OCHEM Complete StudyGuide
OCHEM Complete StudyGuide Organic Chemistry
Popular in Organic Chemistry
Popular in Organic Chemistry
This 93 page Study Guide was uploaded by MCATgirl on Wednesday December 3, 2014. The Study Guide belongs to Organic Chemistry at University of San Francisco taught by Organic Chemistry in 2014. Since its upload, it has received 153 views. For similar materials see Organic Chemistry in Organic Chemistry at University of San Francisco.
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Date Created: 12/03/14
l ll H E1 A W illli i fr Wu1 H H L Allkewe 3 aE39llIii39t1i 39iii rijga Alkyjie 5iI391iii lEEa HHE H H mnI11rnn1ia 4 1riT7n111y Sacmnd ry ill39mquotIzI a39 39lEL1 111rj1I1132 shmi e Imim 1l3 ramliie ame CI SiilIl ari1 3 ll quotlquoth lI 5 H Phosphate 7 FT H EL Fhl pli F r E 0 q Eff El ErT 3 Sin HIE H Ea H siiam imizdle H H cu sl lZ 1a1ridEr cl E12 pm if Hquot r739 if E3 llI5rpmllIlmritE m39lllZIillTitrE I llznurate delocalized electrons and resonance in ions and molecules 3 SulIl iIle A sllllige l3 5 5 x 5 5 5 FED Y f l I F PM E E 39 El e393 quotquot In r P 1 H l2 3939 Fern liIluH39aIIuE rigidity in molecular structure Multiple bonding increases rigidity in molecular structure 0 0 Single bonds can rotate but double and triple bonds can39t 0 Even partial double bonds like those found in the peptide bond prevents free rotation Stereochemistry of covalently bonded molecules isomers 0 Same molecular formula different structural formula 0 quotSame in writing different in drawingquot 0 structural isomers Strttcttirnl 5rI39ii m1Lt i E putrsitiutml 393quotquot39 on on N DH Eillll q HE EH3 cu 5 3 PO H 3ljquotquot t Elll quot tillHE H Eff rrgH3 39i39quotg 3 W k Aiquotquot3 H3Er J Ell3 ElH3 ItLi1 jgi lti1rl2l11 lirI1 Isofltut39fla1cohofl h LH3itili l 1t IttZiI l 1 t lnBiil ffI 391ttlt 3 l1 il E11111t1 ml i5ll lE Ei fhnttiman TH W3 7I3llg tZllg H2 fr cH2 tong titE Lll39jf1 Etltl hiiIi Eliiet hyl etlter Structural constitutional isomers have the same molecular formula but different connectivity Diastereomers have different physical properties Note in biological molecules people use D and L for R and 8 respectively Caution D and L absolute configurations are NOT the same as d and I relative configuration Read the section below on rotation of polarized of light for more details 0 conformational isomers Eclipfxsed Staggeresd K I quotsL39ifquots rquot quoti1 IIi1 rnlmi 2 CIii IZJT II E39Li391l3i7 lL1ItlI39 inLmi1l EH13 539waIerplmar E H EH3 mr5E n39H Sff f 3 bii39 39gy IH 39 3 3f39 j E39EPE Ei 39f39 Anti lowest torsional strain most stable bulky groups 180 staggered Single bonds will rotate such that it achieves the most stable conformation Conformers of cyclohexose Chair most stable everything is staggered Twist boat less stable things are not completely eclipsed Boat least stable everything is eclipsed Hexose rings will twist and turn to achieve the most stable conformation Torsional strain the strain due to eclipsing of groups across a single bond Steric interactions Axial most unstable because the axial groups are orientated with a high degree of clashing Equatorial most stable because the equatorial groups are orientated away from one another Bulky groups like to be in the equatorial position Most stable conformation completely staggered chair with bulky groups in the equatorial position Least stable conformation completely eclipsed boat with bulky groups in the axial position polarization of light specific rotation 0 Light is an electromagnetic wave Electromagnetic waves are waves of electric and magnetic fields in phase but perpendicular to each other and also to the direction of propagation Normal light has the EM fields in all directions in a 360 circle perpendicular to the direction of propagation Fiscllter itirujectimt H c oH H l tiH 0 T HE ciHro EH 355 s 39tftfH H EFl3 EH3 EH3 DH I r 2 i39quotflEl H33 cuts 0 Steps in assigning R and S refer to figure above 0 Absolute configuration is the R or S that39s labeled on the chiral centers a Is the carbon center chiral For our molecule the answer is yes because 4 different groups are attached to the carbon atom b Assign priorities according to the Cahn lngold Prelog rules see below c Turn the molecule such that the lowest priority group is at the back d Rotate from the 1st to 2nd to 3rd priority group like a steering wheel It39s R if you end up turning right and it39s 8 if you end up turning left note if you39re good at visualizing stuff you do this much faster by skipping step c 0 Relative configuration is always defined in relationship to another chiral center The direction that a molecule rotates plane polarized light is the prime example of relative configuration 0 Before the mid 1800s people did not have an understanding of the tetrahedral carbon atom so they did not have absolute configurations Instead they used the relative configurations of which way a compound rotates plane polarized light K i 1 IR SpeE wmtemmmttrEr15 em 3313 sewnI fawnI tiltI en Elii ae it 3 H Etititi 2t EQUU jw lii emit rr tttiti itiatiti ee i titi ee tgtiti e e l l ll r 1 r o intramolecular vibrations and rotations Vibrations bonds can stretch compress and bend like a spring It is this vibration that is measured in IRspec Primary colors of light 7 su Primary colors of pigments 6 Complementary color is the color that39s on the opposite side of the color wheel For example the complementary of red is cyan The absence of when you absorb a primary color of light you end up with its complementary color The primary colors of pigments is exactly the complementary colors of the primary colors of light This is because pigments absorb a certain color of light and reflect the rest back into your eyes Carotene absorbs blue light and reflect the others into your eyes The absence of blue produces yellow the complementary color of blue 0 effect of structural changes on absorption eg indicators Changes to chemical structure can lead to changes in absorption H indicator lt gt Ht Indicator H indicator absorbs at a certain wavelength and is of one color Indicator absorbs at a different wavelength so is of a different color At low pH high H H indicator and its color will predominate At high pH low H indicator and its color will predominate At neutral pH both H indicator and indicator will co exist in an equilibrium so the color will be a mixture of the two You should know the colors of the universal indicator Red very acidic Orange acidic Yellow weakly acidic Green neutral Blue basic Purple very basic ultraviolet region 0 pi eectron and non bonding electron transition Every time you have a bond the atoms in a bond have their atomic orbitals merged together to form molecular orbitals Every time you have molecular orbitals you get bonding molecular orbitals and non bonding andor anti bonding orbitals r quotSolvent llonpolar solvent quotWater Lonic and polar solutes dissolve ere Vonpolar solutes dissolve here lsolute he organic phase does not always float on ater is usually denser than other Density op Chloroform for example sinks below olvents but some organic he aqueous phase olvents are even denser Distillation Separates liquids based on boiling point The stuff with the lower boiling point is boiled off and collected the higher boiling point stuff remains behind o Simple distillation done with a normal column can separate two liquids if the difference in boiling point is large o Fractional distillation done with a fractionating column can separate two liquids with smaller differences in boiling point o Vacuum distillation done under lower pressure vacuum lowers the boiling point for all liquid components so you don39t have to crank up the temperature so high chemical might decompose Chromatography Basic Principles Involved in Separation Process 0 Those with greater affinity for the stationary phase comes out of the column slower Polar substrate has more affinity for polar stationary phase and hydrophobic substrate has more affinity for hydrophobic stationary phase Paper chromatography 0 Classically used to separate pigments in dyes o Solvent mobile phase Paper stationary phase 0 Pigments in dyes stick to paper solvent tries to wash them along those with greater affinity to paper stays behind those with greater affinity to solvent gets washed along 0 R value distance traveled by pigment distance of solvent front 0 R 0 means that pigment has not moved 0 R 1 means that pigment moved as far as the solvent front o Thin ayer chromatography 0 Thin layer chromatography advanced paper chromatography 0 Instead of paper you have a plate coated with a specific stationary phase of your choosing o R value used in the same way as paper chromatography Recrystalization Solvent Choice from Solubility Data o Recrystalization barely dissolving your compound then let it recrystalize out of solution compound ends up being more pure Barely dissolving use just enough to fully dissolve your compound under warm temperature saturated solution Recrystalize solution cools solubility decreases compound comes out of solution Solvent choice choose a solvent in which your compound is soluble in at warm temperature but not at cool temperature Also choose a solvent in which impurities are highly soluble o Impurities should remain dissolved in the solvent even when your compound recrystalizes out Aliphatic alkanes Description 0 nomenclature C atoms Name for straight chain alkane Name for cyclic alkane 1 Methane NA 2 Ethane NA 3 Propane Ityclopropane 4 quotButane ltyclobutane 5 Pentane ltyclopentane quot6 IHeXane Ityclohexane quot7 Heptane ltycloheptane quot8 Ipctane Ityclooctane quot9 Nonane Ityclononane quot10 Decane Ityclodecane After Decane there is Undecane 11 Dodecane 12 Tridecane 13 Tetradecane 14 and so forth for eleven membered alkanes upwards 0 physical properties Hydrophobic London Dispersion Forces present only Lower boiling points than compounds the same size but with functional groups Very long alkanes can have very high boiling points due to the sum of all the dispersion forces A useful reference is that heptane the 7 membered alkane has the same boiling point as water Important reactions o combustion Complete combustion of alkanes alkane or cycloalkane 02 gt CO2 H20 Complete combustion of anything fuel oxygen gt carbon dioxide water 0 substitution reactions with halogens etc Alkane halogen free radical initiator gt alkyl halide Free radical initiators hv UV light or peroxides Substitution occurs via a free radical mechanism see below General principles 0 stability of free radicals chain reaction mechanism inhibition The more substituted the radical the more stable it is Stability 3 gt 2 gt 1 gt methyl tita15 t stable Lcast sttlblc I l T T jig l39f Hjrj I I 3 2 1 it l39ll39 tE39tttquotiitt Substitution will occur preferentially at the more substituted carbon atom Cyclobutane has the second highest ring strain Cyclohexane has the lowest ring strain Any ring with greater or equal to 14 carbon atoms has the next lowest ring strain Stick with the above rule and you can answer any questions comparing ring strain The MCAT will not require you to make weird ring strain comparisions for example between cyclopropane and cycloheptane Ring strain consists of Angie Baeyer strain and Torsional strain Angle Baeyer strain is caused by deviation from the ideal sp3 tetrahedral bond angle of 1095 Torsional strain is caused by the molecule having eclipsed conformations instead of staggered ones Cyclopropane has both angle Baeyer strain and torsional strain Cyclohexane in the chair conformation has no angle Baeyer or torsional strain You39ll frequently see people write Bayer strain instead of Baeyer strain They mean the same thing 0 bicyclic molecules icyclic tttlecttles Fused E dgcd Bicyclic molecules have more ring strain than monocyclic molecules Except for spiro bicyclics which have similar ring strain as their monocyclic counterparts SN2 H r 39H2 Hit f H HI H gr lll H ii K NE a V 3939 Hri WEH itmu E A H H Hf E iii f ll t39Ii311 1Ull 1 state F NH H H 39 HEB 0 Factors that favor sn1 stable carbocation tertiary carbon center protic solvent 0 Factors that favor sn2 unstable carbocation primary carbon center aprotic but polar solvent 0 All substitution reactions need a good leaving group 0 SN1 unimolecular reaction intermediate carbocation formed 0 SN2 bimolecular reaction passes through transition state oxidation 0 KMnO4 and CrO3 will oxidize primary alcohols to carboxylic acids but PCC Pyridine Chlorochromate and other weak oxidizing agents will only oxidize a primary alcohol to the aldehyde 0 Secondary alcohols always oxidize to the ketone o Tertiary alcohols do not oxidize lll x m l Em C C A J 1 T tj A t H r i H gr an 3 Q Q I I 1QEi lli2 on ll an E1 lll is P p P 131 5 l391 t1 fl lttf 11111 lll ill an toajgiaitc on l a H3lZ2 39 1Ci lllliZJ R i H33 5 3 Ft ll J ll 3 39ifl1 Cl 39339 111111t1ll iltei yl t Sulfonates RS03 are good leaving groups The R can be Methane which makes methanesulfonate Toluene which makes tosylate Trifluoromethane which makes triflate Mesylates can be prepared by reacting an alcohol ROH with mesyl chloride MsCl Tosylates can be prepared by reacting an alcohol R OH with tosyl chloride TsCl Reactions involving the formation of inorganic esters F 13 3 Rtttt n H3P39rtCi3 ER HI A as RmwPt iiIlir r H zlaquotE It39llquot F not H emf H E 1 DH H39 p Haiti 39rF a H to ET 3 Raf 139 a H r on F 4 H R 1 H SE13 EH 3 SE32 5 i211131 5 R i p iIl i tillm E s p 1 H ER W En o quotquot 39quot39 l S 1 RC ti Formation of mesylates and tosylates are also reactions that involve inorganic esters HQ ii A I t H E 39 4H Ii1L1I ilLL i3i1 hti1E attacis mt tits Triimitt Lttt1at1t torLiatt tc ir catiiaattj quot o oc3 unsaturated carbonyl nucleophile gt addition of the nucleophile at the 3 position 0 Nucleophile attacks the beta hydrogen pushing the oc3 unsaturated carbonyl into the enol form which tautomerizes to the original carbonyl Old AAMC topics acetoacetic ester syntheses this topic has been moved to the keto acids and esters section 2 x ethylacetate gt ethyl acetoacetate acetoacetic ester 3 keto ester Claisen condensation 1 alpha proton of ester leaves 2 the resulting carbanion attacks the carbonyl group of another ester molecule 3 Carbonyl group reforms and kicks off the alcohol group 0 quotAcetoacetic ester synthesisquot is a reaction where acetoacetic ester is used to synthesize a new ketone Acidic alpha proton comes off resulting carbanion attacks new R group Hydrolysis of ester turns it into a 3 keto carboxylic acid 3 keto acids undergo decarboxylation because the 3 keto group stabilizes the resulting carbanion via enol formation Enol converts back to keto form and the net result of this reaction is that an R group is made to attach to the or carbon of acetone Description o nomenclature o Suffix oic acid carboxylic acid dioic acid physical properties and solubility 0 High boiling point due to hydrogen bonding o Soluble in water infrared absorption 0 CO at 1700 cmquot 0 OH at 3100 cmquot Important reactions carboxyl group reactions 0 nucleophilic attack Iquotttc1atptt1it attaclt mt EDIDH r J E I7ttc1aaptt1iat attac a ay Cili H Ci Ci I39t5 ILii Q Q 9u t u Q m q 339 M E Rh mic Rt E1 l ID ff tx l lItE O Nucleophilic attack occurs on the electrophilic carbon of CO Nucleophilic attack occurs by the nucleophilic oxygen of COOH 0 reduction LiAH4 COOH gt alcohol 0 decarboxylation occurs for betaketo acids E o O o esterification COOH ROH under acidic conditions ester Halugm1atlil1 ti C 1I39lili quot il39liE Acids a1 lll1se u position 11 39EIai1i iIr39iEH tutu Ei1IlIIiE IE Farm E E H 1 quot 13quot H H3 H2 Earbotg lic tt il l mcyl lt1aIli lc Ph E 1lTIiIE IEIH o HF Emix Em V H2 H I39l tllIligE l i ll fl Tl Rf Cfquot F H H E IF Her r 4 Hetrert hack to ltatlmu3t3sl acid a39 1 V HE quot39Aquot quot39 5 c on 3 Br 3 l K J l Ear i fdr lly wig Q EH r r o substitution reactions RCOOH Et gt substitution at the alpha carbon 2 position Carboxylic acid converted to Acyl Halide which can enolize Acyl Halide tautomerizes to its enol form by abstraction of acidic alpha hydrogen Halogen or some other Et gets attacked by alpha position Revert back to carboxylic acid The net effect is that the alpha H get substituted by an electrophile o Amides have higher boiling points than the other acid derivatives 0 Acid derivatives have high boiling points than alkanes because of the CO dipole interactions infrared absorption 0 Acid chloride the CO will show up at greater than 1700 cmquot pretty close to 1800 cmquot 0 Anhydride the double CO doesn39t show up as a single band Instead 2 bands shows up between 1700 cmquotand 1800 cmquot 0 Amide the N H shows up around 3300 cmquot the CO shows up at 1700 cmquot 0 Ester CO group shows up at 1700 cmquot The C0 ether stretch shows up around 1200 cm Important reactions preparation of acid derivatives 0 Carboxylic acid SOCI2 gt Acid chloride 0 Carboxylic acid carboxylic acid heat gt Anhydride 0 Acid chloride carboxylic acid base gt Anhydride 0 Acid chloride alcohol base gt Ester 0 Acid chloride amine gt Amide 0 Acid chloride water gt Carboxylic acid Hofmann rearrangement Hofmann rearrangement takes away the CO of an amide The alkyl migration is basically how the R group on the other side of the CO migrates and attaches itself to the nitrogen atom See figure below for detailed mechanism of the Hofmann degradation and how the aryl group migrates l39II i quotl I 1 39tIi1Ii1 lcgratltttion ot tttitlcs Elli T DH Hf mi 3 HHE Hf RHH2 ilarflgrtttioutt of tits t1lltjr il grottjii ilIllt1ul i1tiiitquotlrt n1cclt1aniaIt1 D 3 Cl l ll l Hr HH2 HHE a H if H rtc Ijrt Cl 39 Di 39 1 flag 9 ll H i i H t M x3t e H Eli 39h lZ339A391Ii1fi l39IquotCiflli2 Cl H Kg u 5 C H A Alltyl IlIlligE39EIl39i39I139Ill ri i quotstc1 l tt1i trrna quot35 E37iilliiiAl 3 0 A 0 A H H2 Hofq anf HEHM H a transesterification Ester alcohol gt new ester ti R H Pk T t f TAT it 39391H EQH General principles relative reactivity of acid derivatives Acid chloride gt Anhydride gt Esters gt Amides 0 Acid halides are the most reactive derivatives because halides are very good leaving groups 0 Amides are the most stable derivatives because NR2 is a terrible leaving group Also the C N bond has a partial double bond characteristic Proteins are made of peptide bonds and they are very stable steric effects bulky groups around the CO group helps protect the carbon center from nucleophilic attack electronic effects groups that can redistribute and stabilize negative charges are good leaving groups For example the anhydride has a good leaving group the carboxylate ion because the CO0 can redistribute the negative charge to both oxygens via resonance strain eg beta lactams o Amides have a double bond characteristic between the carbon and nitrogen This means that the C N bond can not rotate 0 Normally the sigma bonds in a ring rotate as to achieve the most stable conformation but this can39t occur for the C N bond if the ring contains an amide 0 Because C N bond in an amide can not rotate rings that contain amides have higher strain 0 An example of this is the beta lactam which is basically a 4 membered ring with 1 amide in it Description nomenclature o betaketo esters gt betaketo acids gt enols gt ketos o decarboxylation of beta keto acids is facile because the enol stabalizes the reaction intermediate acetoacetic ester synthesis Eymthesizing t cetnacettc Ester Ace truaaceetijc Esttei Cr iIlEEiE IS Iiii1tlI ethyl EIJEEIEDE EZilEt391 JtE11l39EIli1 nut artIiiw prrstitmt by harse iii a EH Ci ll I quotquotquot H B H3IEIE2zEiEt H2t3 i riEt H2EI39l1tZiEt if Ci ti Ci H3Il73 IE2tCiEt H3c c c r riEt aieIitaiaEEIiaE ester 3939aEEfEquot i2IE39iIiIi2 Ester Ej39T th E5aiS Lisijimg a39iEE t 39EEtiE E39 iZE i tn 1 ji39t1 l39I1ES iEEI Ci Ci 39339 0O H2 0 5 C H313 E E E DEE H31 393 EIEEEHEEJIEETUE FEEiEI39 i DEE Ilj GI 39iig5lair iquotquotE quotl i9 7 quot E DtcarIt1at3lt1t ittn c riH 12 H3cJ c cHE ED p I39739II EtneE E EHIIIFEI Usually the acide derivative is acyl chloride with chlorine as the leaving group However any other good leaving group will work An important biological amide formation is the peptide bond formation in protein synthesis Here amine carboxylic acid gt amide The leaving group is water not OH 0 reactions with nitrous acid 39 Ar39NH2 Ar N2 H20 P nitrous acid HNO2 HONO 1 a The reason why the nitrogen in nitrous acid can be attacked is the following o stabilization of adjacent carbonium ions carbocations TLT if H fiII2 p qi IIE The nitrogen of the amine donates its lone electron pair to the adjacent carbonium ion carbocation 0 effect of substituents on basicity of aromatic amines 39r IE39E39 llm Still Less lime Less Ilil itt r39Ill1t efquotllquot39ett o xg Equot 15quot39iITlll39iquot5153939ii1iI gruttp Erquot iaimiliit1g grmip Aromatic amines are weaker bases than aliphatic amines This is because the amine donates its electron density to the aromatic ring Also the amine forms stable resonance structures with the aromatic ring which is absent once the amine becomes protonated Electron donating groups on the aromatic amine increase the basicity of aromatic amines This is because the electron donating groups contribute to the electron density on the nitrogen Electron withdrawing groups on the aromatic amine decrease the basicity of aromatic amines This is because the electron withdrawing groups steal electron density from the nitrogen Anything ortho to the amine no matter whether it is electron donating or withdrawing will decrease the basicity of the aromatic amine This is because of the ortho effect which is basically sterics OH groups that are pointing Right on the Fischer becomes Down on the Haworth The OH group on the anomeric carbon the Fischer carbonyl can be either up beta or down alpha The CHZOH group on the absolute configuration carbon carbon 5 points up for D and down for L LEHHT Stttlzllllt Flmmr W nt lirn iIn39gj II391 lquot l quotl39tt139it39 Iiilitll Twiiill zHJ39E T Equot quot1LEIEiI Elfablre 1quot I12 39 m Li l at Equot5l39ll l39Tl39gf In the planar conformation everything is eclipsed In the chair conformation everything is staggered All the conformations in between are partially eclipsed The Boat conformation has Flagpole interactions because axial groups attached to the head and tail of the boat clash The Twist boat conformation lessens these Flagpole interactions in addition to reducing the number of eclipsed interactions epimers and anomers Eimarttiomers EliEEl EH HEIDIl O Hydrolysis of the glycoside linkage Glycoside linkage acetal linkage linkage involving the hydroxyl group of the anomeric carbon Glycoside linkage can also mean the linkage between the sugar and the base in nucleotides Examples of glycosidic linkages starch glycogen nucleotide Hydrolysis of the glycosidic bond has the same mechanism as hydrolysis of the acetal bond glycoside H20 catalyst gt hydrolysis Catalysts include Amylase for starch and glycosylase for nucleotide Reactions of Monosaccharides both the aldehyde and the terminal hydroxyl to carboxylic acids but leaves the other hydroxyls alone Reduction turns monosaccharides into polyalcohols Description absolute configuration at the alpha position BID ll iiitii ll HEN H H H HE R H L I1t1 i r39ii tciifl quot539L t1iItiii Acitl o L and D is different from R and S L is not always 8 and D is not always R o If the priority of NH2 gt COOH gt R then LS and DR For example L Alanine S Alanine o If the priority of NH2 gt R gt COOH then LR and DS For example L Cysteine R Cysteine o Lamino acids are the more common in nature and are the type found in proteins D amino acids are less common in nature and are never found in proteins amino acids as dipolar ions classification In E39te39 E ftEufr n 0 At low pH amino acids exist in the cationic form 0 At high pH amino acids exist in the anionic form o The peptide bond is formed by the amine group attacking the carbonyl carbon o hydrolysis El DH 0 The peptide bond is very difficult to hydrolyze It requires a strong base or a biological enzyme General principles primary structure of proteins 0 Primary structure sequence 0 The primary structure of proteins is read from the N terminus to the C terminus secondary structure of proteins 0 Secondary structure repetitive motifs formed by backbone interactions 0 Backbone interactions hydrogen bonding between the NH and CO o The two most common secondary structures are or helices and 3 pleated sheets 0 The or helix is right handed with the R groups sticking outward o In 3 sheets R groups stick out above and below the sheet l 5ouprcnc A one V L s539srtitratclll o1ttf1 ot 3iJpt t391E SF Lt11l39tE139gt n391g pt11t1nErizu tit1t Tcrjiicttc li3391ilE lZit11ut39iI ioat Tarwcnc Terpenes are made from the polymerization of isoprene Terpenes contain double bonds which gives the molecule the ability to undergo cyclization Squalene the precursor of steroids is a terpene that consists of 6 isoprene subunits A complex selfcyclization reaction converts squalene to make steroids Squalene is classified as a triterpene Triterpene 6 isoprene subunits Diterpene 4 units Monoterpene 2 units triacyl glycerols O O Wiitt g Reactinn E 317 Ph3FG jinn 32 iJIFquotFquoth3 I11Enhani39am U Pph E quotPPh3 p p El y E Jr NR 39 IIrr3 1 mg ppra PPIh D PPh3 I 3 H 1 quot3 1quotquot FL 3quot 3 Carbonyl Phosphorus Ylide gt Alkene The C1O Ph3PC2 397 C1C2 Most Wittig reactions are not stereospecific
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