123.312 Advanced Organic Chemistry: Retrosynthesis
wedby reduction.NH2FGINHOC NreductionNH2FGIN3C–NOTsOHC–SreductionQuestion 4.Perform the retrosynthetic analysis of the following compound. Remember, your planned synthesismust be synthetically possible and shouldn’t suffer from regio- or chemoselectivity issues.OONEt2ONH2Answer
OOONEt2OHOFGIC–OONH2OOHFGIN2 BF4–ONH2NO2the amine can be problematicso we convert it to the lessreactive nitro group. This alsoprepares the way for itseventual disconnectionOC–OOOHwe can now remove the ether.Attepts to do this earlierwould have met with failuredue to alkylation of the amineOHC–NdiazoniumFGIdiazoniumOreductionOremove the ester(with the reactivefunctionality)OHNO2I would stop here as I don't know how mucharomatic chemistry you have done. But if youhave done enough then we can take thesynthesis all the way back to the acidOHOOHFGINH2OHOHOthe phenol group is ortho, paradirecting but should favour theleaser hindered position (andwe might be able to argueabout H-bonding)OHC–NreductionNO2remember, the acid is electronwithdrawing so is meta directingQuestion 5.(a)How would you synthesiseFromAnswer:i. BH3ii. H2O2 /NaOHPBr3OHBrRemember, we need to get anti-Markovnikof addition of the hydroxyl group so we use hydroboration /oxidation.
(b)How would you synthesiseOHFromAnswer:Br2,hvBrt-BuOKi. BH3ii. H2O2 /NaOHOHThe key to this one is functionalisation of the hydrocarbon. This is achieved by radical bromination,then its plain sailing.(c)How would you synthesiseOHFromBrAnswer:BrMgEt2OMgBrCH3CHOLets be honest, if you can’t do this one then you’re in trouble!(d)How would you synthesiseHOFromOH
HOAnswer:EtMgBrPCCOHOHOLikewise, this one is not that taxing but hopefully gets you thinking about functional groupinterconversions.(e)How would you s one is quite hard. But again, it is all about FGI and recognising where the original carbons are. Irecommend number you carbons and then trying to identify relationships between functional groupsand this numbering.(f)How would you r
Quick, but not necessarily straightforward; the more reactions you know the easier this becomes. Herewe require anti-Markovnikov addition of the HBr. Therefore, we add peroxide to allow a radicalreaction.(g)How would you synthesiseNH2OFromOAnswer:HBrROOROBrOPPh3H 2ON3NaN3ONH2OAgain, need anti-Markovnikov so use radical bromination. The add nitrogen via the azide. Of course,there are other answers (hydroboration , oxidation and reductive amination?)(h)How would you synthesiseNHPhFromOOEtAnswer:OH3O OEtOOOHSOCl2PhNH2ClHopefully, this one doesn’t cause too many problems.(i)How would you synthesiseONHPhLiAlH4NHPh
OHEtEtFromEtO2CCO2EtAnswer:EtO2CCO2Eti. baseii. Et–IEtO2CCO2Eti. baseii. Et–IEtO2CCO2Eti. H3O ii. heatEt EtEtEtCO2HLiAlH4EtOHEtEtThis one is all about recognising which functional groups are required and how they can beinterconverted.(j)How would you synthesiseOHOHFromOAnswer:i. baseii. EtCHOOOOHNaBH4OHOHDon’t get fooled by how similar molecules may appear. Count the atoms, look for real relationships.In this case we have a 1,3-diol derived from a ketone; start thinking about an aldol reaction right away.(k)How would you synthesiseBrFrom
OHAnswer:OHPCCOMeMgBrOHacidHBrROORBr
The next isnÕt much harderÉw e have an alcohol, this should yell Grignard addition to a carbonyl and hence the disconnections are: OH O CÐC BrMg Br . In this case we have a 1,3-diol derived from a ketone; start thinking about an aldol reaction right away. (k) How would you synthesise Br From . OH Answer: OH PCC O MeMgBr OH
Chemistry ORU CH 210 Organic Chemistry I CHE 211 1,3 Chemistry OSU-OKC CH 210 Organic Chemistry I CHEM 2055 1,3,5 Chemistry OU CH 210 Organic Chemistry I CHEM 3064 1 Chemistry RCC CH 210 Organic Chemistry I CHEM 2115 1,3,5 Chemistry RSC CH 210 Organic Chemistry I CHEM 2103 1,3 Chemistry RSC CH 210 Organic Chemistry I CHEM 2112 1,3
123.1 3 RESCO (Ohio) Patronage 123.16 WPSC - Power Supply Development Fund 123.40 Wolverine Power Supply - Membership 123.42 NRUCFC -Membership 123.43 MECA - Membership 123.45 NRTC - Membership 123.64 MECA - Building 123,21822 NRUCFC - Capital Term Certificates 123.00 RESCO -Stock 123.1 5 NRTC 123.01 RESCO -Class 0 Stock
Textbook Essentials of Organic Chemistry by Dewick The following textbooks are also available in the chemistry library on reserve: Organic Chemistry: A Short Course by Hart, Craine, Hart and Hadid Introduction to Organic Chemistry by Brown and Poon Fundamentals of Organic Chemistry by McMurry Essential Organic Chemistry by Bru
In Press Advanced Inorganic Chemistry Gurdeep Raj 06 270 Chromatography B.K. Sharma 06 Organic Chemistry 302 Advanced Organic Chemistry Aditi Singhal 08 279 Organic Chemistry Natural Products - Vol. I O. P. Agarwal 09 280 Organic Chemistry Natural Products - Vol. II O. P. Agarwal 09 281 Organic Chemistry Reactions & Reagents O. P. Agarwal 10
E11047 27, 32, 35 E11196 123 E11197 123 E11199 123 E11200 123 E11214 126 E11219 126 E11220 128 E11221 128 E11223 128 E11224 128 E11231 124 E11232 124 E11382 CRUUS 125 E11384 CRUUS 125 E11446 CRUUS 126 E11450 CRUUS 126 E11486 CRUUS 123 E11487 CRUUS 123 E11492 CRUUS 123 E11493 CRUUS 123 E114
Saxophone Trill Chart A3– B3 A 123 Bb 123 C Trill the low A key. For models with a low A key. A3– B3 A 123 B 123 C Trill the low A key. For models with a low A key. 123 B Bb 123 C Impractical. A3– B3 B3– C4 123 Bb 123 C Finger A# 3. Extend RH 2 across bell stack to hold low B closed, pressing directly on the pad cup arm with the top .
Advanced Organic Chemistry, Part B, 4th ed. F.A. Carey and R.J. Sundberg ISBN: 0-306-46245-1 The Art of Writing Reasonable Organic Reaction Mechanisms R.B. Grossman Writing Reaction Mechanisms in Organic Chemistry A. Miller ISBN: 0-12-496711-6 Advanced Organic Chemistry, J. March, 4th or 5th edition ISBN: 0-471-58589-0
CHEM 0350 Organic Chemistry 1 CHEM 0360 Organic Chemistry 1 CHEM 0500 Inorganic Chemistry 1 CHEM 1140 Physical Chemistry: Quantum Chemistry 1 1 . Chemistry at Brown equivalent or greater in scope and scale to work the studen
