Minnesota - AH - 3401

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Exercise: SN2 MechanismsMonday, February 23For each of the SN2 reactions below: (i) identify the nucleophile and the leaving group; (ii) push electrons, using curved arrows, to illustrate the reaction mechanism; and (iii)

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Solutions: SN2 MechanismsMonday, February 23Important: each of your curved arrows should begin at a pair of electrons, and should end at a nucleus that the pair will be newly associated with.H3C HSCH3+C H HClHS

Minnesota - AH - 3401

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Solutions: Proton-Mediated SN1 MechanismsFriday, February 27H3 C C H 3C H 3C BrCH 3OHH3 C C H3 C H 3C O CH 3(heat )H3 C C H 3C H3C BrCH3Br H OH3 C C H3 C H 3C OHBrH 3C CH 3CH 3CH 3H3 C C H3 C H 3

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 12 Chemotheraputic Alkylating AgentsFriday, February 27Though there are many types of cancer, cancerous cells have two characteristics in common: (1) they multiply more rapidly than normal cells, resulting in tumor growth;

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 13 Multistep Reaction MechanismsFriday, February 27Diethylamine [(CH3)2NH] is a great nucleophile, and alkyl halides like methyl iodide (CH3I) add to it readily via the SN2 mechanism. One interesting characteristic of this

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 12 Solutions Chemotheraputic Alkylating AgentsFriday, February 27a)very reactiveN N Nvery reactiveOsomewhat reactiveH2Nvery N reactiveNH O NH2somewhat reactiveNThese molecules have three types of lone pa

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 13 Solutions Multistep Reaction MechanismsFriday, February 27H H 3C N H 3C H C H H H 3C I1st additionH 3C N+ I CH 3 H O O OO + H3C N H3C CH 3 CH 3 + I2nd additionH 3C N H 3C CH 3HO H H C HOIAnother way th

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Exercise: Stereoselectivity of E2Monday, March 2Each of the diastereomeric 2,3-dibromobutanes below reacts via E2 elimination to give a different alkene product. (For this problem, consider only elimination at the C2-C3 bo

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Exercise: E2 Reactions with Multiple ProductsWednesday, March 41. E2 elimination of 1-bromo-trans-1,2-dimethylcyclohexane (shown below) should yield three different alkene products, by deprotonation of three different Hs i

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 14 Predicting Reaction OutcomesFriday, March 6Predict the starting materials, reagents or products in the following reactions; put one molecule in each box. (Stereoisomers count as separate molecules.) If there are multipl

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 15 Drawing Potential Energy DiagramsFriday, March 6The reaction shown below proceeds by SN1 to give two products: one (P1) by normal substitution, and the other (P2) involving 1,2-hydride shift of the intermediate cation.

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 14 Solutions Predicting Reaction OutcomesFriday, March 6Predict the starting materials, reagents or products in the following reactions; put one molecule in each box. (Stereoisomers count as separate molecules.) If there a

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 15 Solutions Drawing Potential Energy DiagramsO HO I CH 3 O O CH 3Friday, March 6OCH3 O+SMP1P2a.IOH OI HHCH 3SMI1IHOH O CH 3 OOO O CH 3CH 3P1H+P1So, the potential energy curve for

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Solutions: Planning Multistep Organic SynthesesFriday, March 13H 3C H3CH CH 3H3C H 3CSCH 2CH3 CH 3H 3C H3 CH CH 3Br 2 hH 3C H3 CBr CH 3CH 3 CH 2SHH 3C H3 CSCH2 CH 3 CH 3(but will have to separate

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 16 Unpaired Electron PushingFriday, March 13In class, we explained that allylic bromination is usually performed with Nbromosuccinimide (NBS), in order to avoid the bromine addition to the double bond that would occur if t

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 16 Solutions Unpaired Electron PushingFriday, March 13a. First product:H HR+HHROOBr HN Br O+N(serves as R in subsequent cycles)OSecond product:OresonanceBrN(f rom mechanism above)OO

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Exercise: Choosing Between Multiple Synthetic RoutesFriday, March 27a. Show how either syn- or anti-dihydroxylation could be used to make the molecule below from alkene starting materials. b. If the only molecules we had t

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Exercise: Choosing Between Multiple Synthetic RoutesFriday, March 27HO(R)H CH 3recipe:(R)recipe:mCPBA, H2OH H 3COHKMnO4, H2O/-OH(+ enantiomer) anti-dihydroxylation syn-dihydroxylationH H 3CH CH3an alk

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 17 More Multistep Organic SynthesisFriday, March 27As we did in the In-Class Exercise, Planning Multistep Organic Syntheses, propose a multistep synthesis for each of the transformations below, giving a recipe of reagents

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 18 Diastereoselectivity in Organic SynthesesFriday, March 27Many pharmaceutically active substances have lots of stereocenters, and as we discussed in Chapter 5 (Stereochemistry), the correct placement of these stereocente

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 19 Diverted Alkene Addition MechanismsFriday, March 27In each of the pairs of reactions below, the first reaction is a standard reaction that looks very much like what weve covered in class, and the second reaction diverge

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 17 Solutions: More Multistep Organic SynthesisFriday, March 27ClA challenge in both of these problems is to use the few reactions you know to make what you want. (You might imagine this issue could be resolved for profes

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 18 Solutions Diastereoselectivity in Organic SynthesesFriday, March 27H 3C H3C XH3CORCH3 CH 2 OHCH3 CH 2 OH XCH 3 O X CH 3KMnO4, H2O/-OHmCPBA, H2OH3CCH 3 O XX H3C OH H 3C CH3 CH2 OH H 3C OH H3 C CH3 CH 2

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 19 Solutions Diverted Alkene Addition MechanismsFriday, March 27Br Br 2H (+ enantiomer) H 3C BrBrBr H Br OR H H3 C CH3 BrBr (also draw as H Br + + ; comes in f rom behind C-Br bond (SN2) H H3 C partial charge bette

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Exercise: Alkynes in SynthesisWednesday, April 1Alkynes are useful building blocks for organic chemists because different molecular parts can be attached to them by nucleophilic addition reactions. The synthesis below illu

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 20 Interfering Functional GroupsFriday, April 3Complex organic molecules frequently have multiple functional groups, and it is sometimes challenging to design organic syntheses such that transformations of one functional g

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 21 Retrosynthetic AnalysisFriday, April 3Sometimes it is easier to think about organic synthesis in reverse, by disconnecting a complex molecule into simple parts that you know how to reconnect synthetically. Organic chemi

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 20 Solutions Interfering Functional GroupsFriday, April 3KMnO 4 H3C H 2O/- OH H3CHOOHKMnO4 will react with the alkyne too. Its not clear how far the alkyne will be oxidized; milder conditions than these (pH 7) would

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 21 Solutions Retrosynthetic AnalysisFriday, April 3There are many correct answers to each of these problems, only a few of which are shown below.can make from alkyne, or by ozonolysisO O H CH31. Sia2BH 2. H2O2/-OH (a

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 22 Alcohols from Alkylmetal ReagentsFriday, April 10Show how each of the alcohols one the right could be synthesized from at least one alkyl halide and a carbonyl-containing molecule as starting materials. A challenge: Mak

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 22 Solutions Alcohols from Alkylmetal ReagentsFriday, April 10Unless Ive indicated specifically that only one alkylmetal reagent is possible, either alkyllithiums or Grignard reagents can be used. (They are interchangeable

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 23 Diagnostic Tests Based on Oxidation and ReductionFriday, April 17Biomedical diagnostic testsused to detect the levels of specific molecules in bodily fluids such as blood or urineare frequently based on detecting the sp

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 24 Mechanisms with Nucleophilic Attack on CarbonylsFriday, April 17Write mechanisms for the following transformations involving carbonyl groups.OMgBrOMgBr+O O(excess)O O1. LiAlH4 2. H3O+OHOH

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 23 Solutions Diagnostic Tests Based on Oxidation and ReductionFriday, April 17H OH H O HO HO H H OH OH Hglucose oxidaseH OH H O HO HO H H OHREDUCTIONorOXIDATIONOor(-H2)NEITHERglucosegluconolactoneAs yo

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 24 Solutions Mechanisms with Nucleophilic Attack on CarbonylsFriday, April 17OMgBrOMgBr+O OOMgBr OO MgBr O OOO OMgBrO OMgBrBrMg OOMgBrOBrMgOMgBrO O1. LiAlH4 2. H3O+OHOHH H Al

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 25 Functional Group Interconversion with TosylatesFriday, April 24Although the syntheses below look simpleeach just involves changing a functional group into a new onethey all require multiple steps, and tosylation is a us

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 26 Equivalent and Inequivalent NucleiFriday, April 24For each of the molecules below, Label each inequivalent set of protons with a lower-case letter (a, b); In the box, write the number of resonances you would expect to

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 25 Solutions Functional Group Interconversion with TosylatesFriday, April 24OIONaBH4, EtOHOHTsCl, pyridineOTsNaIICH3 CH 3CH2H OHCH 3CH 2HCH 3 CH 2CH 2CH3backside attack, inversionCH 3 C CCH3 C

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 26 Solutions Equivalent and Inequivalent NucleiFriday, April 24number of resonancesH ClaHHCHa Ha Hbnumber of resonancesbHb Cl2b4H H H H a a a aH c HdH cH ClbHb Br3bHaHCHa Ha HbHa

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Exercise: IR Spectroscopy and MS Fragmentation PatternsFriday, May 1Cladosporium resinae, sometimes called fuel fungus, colonizes aircraft fuel lines in wet climates. To use aircraft fuel as food, the fungus must first oxi

Minnesota - CHEM - 2301

Chemistry 2301 In-Class Exercise Solutions: IR Spectroscopy and MS Fragmentation PatternsFriday, May 1a. IR spectra are typically interpreted by looking at characteristic resonances in the 1600-3600 cm-1 range of the spectrum; the region lower th

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 27 Complex Splitting Patterns in NMRFriday, May 1This Workshop deals with the NMR spectrum of vinyl acetate, shown below. The lower two spectra are close-ups from the upper spectrum.O H H O CH 3 H31 1187651

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 28 Structure Determination with NMRFriday, May 1Morgan, a chemist, had planned to use 1,2-dibromo-1-ethoxyethane (drawn below) as a starting material in a substitution reaction. However, he found that even weak Lewis bases

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 27 Solutions Complex Splitting Patterns in NMRFriday, May 1When we covered complex splitting patterns in lecture, I showed the simplest complex splitting pattern (if you will), the doublet of doublets; I also showed that t

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 28 Solutions Structure Determination with NMRFriday, May 1The problem tells us that the decomposition reaction is an elimination reaction, in which one of the two Br atoms acts as a leaving group. It's not clear from the p

Minnesota - CHEM - 2301

Exact Masses and Molecular Formulae12Cmass set to 12 amu, exactly.As a result, 1H mass is actually higher than 1 amu. amu And 16O mass is lower than 16 l th amu. Isotopes vary from unit masses by mass defect. I t f it b d f t1Hhas positive m

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 29 Using IR, MS and NMR Data for Structure ElucidationFriday, May 8Fragrance chemists frequently use spectroscopic tools to try to determine what molecules are responsible for a particular natural scentso that, say, the sm

Minnesota - CHEM - 2301

Chemistry 2301 Workshop 29 Solutions Using IR, MS and NMR Data for Structure Elucidation a.Elemental Composition Calculator v1.0 Calculations for : monoisotopic mass atom C H N O S P mass 12.0000 1.0078 14.0030 15.9949 31.9720 30.9737 min 0 0 0 0 0

Minnesota - CHEM - 2301

NAME _ID #_ORGANIC CHEMISTRY I (2301-003) 1:25 2:15 pm, February 16, 2009 Exam 1When the exam begins, write your name at the top of each page. You may use pen or pencil. However, re-grades will be considered only for exams completed in pen.

Minnesota - CHEM - 2301

Chemistry 2301 Exam 1 Answer Key Exam 1 Mean: Exam 1 Median: Exam 1 St. Dev.: 77 80 14Monday, February 16, 2009FrequencyExam Grade11. (9 pts) Draw Lewis dot structures for each of the molecules below. Draw all valence electrons as dots. If

Binghamton - CS - 220

1: d)2: c)3: c)4: d)

Binghamton - CS - 220

CS 220: Computer Systems II: Architecture and ProgrammingSpring 2009 - Section A0Quiz #7 - 2009/04/27 Name: _=1:Circle which one (1) of the following is the term for the processor feature which allows a system to appear to be able to us

Minnesota - CHEM - 2301

NAME _UM Internet ID_ORGANIC CHEMISTRY I (2301-001) 9:05 9:55 am, February 18, 2008 Exam 1When the exam begins, write your name at the top of the first two pages. You may use pen or pencil. However, re-grades will be considered only for exams

Binghamton - CS - 220

1: b)2: c), d)3: b)4: g), h)

Minnesota - CHEM - 2301

NAME _ID #_ORGANIC CHEMISTRY I (2301-003) 1:25 2:15 pm, October 1, 2007 Exam 1When the exam begins, write your name at the top of the first two pages. You may use pen or pencil. However, re-grades will be considered only for exams completed

Binghamton - CS - 220

CS 220: Computer Systems II: Architecture and ProgrammingSpring 2009 - Section A0Quiz #8 - 2009/05/04 Name: _=1:Circle which of the following (it could be any number of them) aretrue statements about key-pair type encryption systems:

Minnesota - CHEM - 2301

Chemistry 2301 Exam 1 Answer KeyMonday, February 18, 2007Exam 1 Mean: Exam 1 Median: Exam 1 St. Dev.:78 80 1511. (9 pts) Draw Lewis dot structures for each of the molecules below. Draw all valence electrons as dots. If there are formal char

Binghamton - CS - 220

1: a), c), e)2.1: a)2.2: b)2.3: a)2.4: c)2.5: b)3: a), d)4: c)

Binghamton - CS - 220

CS 220: Computer Systems II: Architecture and ProgrammingSpring 2009 - Section A0Final Exam - 2009/05/11 Name: _=1:Circle which of the flags (it can be any number of them) listed undereach set of numbers will be set (to 1) after each pa