTION #

CHEM 241 (Davis) Organic Chemistry II Final Exam Friday December 14, NAME (Last, First) DISCUSSION SECTION # CEM 241 (Davis) rganic Chemistry II Final Exam Friday December 14, 2007 1 NAME (Last, First) DISCUSSIN SECTIN # Initial of last name Instructions Please fill in your name in the space above and on the

More information

Supporting Information

Supporting Information Remarkably Variable Reaction Modes of Frustrated Lewis Pairs with Non-Conjugated Terminal Diacetylenes Chao Chen, Roland Fröhlich, Gerald Kehr, Gerhard Erker Organisch-Chemisches Institut, Westfälische

More information

Chem Final Examination August 7, 2004

Chem Final Examination August 7, 2004 Chem 281 2004-2 Final Examination August 7, 2004 Name: Student Number: Note: You are allowed to use models for this exam. Notes, textbooks and calculators are strictly prohibited. Write your final answers

More information

Chemistry 233 Exam 3 (Green) The Periodic Table

Chemistry 233 Exam 3 (Green) The Periodic Table Name: Last First MI Chemistry Exam (Green) Summer 7 Dr. J. sbourn Instructions: The first questions of this exam should be answered on the provided Scantron. You must use a pencil for filling in the Scantron

More information

Name. Student Number CHM B44Y TEST February 2003 TIME ALLOWED: 100 MINUTES

Name. Student Number CHM B44Y TEST February 2003 TIME ALLOWED: 100 MINUTES Name Student Number M B44Y TEST 3 12 February 2003 TIME ALLWED: 100 MINUTES No models, calculators or other electronic equipment allowed. Tests and exams must be written in non-erasable ink. If you write

More information

Show all work. Remember: a point a minute! This exam is MUCH longer than the upcoming Final.

Show all work. Remember: a point a minute! This exam is MUCH longer than the upcoming Final. CEM 293 Sample Final Dr..M. Muchall Name Show all work. Remember: a point a minute! This exam is MUC longer than the upcoming Final. Textbook and calculator allowed. The textbook can be marked up, but

More information

Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media

Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous

More information

Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex

Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition

More information

Midterm Exam III. CHEM 181: Introduction to Chemical Principles Solutions C HC N H 3 C. pka = 9.7

Midterm Exam III. CHEM 181: Introduction to Chemical Principles Solutions C HC N H 3 C. pka = 9.7 Midterm Exam III EM 181: Introduction to hemical Principles Solutions 1. For reference, here are the pk a values for four weak acids (not all resonance structures shown): N 3 N N 3 3 2 pka = 3.5 pka =

More information

CHEM 203. Final Exam December 15, 2010 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models

CHEM 203. Final Exam December 15, 2010 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models CEM 203 Final Exam December 15, 2010 Your name: ANSWERS This a closed-notes, closed-book exam You may use your set of molecular models This test contains 15 pages Time: 2h 30 min 1. / 16 2. / 15 3. / 24

More information

CHEMISTRY 341. Final Exam Tuesday, December 16, Problem 1 15 pts Problem 9 8 pts. Problem 2 5 pts Problem pts

CHEMISTRY 341. Final Exam Tuesday, December 16, Problem 1 15 pts Problem 9 8 pts. Problem 2 5 pts Problem pts CEMISTRY 341 Final Exam Tuesday, December 16, 1997 Name NAID Problem 1 15 pts Problem 9 8 pts Problem 2 5 pts Problem 10 21 pts Problem 3 26 pts Problem 11 15 pts Problem 4 10 pts Problem 12 6 pts Problem

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 Tuning the Lewis Acidity of Boranes in rustrated Lewis Pair Chemistry: Implications for the Hydrogenation of Electron-Poor

More information

Name: Student Number: University of Manitoba - Department of Chemistry CHEM Introductory Organic Chemistry II - Term Test 2

Name: Student Number: University of Manitoba - Department of Chemistry CHEM Introductory Organic Chemistry II - Term Test 2 Name: Student Number: University of Manitoba - Department of Chemistry CHEM 2220 - Introductory Organic Chemistry II - Term Test 2 Thursday, March 12, 2015; 7-9 PM This is a 2-hour test, marked out of

More information

and phosphonyl-phosphinoyl analogues

and phosphonyl-phosphinoyl analogues Supporting Information for A new method for the synthesis of -aminoalkylidenebisphosphonates and their asymmetric phosphonylphosphinyl and phosphonyl-phosphinoyl analogues Anna Kuźnik, 1* Roman Mazurkiewicz,

More information

Supplementary Information for: E-H Bond Activations and Hydrosilylation Catalysis with Iron and Cobalt Metalloboranes

Supplementary Information for: E-H Bond Activations and Hydrosilylation Catalysis with Iron and Cobalt Metalloboranes Supplementary Information for: E-H Bond Activations and Hydrosilylation Catalysis with Iron and Cobalt Metalloboranes Mark A. Nesbit, Daniel L. M. Suess, Jonas C. Peters* Division of Chemistry and Chemical

More information

Supporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source

Supporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Supporting Information Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using

More information

CH Exam #4 (Take Home) Date Due: 11/25,26/2013

CH Exam #4 (Take Home) Date Due: 11/25,26/2013 CH2710 - Exam #4 (Take Home) Date Due: 11/25,26/2013 Section I - Multiple Choice - Choose the BEST answer from the choices given and place the letter of you choice in the space provided. 1. Energy absorbed

More information

Supplementary Information

Supplementary Information Electronic Supplementary Information for Dalton Transactions Insights into the Binding Properties of a Cuprous Ion Embedded in the Tren Cap of a Calix[6]arene and Supramolecular Trapping of an Intermediate.

More information

ORGANIC - BRUICE 8E CH MASS SPECT AND INFRARED SPECTROSCOPY

ORGANIC - BRUICE 8E CH MASS SPECT AND INFRARED SPECTROSCOPY !! www.clutchprep.com CONCEPT: PURPOSE OF ANALYTICAL TECHNIQUES Classical Methods (Wet Chemistry): Chemists needed to run dozens of chemical reactions to determine the type of molecules in a compound.

More information

Chem 2061 Final Exam. Fall Andy Aspaas, Instructor. Thursday, December 15, Instructions: Please print: Last name: First name:

Chem 2061 Final Exam. Fall Andy Aspaas, Instructor. Thursday, December 15, Instructions: Please print: Last name: First name: Please print: Last name: First name: hem 2061 Final Exam Fall 2005 Andy Aspaas, Instructor Thursday, December 15, 2005 Instructions: You may start as soon as you arrive. The exam was designed to be finished

More information

NMR = Nuclear Magnetic Resonance

NMR = Nuclear Magnetic Resonance NMR = Nuclear Magnetic Resonance NMR spectroscopy is the most powerful technique available to organic chemists for determining molecular structures. Looks at nuclei with odd mass numbers or odd number

More information

Chem 213 Final 2012 Detailed Solution Key for Structures A H

Chem 213 Final 2012 Detailed Solution Key for Structures A H Chem 213 Final 2012 Detailed Solution Key for Structures A H COMPOUND A on Exam Version A (B on Exam Version B) C 8 H 6 Cl 2 O 2 DBE = 5 (aromatic + 1) IR: 1808 cm 1 suggests an acid chloride since we

More information

[MnBrL(CO) 4 ] (L = Amidinatogermylene): Reductive Dimerization, Carbonyl Substitution, and Hydrolysis Reactions

[MnBrL(CO) 4 ] (L = Amidinatogermylene): Reductive Dimerization, Carbonyl Substitution, and Hydrolysis Reactions SUPPORTING INFORMATION (Organometallics, Ms. ID: om-2016-00168w) [MnBrL(CO) 4 ] (L = Amidinatogermylene): Reductive Dimerization, Carbonyl Substitution, and Hydrolysis Reactions Javier A. Cabeza,* Pablo

More information

MASS SPECTRA measure a compound s Mol. Wt. This ionization type is called: electron impact MS

MASS SPECTRA measure a compound s Mol. Wt. This ionization type is called: electron impact MS MASS SPECTRA measure a compound s Mol. Wt. p. 213 M + Molecule e - Molecule + 2 e - + + Mole cule + + Mol ecule IONIZATION CHAMBER repellor plate accelerating plates variable field magnet + Mo + lecule

More information

CSIR-UGC-NET/JRF GATE CHEMISTRY TEST : ORGANOMETALLIC COMPOUNDS

CSIR-UGC-NET/JRF GATE CHEMISTRY TEST : ORGANOMETALLIC COMPOUNDS 1 CSIR-UGC-NET/JRF GATE CHEMISTRY TEST : ORGANOMETALLIC MPOUNDS Time 00 : Hour Date : 1-10-2017 M.M. : 0 INSTRUCTION : 1. There are Two Parts. Part-A contains 10 objective type questions, each question

More information

CHEM 2430 Organic Chemistry I Fall Instructor: Paul Bracher. Final Examination

CHEM 2430 Organic Chemistry I Fall Instructor: Paul Bracher. Final Examination CHEM 2430 Organic Chemistry I Fall 2015 Final Exam Solutions Key Page 1 of 10 CHEM 2430 Organic Chemistry I Fall 2015 Instructor: Paul Bracher Final Examination Friday, December 11 th, 2015 12:00 1:50

More information

Supporting Information

Supporting Information Supporting Information An Alternative Approach to Synthesis of 3-(4-chloro butyl)-1h-indole -5-carbonitrile: A key intermediate of Vilazodone hydrochloride, an antidepressant drug Anitha N, Sudhakar Reddy

More information

Supplementary Information

Supplementary Information Supplementary Information NE Difference Spectroscopy: SnPh 3 CH (b) Me (b) C()CH (a) Me (a) C()N Me (d) Me (c) Irradiated signal Enhanced signal(s) (%) Me (a) Me (c) 0.5, Me (d) 0.6 Me (b) - Me (c) H (a)

More information

Phosphirenium-Borate Zwitterion: Formation in the 1,1-Carboboration Reaction of Phosphinylalkynes. Supporting Information

Phosphirenium-Borate Zwitterion: Formation in the 1,1-Carboboration Reaction of Phosphinylalkynes. Supporting Information Phosphirenium-Borate Zwitterion: Formation in the 1,1-Carboboration Reaction of Phosphinylalkynes Olga Ekkert, Gerald Kehr, Roland Fröhlich and Gerhard Erker Supporting Information Experimental Section

More information

a) 1. O 3 2. (CH 3 ) 2 S

a) 1. O 3 2. (CH 3 ) 2 S Name: 1 Chemistry 250B Final Exam December 19, 2008 Show non-zero formal charges on all atoms for all structures. There are 11 pages. 1. (42 pts) Complete the following reactions. Show the stereochemistry

More information

Supplementary Materials for

Supplementary Materials for www.advances.sciencemag.org/cgi/content/full/1/5/e1500304/dc1 Supplementary Materials for Isolation of bis(copper) key intermediates in Cu-catalyzed azide-alkyne click reaction This PDF file includes:

More information

I pledge on my honor that I have neither given nor received unauthorized aid on this examination

I pledge on my honor that I have neither given nor received unauthorized aid on this examination Chemistry 220b, Section 1 Exam 2 (100 pts) Thursday, ebruary 26, 2015 Chapters 13, 15-19 ame Write and sign the VU onor Pledge: I pledge on my honor that I have neither given nor received unauthorized

More information

CEM 852 Final Exam. May 5, 2011

CEM 852 Final Exam. May 5, 2011 CEM 852 Final Exam May 5, 2011 This exam consists of 8 pages. Please make certain that your exam has all of the necessary pages. Total points possible for this exam are 150. In answering your questions,

More information

Marking Scheme For The Exam QUESTION #

Marking Scheme For The Exam QUESTION # Chemistry 2420 S10 Spring 2005 Term Exam #2 110 Minutes Name: Student Number Marking Scheme For The Exam QUESTIN # 1 2 3 4 5 6 7 8 6 14 15 15 15 15 8 12 TTAL 100 % Question (6 Marks) A. Provide the structures

More information

c) Draw accurate tree diagrams for the A and X signals (10 Hz = 1 cm: use a ruler!).

c) Draw accurate tree diagrams for the A and X signals (10 Hz = 1 cm: use a ruler!). Practice Final CEM 393 Dr..M. Muchall Name Make sure that your exam has 10 pages. Show all work. Remember: a point a minute! Textbook (Pavia, Lampman, Kriz, Vyvyan, 4 th edition) and calculator allowed.

More information

CHM 292 Final Exam Answer Key

CHM 292 Final Exam Answer Key CHM 292 Final Exam Answer Key 1. Predict the product(s) of the following reactions (5 points each; 35 points total). May 7, 2013 Acid catalyzed elimination to form the most highly substituted alkene possible

More information

Massachusetts Institute of Technology Organic Chemistry Hour Exam #1. Name. Official Recitation Instructor

Massachusetts Institute of Technology Organic Chemistry Hour Exam #1. Name. Official Recitation Instructor Massachusetts Institute of Technology rganic Chemistry. Friday, September 0, 00 Prof. Timothy F. Jamison Hour Exam # Name (please both print and sign your name) fficial Recitation Instructor Directions:

More information

SDBS Integrated Spectral Database for Organic Compounds

SDBS Integrated Spectral Database for Organic Compounds SDBS Integrated Spectral Database for Organic Compounds Sample Search for Chemistry 130 Grace Baysinger and Dr. Dave Keller SDBS URL and Description http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng

More information

Physical Organic Chemistry (15 h)

Physical Organic Chemistry (15 h) Course code : CEM 43244 Course title : Advanced rganic Chemistry I Physical rganic Chemistry (15 h) Dr. Dinesh Pandithavidana E-mail: dinesh@kln.ac.lk Mobile: 0777-745-720 ffice: B1 222/3 Stereochemical

More information

I will not accept answers on scratch paper

I will not accept answers on scratch paper Final Exam March 19, 2013 rganic Chemistry 335 I will not accept answers on scratch paper This exam is 110 minutes long (8-9:50). I will post a key on D2L when I have all the exams back. There will be

More information

NUCLEAR MAGNETIC RESONANCE AND INTRODUCTION TO MASS SPECTROMETRY

NUCLEAR MAGNETIC RESONANCE AND INTRODUCTION TO MASS SPECTROMETRY NUCLEAR MAGNETIC RESONANCE AND INTRODUCTION TO MASS SPECTROMETRY A STUDENT SHOULD BE ABLE TO: 1. Identify and explain the processes involved in proton ( 1 H) and carbon-13 ( 13 C) nuclear magnetic resonance

More information

Exam 3 Chem 3045x Friday, December 5, 1997

Exam 3 Chem 3045x Friday, December 5, 1997 Exam 3 Chem 3045x Friday, December 5, 1997 Instructions: This is a closed book examination. You may not use any notes, books or external materials during the course of the examination. Please print your

More information

Supporting Information

Supporting Information Supporting Information Enantioselective Synthesis of 3-Alkynyl-3-Hydroxyindolin-2-ones by Copper-Catalyzed Asymmetric Addition of Terminal Alkynes to Isatins Ning Xu, Da-Wei Gu, Jing Zi, Xin-Yan Wu, and

More information

Welcome to Organic Chemistry II

Welcome to Organic Chemistry II Welcome to Organic Chemistry II Erika Bryant, Ph.D. erika.bryant@hccs.edu Class Syllabus 3 CHAPTER 12: STRUCTURE DETERMINATION 4 What is this solution Soda Tea Coffee??? 5 What is this solution Soda Tea

More information

Organic Chemistry CHM 224

Organic Chemistry CHM 224 rganic Chemistry CHM 224 Exam I Review Questions This set of questions is a compilation of old exams and additional questions, and does not represent the typical length of an exam - this is WAY longer!

More information

Chap 11. Carbonyl Alpha-Substitution Reactions and Condensation Reactions

Chap 11. Carbonyl Alpha-Substitution Reactions and Condensation Reactions Chap 11. Carbonyl Alpha-Substitution eactions and Condensation eactions Four fundamental reactions of carbonyl compounds 1) Nucleophilic addition (aldehydes and ketones) ) Nucleophilic acyl substitution

More information

INTRODUCTORY ORGANIC CHEMISTRY II --- PROBLEM SET #2

INTRODUCTORY ORGANIC CHEMISTRY II --- PROBLEM SET #2 CHEM 222 Section 01 Fall 2007 Dr. C. Rogers Page 1 of 5 INTRDUCTRY RGANIC CHEMISTRY II --- PRBLEM SET #2 DISTRIBUTED: Thurs.Nov.15 th. CMPLETIN DEADLINE: Thurs.Nov.29 th @ 10:15am. INSTRUCTINS: Work through

More information

Proton NMR. Four Questions

Proton NMR. Four Questions Proton NMR Four Questions How many signals? Equivalence Where on spectrum? Chemical Shift How big? Integration Shape? Splitting (coupling) 1 Proton NMR Shifts Basic Correlation Chart How many 1 H signals?

More information

Objective 4. Determine (characterize) the structure of a compound using IR, NMR, MS.

Objective 4. Determine (characterize) the structure of a compound using IR, NMR, MS. Objective 4. Determine (characterize) the structure of a compound using IR, NMR, MS. Skills: Draw structure IR: match bond type to IR peak NMR: ID number of non-equivalent H s, relate peak splitting to

More information

Chemistry I (Organic) Aromatic Chemistry. LECTURE 4 Electrophilic Substitution (part 3)

Chemistry I (Organic) Aromatic Chemistry. LECTURE 4 Electrophilic Substitution (part 3) 1 Chemistry I (Organic) Aromatic Chemistry LCTU 4 lectrophilic Substitution (part 3) Alan C. Spivey a.c.spivey@imperial.ac.uk Dec 2009 2 Format and scope of presentation lectrophilic aromatic substitution

More information

Cationic 5-Phosphonio Substituted N-heterocyclic Carbenes

Cationic 5-Phosphonio Substituted N-heterocyclic Carbenes Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Cationic 5-Phosphonio Substituted N-heterocyclic Carbenes Kai Schwedtmann, a Robin Schoemaker,

More information

2 Answer all the questions. 1 The first commercially useful azo dye was chrysoidine, designed by Otto Witt in H 2 N. chrysoidine.

2 Answer all the questions. 1 The first commercially useful azo dye was chrysoidine, designed by Otto Witt in H 2 N. chrysoidine. 2 Answer all the questions. 1 The first commercially useful azo dye was chrysoidine, designed by Otto Witt in 1875. N N NH 2 H 2 N chrysoidine (a) Witt made this dye by first forming the diazonium salt

More information

Tetrahydroquinolines by multicomponent Povarov reaction in water: Calix[n]arene-catalysed and mechanistic insights

Tetrahydroquinolines by multicomponent Povarov reaction in water: Calix[n]arene-catalysed and mechanistic insights Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 219 Tetrahydroquinolines by multicomponent Povarov reaction in water: Calix[n]arene-catalysed

More information

CHEM 3.2 (AS91388) 3 credits. Demonstrate understanding of spectroscopic data in chemistry

CHEM 3.2 (AS91388) 3 credits. Demonstrate understanding of spectroscopic data in chemistry CHEM 3.2 (AS91388) 3 credits Demonstrate understanding of spectroscopic data in chemistry Spectroscopic data is limited to mass, infrared (IR) and 13 C nuclear magnetic resonance (NMR) spectroscopy. Organic

More information

Supplementary Information. Mapping the Transmission Function of Single-Molecule Junctions

Supplementary Information. Mapping the Transmission Function of Single-Molecule Junctions upplementary Information Mapping the Transmission Function of ingle-molecule Junctions Brian Capozzi 1, Jonathan Z. Low 2, Jianlong Xia 3, Zhen-Fei Liu 4, Jeffrey B. Neaton 5,6, Luis M. Campos 2, Latha

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002 Supporting Information for Angew. Chem. Int. Ed. Z19280 Wiley-VCH 2002 69451 Weinheim, Germany A New Method for Determining the Difference in Relative Apicophilicity of Carbon Substituents of 10-P-5 Phosphoranes:

More information

Department of Chemistry SUNY/Oneonta. Chem Organic Chemistry I. Examination #4 - December 9, 2002 ANSWERS

Department of Chemistry SUNY/Oneonta. Chem Organic Chemistry I. Examination #4 - December 9, 2002 ANSWERS INSTRUCTINS Department of Chemistry SUNY/neonta Chem 221 - rganic Chemistry I Examination #4 - December 9, 2002 ANSWERS This examination is in multiple choice format; the questions are in this Exam Booklet

More information

CHEM Chapter 12 Infrared and Mass Spec (homework). Stafford. S18

CHEM Chapter 12 Infrared and Mass Spec (homework). Stafford. S18 Exhibit 12-4 The following question(s) refer to the mass spectrum shown below. 1. Refer to Exhibit 12-4. This compound contains C, H, and one other atom. Identify the other atom from the mass spectrum

More information

guanidine bisurea bifunctional organocatalyst

guanidine bisurea bifunctional organocatalyst Supporting Information for Asymmetric -amination of -keto esters using a guanidine bisurea bifunctional organocatalyst Minami Odagi* 1, Yoshiharu Yamamoto 1 and Kazuo Nagasawa* 1 Address: 1 Department

More information

Measuring enzyme (enantio)selectivity

Measuring enzyme (enantio)selectivity Measuring enzyme (enantio)selectivity Types of selectivity - review stereoisomers Stereoselective synthesis (create) vs. resolutions (separate) Enantioselectivity & enantiomeric purity Ways to measure

More information

Simple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their Labile Dimethylsulfide Adducts

Simple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their Labile Dimethylsulfide Adducts Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information for: Simple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their

More information

Technique Experiment 1-1

Technique Experiment 1-1 Chemistry 335. Technique Experiment 1A: Separation of Benzoin and Benzil Name: Date: Benzoin 1. Physical Properties (5 points) Color R f TLC Mobile Phase Amount isolated (mg) Mass recovery (%) 2. IR Spectrum

More information

Spectroscopy. Empirical Formula: Chemical Formula: Index of Hydrogen Deficiency (IHD)

Spectroscopy. Empirical Formula: Chemical Formula: Index of Hydrogen Deficiency (IHD) Spectroscopy Empirical Formula: Chemical Formula: Index of Hydrogen Deficiency (IHD) A)From a structure: B)From a molecular formula, C c H h N n O o X x, Formula for saturated hydrocarbons: Subtract the

More information

Learning Guide for Chapter 13 - Alkynes

Learning Guide for Chapter 13 - Alkynes Learning Guide for Chapter 13 - Alkynes I. Introduction to Alkynes - p 1 II. Natural ccurrence and Uses of Alkynes - p 5 III. Physical Properties of Alkynes - p 7 IV. Spectroscopy of Alkynes - p 7 V. Nomenclature

More information

Supporting Information

Supporting Information Supporting Information Lewis acid-catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates Vincent Tran and Thomas G. Minehan * Department of Chemistry and

More information

ALDEHYDES AND KETONES

ALDEHYDES AND KETONES ALDEHYDES AND KETONES IN WEEK 1, A STUDENT SHOULD BE ABLE TO: 1. Give the IUPAC name given the structure, and draw the structure given the name, of aldehydes and ketones. Also, draw the structure given

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2019 Supporting Information Difluorocarbene-derived trifluoromethylselenolation of benzyl halides Xin-Lei

More information

Interpretation of Organic Spectra. Chem 4361/8361

Interpretation of Organic Spectra. Chem 4361/8361 Interpretation of Organic Spectra Chem 4361/8361 Characteristics of Common Spectrometric Methods H-1 C-13 MS IR/RAMAN UV-VIS ORD/CD X- RAY Radiation type RF RF Not relevant IR UV to visible UV to visible

More information

Exam I 19 April 2004 Name:

Exam I 19 April 2004 Name: Chem 317 S04 Page 1 of 7 Kantorowski Exam I 19 April 2004 Name: This exam contains 6 pages of questions confirm this once you begin The last page is a spectral data table that can be removed You will have

More information

Tautomerism in 1-hydroxy-2-naphthaldehyde Schiff bases: Calculation of tautomeric isomers using carbon-13 NMR

Tautomerism in 1-hydroxy-2-naphthaldehyde Schiff bases: Calculation of tautomeric isomers using carbon-13 NMR Spectroscopy 17 (2003) 747 752 747 IOS Press Tautomerism in 1-hydroxy-2-naphthaldehyde Schiff bases: Calculation of tautomeric isomers using carbon-13 NMR Salman R. Salman a and Fadhil S. Kamounah b, a

More information

Supporting Information. N719 Dye-Sensitized Organophotocatalysis: Enantioselective Tandem Michael Addition/Oxyamination of Aldehydes

Supporting Information. N719 Dye-Sensitized Organophotocatalysis: Enantioselective Tandem Michael Addition/Oxyamination of Aldehydes Supporting Information N719 Dye-Sensitized Organophotocatalysis: Enantioselective Tandem Michael Addition/Oxyamination of Aldehydes Hyo-Sang Yoon, Xuan-Huong Ho, Jiyeon Jang, Hwa-Jung Lee, Seung-Joo Kim,

More information

Chem 454 instrumental Analysis Exam 1 February 6 th, 2008

Chem 454 instrumental Analysis Exam 1 February 6 th, 2008 Chem 454 instrumental Analysis Exam 1 February 6 th, 2008 1 Name: 1] A glass electrode was immersed into a solution of ph 4.33 gave a response of 677.1 mv. This electrode was used to measure a sample solution

More information

Supporting Information. Enantioselective Pd-Catalyzed Allylation Reaction of Fluorinated Silyl Enol Ethers

Supporting Information. Enantioselective Pd-Catalyzed Allylation Reaction of Fluorinated Silyl Enol Ethers S1 Supporting Information Enantioselective Pd-Catalyzed Allylation Reaction of luorinated Silyl Enol Ethers Étienne Bélanger, Katy Cantin, livier Messe, Mélanie Tremblay, and Jean-rançois Paquin* Canada

More information

Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids

Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids Copper-Catalyzed xidative Cyclization of Carboxylic Acids Supplementary material (51 pages) Shyam Sathyamoorthi and J. Du Bois * Department of Chemistry Stanford University Stanford, CA 94305-5080 General.

More information

CHEM 241 UNIT 5: PART A DETERMINATION OF ORGANIC STRUCTURES BY SPECTROSCOPIC METHODS [MASS SPECTROMETRY]

CHEM 241 UNIT 5: PART A DETERMINATION OF ORGANIC STRUCTURES BY SPECTROSCOPIC METHODS [MASS SPECTROMETRY] CHEM 241 UNIT 5: PART A DETERMINATION OF ORGANIC STRUCTURES BY SPECTROSCOPIC METHODS [MASS SPECTROMETRY] 1 Introduction Outline Mass spectrometry (MS) 2 INTRODUCTION The analysis of the outcome of a reaction

More information

Chapter 9. Nuclear Magnetic Resonance. Ch. 9-1

Chapter 9. Nuclear Magnetic Resonance. Ch. 9-1 Chapter 9 Nuclear Magnetic Resonance Ch. 9-1 1. Introduction Classic methods for organic structure determination Boiling point Refractive index Solubility tests Functional group tests Derivative preparation

More information

Final Exam. Your lab section and TA name: (if you are not in a lab section write no lab ) Instructions:

Final Exam. Your lab section and TA name: (if you are not in a lab section write no lab ) Instructions: CHEM 232 Final Exam May 10, 2014 RedID number: Signature: Your lab section and TA name: (if you are not in a lab section write no lab ) Instructions: 1. In fairness to all, do not open this test until

More information

Understanding the function of cetyltrimethyl ammonium bromide in Lithium/Sulfur Cells

Understanding the function of cetyltrimethyl ammonium bromide in Lithium/Sulfur Cells Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A. This journal is The Royal Society of Chemistry 2017 Supporting Information Understanding the function of cetyltrimethyl ammonium

More information

CHEM J-10 June The structure of ( )-linalool, a commonly occurring natural product, is shown below.

CHEM J-10 June The structure of ( )-linalool, a commonly occurring natural product, is shown below. CEM1102 2014-J-10 June 2014 The structure of ( )-linalool, a commonly occurring natural product, is shown below. 4 What is the molecular formula of ( )-linalool? C 10 18 O Which of the following best describes

More information

Chemistry 333. Final Examination

Chemistry 333. Final Examination Chemistry 333 Final Examination December 9, 2010 Professor Charonnat Be certain that your examination has eleven (11) pages including this one. Put your name on each page of this examination booklet. By

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry

More information

NMR Spectroscopy: Determination of Molecular Structures

NMR Spectroscopy: Determination of Molecular Structures Experiment 2 NMR Spectroscopy: Determination of Molecular Structures Reading: Handbook for Organic Chemistry Lab, chapters on NMR Spectroscopy (Chapter 18) and Identification of Compounds (Chapter 20).

More information

Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures

Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures Supporting Information Low Temperature n-butyllithium-induced [3,3]-Sigmatropic Rearrangement/Electrophile Trapping Reactions of Allyl-1,1- Dichlorovinyl Ethers. Synthesis of - - and -lactones. Aaron Christopher

More information

CHEM 213 FALL 2018 MIDTERM EXAM 2 - VERSION A

CHEM 213 FALL 2018 MIDTERM EXAM 2 - VERSION A CEM 213 FALL 2018 MIDTERM EXAM 2 - VERSIN A Answer multiple choice questions on the green computer sheet provided with a PENCIL. Be sure to encode both your NAME and Registration Number (V#). You will

More information