Oxidations (Pinnick & Jones) - Carboxylic Acids (IOC 25) That Chemist (old) 2022-04-10 | In this episode, I discuss Jones Oxidation, Pinnick Oxidation, and Tollen's test.*The slide titled ‘Pinnick Oxidation’ has a typo - underneath the reaction arrow it should say NaH2PO4, not NaH2PO3*----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:first Jones - doi.org/10.1016/0223-5234(94)90113-9second Jones - doi.org/10.1134/S1070428018060040first Pinnick - doi.org/10.1002/anie.201606679second Pinnick - doi.org/10.1016/j.tet.2015.07.036----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
The Popcorn Pillow (Patreon Chempilation #7) That Chemist (old) 2023-04-25 | Please support the channel on Patreon if you would like to see more! This was the Patreon video from February 2023. patreon.com/thatchemist
New Channel (Channel Update) That Chemist (old) 2022-05-22 | Please subscribe to the new channel! youtube.com/channel/UC0nEDA3uRd5YuvBfMwQNteg
ChemDraw Design Elements That Chemist (old) 2022-05-21 | In this video, I show you how to use and manipulate design elements in ChemDraw! I also discuss how to use templates, use your own templates, and move figures from ChemDraw into Microsoft Word & Microsoft PowerPoint.patreon.com/thatchemistCommunity Discord - discord.gg/QWNPETtPcZ
Transesterification of Thionoesters That Chemist (old) 2022-05-20 | In this video, I discuss my first big project from my PhD - the transesterification of thionoesters.patreon.com/thatchemistCommunity Discord: discord.gg/QWNPETtPcZ----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:Crown Ether Paper - doi.org/10.1021/jo00164a001Reynaud, P.; Richard, H.; Menard, G.; Valette, G.; Morin, H. O-Dialkylaminoalkyl Thioesters, Analogs of Adiphenine and Related Esters. Eur. J. Med. Chem. 1975, 10 (3), 262−267.Orthoester Paper - doi.org/10.1055/s-1989-27356Transesterification - doi.org/10.1021/acs.joc.8b02260Paper with other examples - doi.org/10.1002/chem.201904132----------------------------------------------------------------------------------------------------------------------------------
Chaos and Order - Methods of Purification That Chemist (old) 2022-05-17 | In this video, I discuss the different methods that are available to purify molecules based on their differing physical properties.I messed up when I defined HPLC - it is an abbreviation of High Performance Liquid Chromatographypatreon.com/thatchemistCommunity Discord - discord.gg/QWNPETtPcZ
ChemDraw Tips & Tricks That Chemist (old) 2022-05-16 | In this video, I show you how to align figures, clean up structures, and clean up reactions in ChemDraw! I also discuss how to copy structures from ChemDraw and paste them into Reaxys/Scifinder. I also discuss how to get exact mass data for HRMS, and predict 1H and 13C NMRs.Totally Synthetic Style Sheet:web.archive.org/web/20150515004720/http://totallysynthetic.com/blog/?page_id=287patreon.com/thatchemistCommunity Discord - discord.gg/QWNPETtPcZ
Diazo Synthesis (IOC 48) That Chemist (old) 2022-05-15 | In this episode, I discuss the synthesis of diazo compounds using diazo transfer, from hydrazones, as well as through diazotization!patreon.com/thatchemistCommunity Discord: discord.gg/QWNPETtPcZ ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:practice problem 1 - doi.org/10.1016/S0040-4039(98)01465-8practice problem 2 - doi.org/10.1021/jo00302a027practice problem 3 - doi.org/10.1016/S0040-4039(01)02368-1diazo review - doi.org/10.1021/acs.chemrev.5b001211st diazo transfer - doi.org/10.1016/j.tetlet.2014.03.1152nd diazo transfer - doi.org/10.1055/s-0039-16909053rd diazo transfer - doi.org/10.1016/j.tet.2014.05.0544th diazo transfer - doi.org/10.1055/s-0036-15881741st hydrazone - doi.org/10.3762/BJOC.17.472nd hydrazone - doi.org/10.1016/j.tetlet.2011.01.1163rd hydrazone - doi.org/10.1016/j.tetlet.2020.1522674th hydrazone - doi.org/10.1021/acscatal.1c002641st diazotization - doi.org/10.1016/j.tet.2012.03.0222nd diazotization - doi.org/10.1016/S0960-894X(02)00241-X3rd diazotization - doi.org/10.1016/j.jfluchem.2021.1098994th diazotization - doi.org/10.1016/j.tetlet.2009.03.118---------------------------------------------------------------------------------------------------------------------------
Ketols & Related Rearrangements (IOC 47) That Chemist (old) 2022-05-13 | In this episode, I discuss 1,2-shifts of ketols and related compounds, in reactions such as Criegee rearrangement, alpha ketol rearrangement, and benzilic acid rearrangement!patreon.com/thatchemistCommunity Discord: discord.gg/QWNPETtPcZ ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:3rd practice problem - doi.org/10.1021/jo9603338OG Büchner–Curtius–Schlotterbeck - doi.org/10.1002/cber.188501802118OG Criegee - doi.org/10.1002/cber.194507709121st Criegee - doi.org/10.1021/ja01163a0722nd/3rd Criegee - doi.org/10.1021/jo00097a006orthoester - doi.org/10.3998/ark.5550190.0006.412Criegee review - doi.org/10.3762/bjoc.12.162(maybe) OG alpha-ketol - doi.org/10.1002/prac.18860340101 1st ketol - doi.org/10.1016/0039-128X(91)90068-72nd ketol - doi.org/10.1016/S0040-4039(01)94374-63rd ketol - doi.org/10.1039/C9GC00336C4th ketol - doi.org/10.3987/COM-98-S(H)63amazing ketol review - doi.org/10.1002/0471264180.or062.03OG Benzilic - doi.org/10.1002/jlac.183802501021st benzilic - doi.org/10.1021/jm00368a0092nd benzilic - doi.org/10.1021/jacs.5b015173rd benzilic - doi.org/10.1039/C2OB26737C4th benzilic - doi.org/10.1039/C3RA42929F 1st practice - doi.org/10.1016/S0040-4039(98)01465-82nd practice - doi.org/10.1021/jo00302a0273rd practice - doi.org/10.1016/S0040-4039(01)02368-1---------------------------------------------------------------------------------------------------------------------------
My Minecraft Periodic Table That Chemist (old) 2022-05-13 | I built the entire periodic table in Minecraft! It is based on the 2020 ACS periodic table throw blanket.
Aza-Baeyer-Villiger & Related Reactions (IOC 46) That Chemist (old) 2022-05-11 | In this episode, I discuss 1,2-shifts of nitrogen containing motifs, including oximes, hydroxylamines, and azides! I discuss Beckmann rearrangement, the Semmler-Wolff reaction, Schmidt rearrangement, Stieglitz rearrangement, Demjanov rearrangement, as well as Tiffeneau Demjanov rearrangement.patreon.com/thatchemistCommunity Discord: discord.gg/QWNPETtPcZThe last reaction is technically the Büchner–Curtius–Schlotterbeck Reaction... ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:OG Beckmann - doi.org/10.1002/cber.1886019012221st Beckmann - doi.org/10.1021/ja01584a0332nd Beckmann - doi.org/10.1021/jacs.8b016183rd Beckmann - doi.org/10.1021/acs.joc.8b01810OG Semmler-Wolff - doi.org/10.1002/cber.1892025022001st Semmler - doi.org/10.1021/ja034842k 2nd Semmler - doi.org/10.1080/00397919408011748OG Schmidt - doi.org/10.1002/cber.192405704231st Schmidt - doi.org/10.1055/s-0037-16103122nd Schmidt - doi.org/10.1016/j.bmc.2015.07.0363rd Schmidt - doi.org/10.1016/j.bmcl.2015.02.0444th Schmidt - doi.org/10.1021/ja00315a030OG Stieglitz - doi.org/10.1021/ja02179a0081st Stieglitz - doi.org/10.1021/jo00940a0302nd Stieglitz - doi.org/10.1021/ja02269a0143rd Stieglitz - doi.org/10.1021/jo01159a0154th Stieglitz - doi.org/10.1021/ja02267a019Lycopodine - doi.org/10.1021/ja980117bOG Demjanov - Demjanov, N. J.; Lushnikov, M. J. Russ. Phys. Chem. Soc. 1903, 35, 26–42 (I couldn’t find a DOI)1st Demjanov - doi.org/10.1007/BF009496052nd Demjanov (Corey Cortistatins)- doi.org/10.1021/ol802328n OG Tiffeneau - Marc Tiffeneau; Paul Weill; Bianca Tchoubar. Comptes Rendus. 205: 54–56. (1937). (I couldn’t find a DOI) 1st Tiffeneau - doi.org/10.1039/C6CC01149G 2nd Tiffeneau - doi.org/10.1021/jo50061253rd Tiffeneau - doi.org/10.1021/jacs.8b06835Bonus Tiffeneau - doi.org/10.1055/s-0039-1690047 Practice problem 3 - doi.org/10.1021/jo9603338---------------------------------------------------------------------------------------------------------------------------
Ketenes & Related Rearrangements (IOC 45) That Chemist (old) 2022-05-09 | In this episode, I discuss 1,2-shifts that form ketenes and related reactions, including Wolff-rearrangement, the Arndt-Eistert reaction, Fritsch–Buttenberg–Wiechell rearrangement, and the Corey-Fuchs reaction.patreon.com/thatchemistCommunity Discord: discord.gg/QWNPETtPcZ ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:OG Wolff - doi.org/10.1002/jlac.190232502021st Wolff - doi.org/10.1016/j.steroids.2019.1085342nd Wolff - doi.org/10.1016/j.tet.2014.05.098OG Arndt-Eistert - doi.org/10.1002/cber.19350680142OG Fritsch-Buttenberg-Wiechell - doi.org/10.1002/jlac.18942790310Fritsch example - doi.org/10.1002/anie.200902760OG Corey-Fuchs - doi.org/10.1016/S0040-4039(01)94157-7mechanism paper - doi.org/10.1002/ejoc.200601137ynamine - doi.org/10.1021/ol017298ytrifluoropropyne - doi.org/10.1016/j.jfluchem.2022.109950cool example - doi.org/10.1021/ol035536e---------------------------------------------------------------------------------------------------------------------------
Hydroboration & Boron Rearrangements (IOC 44) That Chemist (old) 2022-05-07 | In this episode, I discuss 1,2-shifts of boron-containing motifs, including hydroboration/oxidation, the Matteson reaction, Zweifel olefination, and Aggarwal rearrangement.patreon.com/thatchemistCommunity Discord: discord.gg/QWNPETtPcZ ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:For the CDI/NaN3 example, here is a reference that accomplishes the transformation:doi.org/10.1021/jo00285a022hydroboration - doi.org/10.1021/ja01510a0591st boron oxidation - doi.org/10.1002/anie.2004601782nd boron oxidation - doi.org/10.1021/op20024971st phenol - doi.org/10.1002/bkcs.120122nd phenol - doi.org/10.1016/j.tetlet.2017.10.047Matteson reaction - doi.org/10.1021/ja00900a0171st Matteson example - doi.org/10.1021/ja00545a0452nd Matteson example - doi.org/10.1016/S0022-328X(00)00595-7Silyl-Matteson - doi.org/10.1021/om00074a006cis-alkene Zweifel - doi.org/10.1021/ja00990a061trans-alkene Zweifel - doi.org/10.1021/ja00773a059Aggarwal homologation - doi.org/10.1021/ja043632kAggarwal example - doi.org/10.1002/anie.201907617Evans paper - doi.org/10.1021/ja00257a041tertiary review - doi.orgAggarwal group website - http://www.chm.bris.ac.uk/org/aggarwal/publications.phpalkyl shift review - doi.org/10.1351/pac200678020215---------------------------------------------------------------------------------------------------------------------------
1,2 Shifts of Activated Amides (IOC 43) That Chemist (old) 2022-05-05 | In this episode, I discuss 1,2-shifts of activated amides, including Hofmann rearrangement, Curtius rearrangement, and Lossen rearrangement.Community Discord: discord.gg/QWNPETtPcZ ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:practice problem paper - doi.org/10.1021/ol103050cOG Hoffman - doi.org/10.1002/cber.188101402242OG Curtius - doi.org/10.1002/cber.189002302232OG Lossen - doi.org/10.1002/jlac.187216102191st Hofmann - doi.org/10.1002/jhet.55701807362nd Hofmann - doi.org/10.1002/ejoc.2015004661st Curtius - doi.org/10.1016/j.ejmech.2017.10.0252nd Curtius - doi.org/10.1002/anie.2020043211st Lossen - doi.org/10.1021/acs.oprd.0c003662nd Lossen - doi.org/10.1016/j.tetlet.2014.12.084---------------------------------------------------------------------------------------------------------------------------
Five Unexpected Reactions That Chemist (old) 2022-05-04 | In this video, I discuss five unexpected reactions that I observed during my PhD - chemical reactions often form unexpected products!Community Discord: discord.gg/QWNPETtPcZ0:00 Introduction0:09 Background0:30 Unexpected E21:47 Unexpected Cleavage3:07 Pure Chemicals Sometimes React4:17 Rings Like to Form5:24 Mercury is Promiscuous
Sulfur Ylides - Corey-Chaykovsky Reaction (IOC 42) That Chemist (old) 2022-05-03 | In this episode, I discuss sulfur ylides and the Corey-Chaykovsky reaction, which forms epoxides, aziridines, as well as cyclopropanes.On slide 8, I mistakenly say "the N parameters of ketones" but as aldehydes and ketones are electrophiles, I should have said "the E parameters".On slide 10, the oxygen is missing from the sulfonium after addition.Community Discord: discord.gg/QWNPETtPcZ ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:N-parameter database - https://www.cup.lmu.de/oc/mayr/reaktionsdatenbank2/ 1st thioether arylation - doi.org/10.1021/ol990069f2nd thioether arylation - doi.org/10.1246/bcsj.61.7073rd thioether arylation - doi.org/10.1039/P19830002913oxidation of sulfonium - doi.org/10.1248/cpb.c20-001321st epoxide - doi.org/10.1021/op30030852nd epoxide - doi.org/10.1016/j.ejmech.2017.10.063isoindazole - doi.org/10.1007/s10593-020-02699-0trifluoromethyl - doi.org/10.1039/C5CC04991A1st cyclopropanation - doi.org/10.1002/chem.2011016872nd cyclopropanation - doi.org/10.3390/molecules25040789chiral thioether catalysts - doi.org/10.1021/ar030045fTrost paper - doi.org/10.1021/ja00276a043Trost Ylide prep - doi.org/10.15227/orgsyn.054.00271st Trost -doi.org/10.1021/ol103050c2nd Trost - doi.org/10.1055/s-1998-16903rd Trost - doi.org/10.1021/ol101136a4th Trost - doi.org/10.1021/ol301331t---------------------------------------------------------------------------------------------------------------------------
An Overview of pKas (IOC 41) That Chemist (old) 2022-05-01 | In this episode, I give a primer into pKas, and discuss the best resources for finding pKas for various compounds.New Channel URL: youtube.com/channel/UC0nEDA3uRd5YuvBfMwQNteg/featuredIn the second practice problem, I mistakenly call the Leuckart reaction the Eschweiler Clarke reaction.Community Discord: discord.gg/QWNPETtPcZ ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:Collection of pKa data - organicchemistrydata.org/hansreich/resources/pkaEvans pKa table - http://ccc.chem.pitt.edu/wipf/MechOMs/evans_pKa_table.pdfBaran's book - books.apple.com/ca/book/the-portable-chemists-consultant/id618463142Baran heterocycle poster - https://www.scripps.edu/baran/heterocycles/Essentials1-2009.pdfN-parameter database - https://www.cup.lmu.de/oc/mayr/reaktionsdatenbank2/ ---------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Reductive Amination & Amide Synthesis (IOC 40) That Chemist (old) 2022-04-29 | In this episode, I comprehensively go through the main ways to accomplish reductive amination. The methods I discuss include NaBH3CN, Na(AcO)3BH, Pd/C & H2, as well as the Eschweiler-Clarke Reaction and the Leuckart Reaction. Finally, I discuss amide synthesis, as well as the synthesis of tertiary amines via iterated acylation and reduction with LAH.New Channel URL: youtube.com/channel/UC0nEDA3uRd5YuvBfMwQNteg/featuredCommunity Discord - discord.gg/QWNPETtPcZ ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:N-parameters - https://www.cup.lmu.de/oc/mayr/reaktionsdatenbank2/ first Borch - doi.org/10.1021/jm300917hsecond Borch - doi.org/10.1016/j.bioorg.2020.103824amalgam - doi.org/10.1021/ac9005588first Na(AcO)3BH - doi.org/10.1016/j.bmcl.2015.01.051second Na(AcO)3BH - doi.org/10.1248/cpb.c16-00610first Pd - doi.org/10.1016/S0960-894X(98)00246-7second Pd - doi.org/10.1016/j.bmcl.2006.02.008third Pd - doi.org/10.1016/j.bmcl.2014.07.020fourth Pd - doi.org/10.1002/anie.202002546fifth Pd - doi.org/10.1016/j.bmc.2008.07.062 first Pt - patents.google.com/patent/US20040192933second Pt - doi.org/10.1002/chir.20728 sixth Pd (Et3SiH) - doi.org/10.1021/acs.orglett.0c02156seventh Pd - doi.org/10.1002/EJOC.200500060first EC - doi.org/10.1016/S0022-328X(98)00686-Xsecond EC - doi.org/10.1002/ANGE.19951070916Leukart - doi.org/10.1021/ja01184a038first Leukart example - doi.org/10.15227/orgsyn.017.0076second Leukart example- doi.org/10.1021/jm9708083HATU example - doi.org/10.1021/jo071175vEDC example- doi.org/10.1016/j.tetlet.2013.09.136---------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Wittig & HWE Reactions - Alkene Synthesis (IOC 39) That Chemist (old) 2022-04-27 | I apologize that I pronounced 'Wittig' incorrectly in the introduction.In this episode, I discuss the Wittig & Horner-Wadsworth-Emmons reactions. These reactions are useful for the synthesis of alkenes. ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:first Wittig - doi.org/10.1016/j.tetlet.2011.01.076second Wittig - doi.org/10.1016/S0040-4039(03)01454-0third Wittig - doi.org/10.1021/ol802816kfourth Wittig - doi.org/10.1080/00397910500213054HWE using LiCl & DBU - doi.org/10.1016/S0040-4039(01)80205-7HWE review - doi.org/10.1055/a-1493-6331---------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Diazonium Substitution - Sandmeyer Reactions (IOC 38) That Chemist (old) 2022-04-26 | In this episode, I go through the various substitution of diazonium salts to nitriles, thiols, halides, sulfonyl chlorides, hydrogen, phenols, and boranes. Variants of this reaction include the Balz-Schiemann reaction, as well as the Rosenmund-von Braun reaction. ---------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:bromination - doi.org/10.1021/ol4023326iodination - doi.org/10.1039/C5OB00372Echlorination - doi.org/10.1002/cmdc.201000051fluorination - doi.org/10.1021/acs.chemmater.8b05327first xanthate - doi.org/10.1002/anie.201605597second xanthate - doi.org/10.1021/jo030212pfirst phenol - doi.org/10.1002/chem.200802722second phenol - doi.org/10.1021/jm401276hfirst nitrile - doi.org/10.1021/jm010244%2Bsecond nitrile - doi.org/10.1007/s00044-020-02676-4first reduction - doi.org/10.1002/anie.202012760antihistamine reduction - doi.org/10.1021/jm980462bborylation - doi.org/10.3184/174751918X15362432558247---------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Carbonyl Reductions - Mozingo, Wolff-Kischner & Clemmensen (IOC 37) That Chemist (old) 2022-04-23 | In this episode, I go through the reduction of carbonyls to CH2s using the Mozingo, Wolff-Kishner & Clemmensen reduction. I also go through the Corey-Seebach reaction.----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:first Mozingo reduction - doi.org/10.1021/ja9743194second Mozingo reduction - doi.org/10.1016/S0223-5234(99)80078-6first Wolff-Kischner reduction - doi.org/10.1016/j.tetlet.2013.11.080second Wolff-Kischner reduction - doi.org/10.1016/j.polymer.2013.06.018first Clemmensen reduction - doi.org/10.1021/jo00298a029second Clemmensen reduction - doi.org/10.1021/acs.orglett.9b02511----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
EAS (SEAr) Reactions - Nitration, Halogenation & Sulfonylation (IOC 36) That Chemist (old) 2022-04-22 | In this episode, I discuss the electrophilic aromatic substitution reactions (EAS; aka SEAr), particularly nitration, halogenation, and sulfonylation.If you already know about NMR, here is a pretty cool paper where they predict the site of reactivity (halogenation) on pharmaceutically relevant molecules based on their 1H & 13C NMR shifts:pubs.acs.org/doi/10.1021/acs.joc.6b00584----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:N-nitrosaccharin - doi.org/10.1038/s41467-019-11419-yN-nitrosuccinimide - doi.org/10.1002/chem.201902966bromination example - doi.org/10.1021/acsmedchemlett.8b00291iodination example - doi.org/10.1016/j.tetlet.2009.04.105original TMS-SO3Cl paper - doi.org/10.1002/jlac.198219820212first TMS-SO3Cl example - doi.org/10.3184/0308234041640762second TMS-SO3Cl example - doi.org/10.1021/jacs.5b07865third TMS-SO3Cl example - doi.org/10.1039/C7SC00430Cfirst HFIP nitration - doi.org/10.1038/s41467-019-11419-ysecond HFIP nitration - doi.org/10.1021/acs.orglett.8b01028HFIP halogenation - doi.org/10.1021/acs.joc.7b02920 HFIP thia-Friedel-Crafts - doi.org/10.1002/celc.201901212 ----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Friedel-Crafts & Relative Ring Reactivity (IOC 35) That Chemist (old) 2022-04-21 | In this episode, I discuss the Friedel-Crafts alkylation and acylation reaction, as well as introducing electron-donating and electron-withdrawing groups. I also discuss the use of a Friedel-Crafts alkylation as a method of synthesizing THC!----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:N-parameter database - https://www.cup.lmu.de/oc/mayr/reaktionsdatenbank2/Mayr's website - https://www.cup.uni-muenchen.de/oc/mayr/DBintro.htmlfirst Friedel-Crafts - doi.org/10.1002/adsc.201500288second Friedel-Crafts - doi.org/10.1007/s00044-019-02299-4Δ8-THC paper - doi.org/10.1021/acs.jnatprod.1c00567Δ9-THC paper - doi.org/10.1021/acs.orglett.9b00198original Δ9-THC paper - doi.org/10.1002/hlca.19690520427HFIP alkene - doi.org/10.1021/acscatal.0c00872 HFIP epoxide - doi.org/10.1016/j.chempr.2021.10.023 first HFIP acylation - doi.org/10.1021/acs.orglett.6b01460 second HFIP acylation - doi.org/10.1021/acs.orglett.5b02851Michael acceptor HFIP - doi.org/10.1039/C8RA01397G first cyclopropane HFIP - doi.org/10.1039/C8SC02126K second cyclopropane HFIP - doi.org/10.1021/acs.orglett.7b03688 ----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Special Topic - NaH Makes Solvents EXPLODE! (IOC 34) That Chemist (old) 2022-04-20 | In this episode, I go through the risks associated with using sodium hydride (NaH) in DMSO, DMF, and DMAc.----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:main paper - doi.org/10.1021/acs.oprd.9b002762500L pilot reaction - doi.org/10.1021/cen-v060n028.p004ARC paper - doi.org/10.1021/acs.oprd.0c00459----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Alkene Halogenation & Halohydrin Synthesis (IOC 33) That Chemist (old) 2022-04-19 | In this episode, I discuss the halogenation of alkenes using reagents such as bromine, NBS, and DBH. I also discuss the use of haloniums in conjunction with other nucleophiles, forming difunctionalized products! The formation of halohydrins is the most well-established example of this.----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:alkyne bromination - doi.org/10.1016/j.tetlet.2020.151786haloetherification - tinyurl.com/yckpj3j4halolactonization - doi.org/10.1039/CS9790800171haloazidation - doi.org/10.1021/ja01096a045first alkene halogenation - doi.org/10.1039/P29960002309second alkene halogenation - doi.org/10.1016/S0040-4039(00)99862-9first halohydrin - doi.org/10.1021/jm300353rsecond halohydrin - doi.org/10.1071/CH9901309----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Hydrogenation of Alkenes & Alkynes (IOC 32) That Chemist (old) 2022-04-19 | In this episode, I discuss the specific methods for selectively reducing alkenes, alkynes, as well as the general approaches for hydrogenation. I discuss P-2, Lindlar's catalyst, Stryker's Reagent, diimide, and other catalysts!----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:platinum hydrogenation - doi.org/10.1016/S0040-4020(01)82913-6palladium hydrogenation - doi.org/10.1021/ol061147jLindlar reduction - doi.org/10.1021/ol4024634P-2 reduction - doi.org/10.1002/jccs.200000004first metal reduction - doi.org/10.1021/jm0002533second metal reduction - doi.org/10.1021/ja005644ldiimide reduction - doi.org/10.1002/047084289X.rd235diimide reduction example - doi.org/10.1002/0471264180.or040.02Stryker reduction - doi.org/10.1021/ja00209a048Hantzsch reduction - doi.org/10.1002/047084289X.rn01318.pub2Stryker reduction example - doi.org/10.1021/ja00209a048----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Reaction Recap Exam Solutions (IOC 31) That Chemist (old) 2022-04-15 | In this episode, I show the solutions to the Exam from IOC 30!I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Reaction Recap & Exam (IOC 30) That Chemist (old) 2022-04-15 | In this episode, I recap the first 29 lecture of IOC, and I also provide some exam questions!I didn’t mention it in the video, but another method for amine synthesis is by the reduction of amides with LAH; since I haven’t formally discussed the synthesis of amides in this lecture series so far, I thought it would be unnecessary to mention.I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Baeyer-Villiger Oxidation of Ketones & Aldehydes (IOC 29) That Chemist (old) 2022-04-14 | In this episode, I discuss the Baeyer-Villiger Oxidation of ketones and aldehydes, typically affording esters as products.----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:first Baeyer-Villiger oxidation example - doi.org/10.1016/j.ejmech.2016.03.068second Baeyer-Villiger oxidation example - doi.org/10.1016/j.tet.2012.02.043third Baeyer-Villiger oxidation example - doi.org/10.1055/s-0037-1611563fourth Baeyer-Villiger oxidation example - doi.org/10.1016/j.tetlet.2020.152714fifth Baeyer-Villiger oxidation example - doi.org/10.1080/09168451.2014.962476sixth Baeyer-Villiger oxidation example - doi.org/10.1016/j.bmc.2009.09.047----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Upjohn Dihydroxylation & Cleavage of 1,2-Diols with NaIO4 (IOC 28) That Chemist (old) 2022-04-13 | In this episode, I discuss the dihydroxylation of alkenes (Upjohn Dihydroxylation) oxidative cleavage of 1,2-diols using NaIO4 (the Malaprade Reaction). When these two reactions are done together, it is known as Lemieux–Johnson oxidation.----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:Upjohn alkyne oxidation - doi.org/10.1021/cr60324a003OsO4 review - doi.org/10.1002/047084289X.ro007.pub3first Upjohn - doi.org/10.1021/ja908626ksecond Upjohn - doi.org/10.1055/s-0034-1378902NaIO4 review - doi.org/10.1002/047084289X.rs095.pub2first NaIO4 - patents.google.com/patent/WO2004005274A1/ensecond NaIO4 - doi.org/10.1080/15257770.2013.827793first Lemieux–Johnson oxidation - doi.org/10.3390/molecules26175349second Lemieux–Johnson oxidation - doi.org/10.1248/cpb.c16-00147----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Oxidative Cleavage of Alkenes & Alkynes - KMnO4 & Ozonolysis (IOC 27) That Chemist (old) 2022-04-12 | In this episode, I discuss the oxidative cleavage of alkenes and alkynes, using KMnO4 and ozone.Here is the video from ChemicalForce featuring liquid ozone:youtube.com/watch?v=vttsvMKQ1Yw*WARNING* ozone is very toxic, and ozonides can be explosive! Great care should be taken when you are working with them!!!----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:KMnO4 example - doi.org/10.1021/ja00859a006first O3 example - doi.org/10.1021/ja000293wsecond O3 example - doi.org/10.1016/S0040-4020(00)00912-1----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Epoxidation of Alkenes - DMDO, mCPBA, & NaOCl (IOC 26) That Chemist (old) 2022-04-11 | In this episode, I discuss the epoxidation of electron-rich and electron-poor olefins, using peracids, DMDO, hydrogen peroxide, and sodium hypochlorite (NaOCl).*Note: for some reason, I didn't manage to pronounce MMPP correctly; it's full name ismagnesium monoperoxyphthalate.*WARNING* peroxides can be explosive! Great care should be taken when you are working with them!!!----------------------------------------------------------------------------------------------------------------------------------Links to articles discussed in this episode:N-parameter database - https://www.cup.lmu.de/oc/mayr/reaktionsdatenbank2H2O2 - doi.org/10.1021/ol301068hNaOCl - doi.org/10.1016/S0040-4020(01)82010-XmCPBA - doi.org/10.3998/ark.5550190.0013.416peracetic acid - doi.org/10.1023/A:1015573902465first DMDO - doi.org/10.1021/jo00066a032second DMDO - patents.google.com/patent/WO2016090060A1/en----------------------------------------------------------------------------------------------------------------------------------I hope you enjoyed the video! I'm planning on making a full series of videos if these videos are helpful for people!Recommended Texts:J. Clayden, N. Greeves, S. Warren, Organic Chemistry Second Edition, Oxford University Press, 2012. (especially good for mechanism and physical chemistry explanations)T. W. G. Solomons, C. B. Fryle, S. A. Snyder, Organic Chemistry Twelfth Edition, Wiley-VCH Verlag GmbH & Co. KGaA, 2016.LibreTexts:chem.libretexts.org/Bookshelves/Organic_Chemistry
Just Another Naughty Nitration #Shorts That Chemist (old) 2021-05-19 | Hey, I'm a chemist in a research laboratory and I do science! I primarily do organic chemistry, especially with colorful compounds, mostly containing sulfur and fluorine. Carbon and hydrogen are my bread and butter, and I have made and isolated over 400 synthetic compounds (many novel, some known). I work with gases, solids, and liquids. I like to do crystalizations, distillations, and chromatography to purify my compounds. I am currently doing my PhD in organic chemistry.#Chemistry #Nitration #BadLabPractices
Bromination GONE WILD #Shorts That Chemist (old) 2021-05-19 | Hey, I'm a chemist in a research laboratory and I do science! I primarily do organic chemistry, especially with colorful compounds, mostly containing sulfur and fluorine. Carbon and hydrogen are my bread and butter, and I have made and isolated over 400 synthetic compounds (many novel, some known). I work with gases, solids, and liquids. I like to do crystalizations, distillations, and chromatography to purify my compounds. I am currently doing my PhD in organic chemistry.#Bromination #Chemistry #HydrogenBromide
Does a Sparkler burn in a Sealed Jar? #Shorts That Chemist (old) 2021-05-18 | Hey, I'm a chemist in a research laboratory and I do science! I primarily do organic chemistry, especially with colorful compounds, mostly containing sulfur and fluorine. Carbon and hydrogen are my bread and butter, and I have made and isolated over 400 synthetic compounds (many novel, some known). I work with gases, solids, and liquids. I like to do crystalizations, distillations, and chromatography to purify my compounds. I am currently doing my PhD in organic chemistry.#Sparkler #Chemistry #Fire
How Big Can An Experiment Get? 3 Liter Chemical Reaction! #Shorts That Chemist (old) 2021-05-10 | Hey, I'm a chemist in a research laboratory and I do science! I primarily do organic chemistry, especially with colorful compounds, mostly containing sulfur and fluorine. Carbon and hydrogen are my bread and butter, and I have made and isolated over 400 synthetic compounds (many novel, some known). I work with gases, solids, and liquids. I like to do crystallizations, distillations, and chromatography to purify my compounds. I am currently doing my PhD in organic chemistry.#Chemistry #Science #Reactor
Can You Separate Yellow from Blue? #Shorts That Chemist (old) 2021-05-04 | #Chemistry #Chromatography #Shorts
Fractional Distillation of Diglyme #Shorts That Chemist (old) 2021-05-04 | #Chemistry #Distillation #Vigreaux Column #Shorts #Science
Plasma Ball Illuminating Fluorescent Light Bulb #Shorts That Chemist (old) 2021-04-01 | This works with other fluorescent light bulbs as well#Science #Shorts #Plasma
Spectacular Red Emulsion #Shorts That Chemist (old) 2021-04-01 | #Shorts #Chemistry #Red #SeparatoryFunnel
Beautiful Crystals of a Pure Organic Compound #Shorts That Chemist (old) 2021-03-03 | #Chemistry #Science #Shorts #Crystals
Purple Smoke! Quenching Manganese Heptoxide #Shorts That Chemist (old) 2021-03-01 | #Chemistry #KMnO4 #Shorts #Smoke
Fire from Manganese Heptoxide plus Hexane - YES it is that reactive! #Shorts That Chemist (old) 2021-02-28 | #Chemistry #Fire #ShortsLet me know if you want me to do more Mn2O7 videos!
Crystallizing a Pure Oil - Yellow Chemistry #Shorts That Chemist (old) 2021-02-27 | #Yellow #Chemistry #Crystals #ShortsYou know what they say about yellow chemistry...
Decomposing NOBEL GASSES! Decarboxylation of Acids with Xenon Difluoride! #Shorts That Chemist (old) 2021-02-26 | #Chemistry #Xenon #HydrogenFluoride #Shorts
Fractionally Distilling Xylenes Using Science! #Shorts That Chemist (old) 2021-02-25 | #FractionalDistillation #Chemistry #ShortsCan you name the piece of glassware used for this distillation?
Fuming Nitric Acid is Dangerous and Gloves Wont Protect You #Shorts That Chemist (old) 2021-02-23 | #Shorts #Chemistry #Fire #NitricAcid
