Organic Chemistry: Naming Compounds, Oxidation States, and Reactions, Exams of Sociology

Download Organic Chemistry: Naming Compounds, Oxidation States, and Reactions and more Exams Sociology in PDF only on Docsity! Sociology Final Exam Questions with Verified Answers 2024 Test Perfectly Answered Chapter 1: Nomenclature - Correct Answers Naming or go camps - Correct Answers 1: ID the longest C chain with the highest priority functional group (most oxidized C), this is suffix 2: Number the C chain with C1 being the C next/closest to the highest priority Fig, if both Fig are the same (alkyl alkyl) then number it based on the one closest to the most terminal -Rings: start # at highest C attached to Fig and end with lowest Fig -If tie btw double bond and triple, double bond has priority -end before -yen) 3: Name the substituents, this is your prefix (broom), if multiple use di, tri etc 4: Assign Numbers to subs based on which C attached to and add di, tri etc 5: Add everything together in alpha order, ignore district, tart etc but is, neo, or cycle etc are included and use based off the first letter etc Oxidation States/figuring out highest priority Fig - Correct Answers Oxidation State increases with more bonds to heteroatoms or those that are not C, H, N, O, and PO4n Decrease with more bonds to H T-butyl - Correct Answers Form a small t Neopentyl - Correct Answers isopropyl - Correct Answers propyl (3C) iso means equal, these guys are symmetrical iso-butyl - Correct Answers butyl (4c) iso means equal and these guys are symmetrical if laid out flat sec-butyl - Correct Answers butyl (4c) sec bc extra C on second carbon vinyl - Correct Answers Naming Alkenes and Alkynes - Correct Answers -end =alkenes (double bond) -yens=alkynes (triple bond) -if multiple double bonds __end or #-X-dyne -Remember name is based on highest Fig; if other Fig on it that is higher this is just part of the whole not the suffix (substituent) -do NOT need to put Cs it’s in btw, can just put the first/lowest number (btw 5-6 then 5- ene) Naming alcohols - Correct Answers -suffix of ___old, numbered with lowest C/most terminal being attached to it, even if multiple bonds present (doubles are subs) -old over end bc OH is more oxidized, but note that it'll be #-en-#-old -if alcohol not highest Fig, then is a prefix of hydroxyl_________ -if multiple then suffix of ____idol, be sure to # each OH group Alcohol to ester - Correct Answers A current alcohol can be removed by an AL oxide ion (CH3O-) and essentially swap out the old OH to OR -CH3-X +SB -> H-OR Ex: CH3Cl +Noah -> H-OCH3 or OCH3-, -think about it the Na and OH easily disassociate, that means left with OH-, w/ OH- it then is stronger nun (bc nag) so can kick off the Cal (SA CB are good L groups) which creates OH-R -if reactants on top of arrow don’t make sense in what they clearly will do to the reactant in left of arrow then see how they can react to attack the reactant ethyl alcohol - Correct Answers ethanol ethyl (2C) Isopropyl alcohol - Correct Answers secondary OH germinal dials - Correct Answers -dials with hydroxyl groups on the same carbon -also called hydrates, uncommon bc they spent. dehydrate to carbonyls -germinal: attached to same group -overall: n-______-parent chain amide -suffix amide -if not highest priority then carbonyl- Naming Anhydrides - Correct Answers -to form these H20 is taken out from two CA -most are cyclic bc of intermolecular dehydration of a carboxylic acid -end in _____anhydride based off the CA that formed it, if two diff ones formed it then use the names of CA used in alpha order -an=without + hydride=water Functional Groups in order - Correct Answers Groups in order: CA> anhydride> ester> amide> aldehyde>ketone >alcohol>alkene>alkyne> alkane Chapter 2: Isomers - Correct Answers ALL ISOMERS HAVE THE SAME FUNCTIONAL GROUPS BUT differ in connectivity (constitutional) or in confirmation (conformational isomers) -when thinking of isomerism think of comparing two compounds not one single compound, so an antimere is an enantiomer to another mole it can’t just be one itself (nothing to compare it to) -Isomers are different compounds that have the same molecular formula. chiral center - Correct Answers carbon with four different substituents and lack a plane of symmetry -A property of a compound to exist in both left and right forms; occurs whenever a compound contains an asymmetric carbon constitutional isomers - Correct Answers -also called structural isomers; they have the same formula just different connectivity -have DIFFERENT chemical and physical properties only share formula -achiral (not optically active) physical v chemical properties - Correct Answers -physical properties: no change in the composition of matter, like melting point, boiling point, solubility, odor, color, density, also connectivity -chemical properties: the reactivity of a molecule resulting in change in composition bc of the functional groups attached to it Melting Point and BP - Correct Answers -bop: More H bonding higher -MP more covalent bond higher (more E needed to break away bond) -Bop/MP usually together freezing point is the pop of MP stereoisomers - Correct Answers Same connectivity just differ in how the groups are attached in space (in front or below etc) -stereoisomers all have same connectivity but can be broken down into configurationally (rate bond) or conformational (diasteromer etc) -For aim purposes; when asked how many of these, they are asking for the #chiral centers (only Cs) wt 4 subs then 2^# -basically asks for the number of Cs that are stereoisomers so exclude N, Os etc Stereo centers in org mole - Correct Answers Keep in mind that the Hz is never depicted in rug mole -also keep in bind stereo center needs 4diff figs, even if it doesn’t have the forward or back it still can be a stereo center (even if 3 figs are planar) just need to meet 4fg criteria (note in pic S toward was planar to confuse u in passages) Stereo center v Chiral Center - Correct Answers -Stereo center: any point that can form a stereoisomer (same connectivity diff position of ff in space) BUT they do not need to be all single bonds, they can be double bonds (includes geo isomers) -Chiral Center: 4 diff functional groups with single bonds around a C, it is a stereo center for a C mole -Stereoisomers: are spatial isomers either conformational (just needs rotation) or configurationally (orientation in space, R/S/geo etc) -Configurationally Stereoisomers: can be divided into optical (R/S-entity/die) or geo (cist/trans or e/z w/ no stereo centers aka 4fg around a C in single bonds) -If a mole is planar and asks for stereoisomers then u can’t assume forward in back and just count things (FOR STEREOISOMERS) NEED to use the 2^x formula since u have no idea on their orientation, stereoisomers is not the same has stereo centers! -geo isomers can then be: cist v trans (if two main ff) or E/Z if using toward/away or 2 or more ff (an EZ can name a cist/trans though but better suited/more universal and better for orientations of R/S in die) irk about the toward/away part though I think that only applies when double bond present bc double bond wouldn’t let u get R/S but the e/z would help u get the Fig in understanding), -Geo isomers=diastereomer bc each C is a sterocenter Conformational Isomer - Correct Answers not the same thing as R/S, R/S are stereo center. Conformational isomers can have stereoisomers on its end but isomerize does not work to rate the bond bc isomerize breaks and forms bonds Conformational isomers v configurationally isomers - Correct Answers -Conformational Isomers differ at the rotation of a single sigma bond (straight chains, think of rotation of circles of Fischer)-achiral -configurationally isomers: can only change if you break bonds - CAN BE chiral or achiral (mesocmpds, R/S etc) both are stereoisomers. think of conformational as conform at one point and configuration as R or S configuration Stereoisomer: same connectivity just diff oreitniation stereospecific reaction - Correct Answers -rxns in which the isomeric recants each provide a certain isomeric PRODUCT -ex: SN2 inverts configuration so that stereospecific, think R reactant gives S product and S reactant gives R product -When thinking stereospecific think that the product made is ONLY one stereoisomer not racemic (only cist or only R etc) -Does not need a specific configuration to run just gives certain stereo product conformational isomers - Correct Answers Stereoisomers that differ by rotation about one or more single bonds, usually represented using Newman projections. -seen bc the sigma bond is free to rotate Straight-chain conformations - Correct Answers - in a Newman projection the biggest groups will be anti to each other and here there is a minimal steric repulsion btw e- clouds, torsional strain -anti (180º)>gauche (60º)>eclipsed (120º)>totally eclipsed (0º) -angle is angle btw the 2 biggest groups -Racemic: 0 (be +/- cancel out) https://www.reddit.com/r/Mcat/comments/6f8qu0/ what_is_the_difference_between_rs_absolute/ Absolute Configuration V Relative - Correct Answers Relative configuration: The position of atoms or groups in space in relation to (i.e., relative to) something else in the molecule. Compare with absolute configuration, which is independent of atoms or groups elsewhere in the molecule Seperating Racemic Mixtures - Correct Answers -bc enantiomers have the same chemical and phsyical properties then only way to seperate them is through their run by turning them into diasteromers -reacting 2 enationmers (same chemical properties) with a single known enationmer to produce a diastereomer (diff chemical physical properties) Ex: have a +/- then react it with a known + to make +,+ and -,+ then you can filter the diasteromer out through physical properties like crystalization, filtration, distillation, etc (bc diast. have diff chemical and physical props) Diastereomers - Correct Answers -stereoisomers that are not mirror images of each other -occur when mole has multiple chiral centers (2 or more) and have different configurations at some BUT NOT ALL sterocenters -2^n (N=chiral centers) gives u amount of possible stereoisomers -they have DIFFERENT CHEMICAL PROPERTIES and PHYSICAL PROP -bc they have the exact same Fig but differ in their confiration then they have the same IR frequencies BUT have "shifty bands" not well behaved so found in fingerprint (can tell differnece in diasteromer via diff in finger print) Types of Diastereomers - Correct Answers Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more (but not all or else entatiomer) of the equivalent (related) stereo centers and are not mirror images of each other.They are not mirror images of each other. -epimers: type of diateroemr, stereoisomer that differs in configuration at any single stereo genic center-ONE site is the opposite ANY site -anomers:An annoyer is an ember at the hemiacetal/acetal carbon in a cyclic saccharide, an atom called the numeric carbon, ONE SITE is diff and that’s the numeric diff -Diasteromers: same formula and not mirror images but still superimposable, has more than one chiral center but relative to each other have AT LEAST (1 OR MORE) one chiral centers that are the same and at least one that are different, basically if they have multiple stereos with at least one diff then the other but some same. If have all diff with multiple sterecents then they are antimeres, and if they only have one different then espiers (Carbs) -epimers: type of diateroemr, stereoisomer that differs in configuration at any single stereo genic center-ONE site is the opposite ANY site -anomers:An annoyer is an ember at the hemiacetal/acetyl carbon in a cyclic saccharide, an atom called the numeric carbon, ONE SITE is diff and that’s the numeric diff -e/z or cist and trans since 2Cs used Diasteroisomers and number of stereoisomer possible - Correct Answers 2^n gives u number of stereoisomers possible where n is stereo centers geometric isomers (cist-trans) - Correct Answers isomers in which the order of atom bonding is the same but the arrangement of atoms in space is different -only applies to constrained mole (have double or triple) Alkene Diastereomers - Correct Answers A type of stereoisomerism in which different groups attached to each carbon of a C=C double bond may be arranged differently in space because of the restricted rotation of the C=C bond, -based on highest priority, and has to have some diff mole (can’t have 2 pairs of the same mole bc not isomer then), used when Cist and Trans cant apply bc have multiple subs on double bond (other THEN H, like have H, Cr, Cu, Fe etc so cist/trans cant apply so use E/Z), think of it as the double bond as a chiral center with 4 diff subs with 2 on each side and then e/z it based on priority rules: higher atomic number higher priority if equal then move to next atom outward/bonded-********Review****** -E/Z are also cist/trans isomers and diasteromers Relative v Absolute configuration - Correct Answers Relative: based on how compounds are oriented to each other (In relation to another chiral mole, used to know if die, enationmer etc but not its actual) -cist/trans +/- Absolute: configuration doesn’t change and is always that -E/Z or D/L or R/S D/L v R/S - Correct Answers -D and L simply describe the direction in which polarized light is rotated by the molecule. It applies to the molecule as a whole, but gives you absolutely no specific information about position of groups. In other words, "D" and "L" cannot tell you if a substituent is "going forward" or "going backward" in any way., D/L determination does not relate to any specific functional group (like OH or NH2), it relates to the chirality of the molecule overall. If a molecule is chiral (that is, if it is not superimposable with its mirror image), then it should rotate polarized light as a consequence. It will either rotate it to the "D" direction or "L" direction. -R and S give you specific information about position of groups on a chiral center. If you know something is in the R configuration, you know how to specifically position the groups around a chiral center in 3-dimensions. It bears note that you cannot assume if this positioning will rotate light in D or L directions... bc D/L is relative to the mole (what we want) while R/S is absolute and no variation (Ex: cysteine is L although its R) https://www.reddit.com/r/chemhelp/comments/3mbukx/determining_dl_and_rs/ R/S - Correct Answers When H on top, whatever the circle is drawn is what it is When H on side think middle guy lifted When swapping left corners v top right corner try and get H on top so you can just write the config like normal- to get lowest on top from bottom Goal is to get H on top of fisher, but if cant and only on side then its fine just remember to lift the middle guy etc -when on top then however it writes is fine, but remember when in middle just lift middle guy etc (irk about when on bottom) -when the dash/solid is point up lift middle guy and apply R/S, if it points down then act like normal and flip what you got-think u had to further rotate it to get accurate thing ----- this only applies to when the middle guy is the 1 in fisher, if you get H on top of t then don’t need to do anything****** mesa compound - Correct Answers A compound with chirality centers and an internal plane of symmetry causing it to be an achiral molecule -the plane of symmetry can be at the chiral center itself or btw chiral centers -be sure to rotate camp to make sure -made up of two halves that are mirror images of each other spa usually just applies the central atom being C, make sure u know exactly what type of spa orbitals urn looking for C, total etc. -sp2 etc tells u hybrization around a central atom, to tell number of bonds need then to actually look at their bonds not nhdrization and go based off whether it is 1 (sigma) 2(sigmpa +pi) 3 (sigma 2pi) essential sp2 hybridization tells u have double bond that is made of sigma and pi, but -hybridization=refers to orbitals (sp2 etc) -types of bonds is exactly what it is based off single double etc Conjugated double bonds - Correct Answers requires alt double single bonds, this aligns hybridized p orbitals down the backbone so that pi electrons can be delocalized in p orbitals -this provides stability and allows light to be seen.fluer with UV etc Remember - Correct Answers Orbital hybridize to give u sp3, sp2 spa bonds do not there are Sigma and Y pi bonds in a hybrid Energies within subshells - Correct Answers s<p<d<f 2n^2 - Correct Answers maximum number of electrons within a shell Resonance - Correct Answers when mole has conjugation (have unhydridized p orbitals in backbone), the pi e- delocalize through p system adding stability to the mole -true form: hybrid of all resonance structures -if stability differs then the true e- density will favor the most stable form Chapter 4: Analyzing Organic Reactions - Correct Answers Acid-Base Definitions - Correct Answers Lewis: not always H can be lone pairs -Acid: e- pair acceptors (Lewis Acid-Acceptor), aphid and has vacant p-orbital (accept e- so exhale bc gets attacked by nun) -Base: e- pair donor, nuchal and uses its lone pairs, often anions Browsed-Lowry: H involved -Acid: anything that donates H+ -Base: anything that receives/accepts H+ -Amphoteric: acts as both (water, in basic acts like acid, in acid acts like base and AlOH3, HC03-, HS03-) Lewis Acids and base interact to form coordinate covalent bonds -Remember, acid/base run will only proceed if products formed are weaker than the original reactants (conjugate base/acid) (SA to weak cob) -Anything with carbonyl easier to attach lone pair/accept it, Nh3 usually nun be lone pair pike - Correct Answers -loggia so smaller pike stronger acid (Ki 1 SA but very low pea same thing) -any pike below -2 is a very strong acid -as bond strength decreases the acidity of something increases (more likely to disso), if opposing then bond strength can outduel high electronic if has very low bond strength (electronic on table and bond strength is the weaker with bigger atoms) (bond strength decreases going down so down part is strongest acid) -there more electronegative atom the higher the acidity bc its pulling e-s away and allowing disso. -the more e- w/d groups the more acidic (electro/resonance), the more e- donating groups (CH3 etc) the more basic (e- donors helps stabilize post charge bc don’t like e-) - hydrogen connected to a-C are acidic bc the enroll form for carbonyl C (that would be an anion if lost) is stabilized through resonance so can a-C's H is acidic bc H can be lost and still form stable mole -alkane<alkene<H-H<amine (NH3)<Alkyne<ester<ketone/aldehyde<Alcohol<water<CA<h30+ E density and e= w/d - Correct Answers Carbocation’s are typically unstable due to their high concentration of positive charge. If a substituent can contribute some electron density to the carbocation, this positive charge will be "balanced" and the species stabilized. In contrast, electron-withdrawing substituents pull even more electron density away from the carbocation, decreasing its stability further. Since fluorine is destabilizing, and since it is highly electronegative, we can deduce that it must be electron- withdrawing. Nucleophiles - Correct Answers lone pairs or pi bonds that can form new bonds with exhales, tend to be good bases (bases e- donor) (nucleophiles is based in kinetics while basicity is based in thermo bc acid bases are equi based), and wants to uses its e- to make bonds -EDGs makes more nuns, donate to increase e- density and gives resonance (think basicity, bases better nukes) -more nag charge better nun -LESS electronic better nun (bc higher lecturing means less likely to donate and keep e- to itself , better nucleophiles want to share e- not hog them all (like F/O alone not good if with and EDG like R group then better)-LESS ELECTRO -less hindered, better nun (bulkier makes less nun) bc of steric -Solvent plays a role: Parotic Solvents then nun increases going down periodic table (opp trend of electro and this is normal) v APROTIC nun increases going UP periodic table (opp normal) -Aprotic(DMF, DMSO, ACETONE- can't donate H) v Parotic (CA, amines/ammonia, water and alcohol-can donate H) -I>Br>Cal>F- are good nukes in parotic (bc protons attracted to more electro and thus be less able to form bonds, think HF is we) but in aprotic then I<Br<Cal<F (this bc no protons are in the way to forming bonds) -e- donating groups makes something more nun (bc more e- to get to nun), bases also make things more nun bc it deport (bases takes away H) thus making it more nag Ammonia v Ammonium - Correct Answers Ammonia: NH3 is a web Ammonium NH4 is a we Bicarbonate is a web HCO3- Protonation - Correct Answers lone pairs allow for protonation and allows water to swap its Hz Exhales - Correct Answers e- loving usually with +charge (remember acidity is thermo product bc equi based but ephilcity is kinetic and usually acid bc takes e- since its pos (H+)) -more positive charge the more exhale(carbocation) -if there are no empty orbitals then L group makes it better exhale -EWG makes more epic bc pulls e- and reveals charge -CA can also be ranked by electrophilic, the higher reactivity derivate can form from derivate of lower (Anhydrides to CA etc), ephilicty goes from Anhydrides>CA>esters>amides -more e- w/d group makes its better exhale, -better L group better exhale bc L group can leave and leave the exhale with pos charge -More electronic the strong exhale again pulling of e- -donating more H (via Acids) makes things more exhale bc it protonates something making it more positive and thus making it more likely to attack (for nun bases bake it more nun) -ONE STEP, not stable enough to be 2 so E2 -No rearrangement carbocation rearrangement - Correct Answers - adjacent σ bond switches without base - in equilibrium, proceeds in a way that will increase stability (goal to get closer to term carbocation) E1 and SN1 ONLY bc of tart and sec carbocation Substitution or Elimination Rxns - Correct Answers -Elimination acts when L group leaves then acts to fulfill lost by making double bond, they usually occur under basic conditions like catalysts or ph., subsection involves a nun -Subsection is the swap for L group (Web) for strong nun (SB) Redox reactions - Correct Answers -Oxidation: an increase in oxidation state, loser of e- (less negative or more positive), or more bonds to Oxygen or heteroatom (atoms not H or C), bond btw C and less electronic is replaced with bond to more electronic (more electro neg other atom means more positive charge you get i.e increase oxidation state, can be to another C to form alkene) -Reduction: DECREASE in oxidation state, gain of e- (more neg), increasing number bonds to H or C more bonds to O the more oxidized it its (CO2>CA/Anhydrides/esters/amides etc) -Rxns tend to act on highest priority Fig (most oxidized) Oxidizing agents - Correct Answers -Oxidizing agents become reduced (accept e-) while the thing reduced becomes oxidized -When looking at reagents thing has lots of O so oxidizing agent itself so wants to increase more bonds to O one the reactant, in doing so gains e- because takes e- from reactants -PCC weak oxidizing agent, CrO3 3 bonds to O and KmNO4 has 4 bonds to O so strong oxidizing agent etc and can turn Alcohol into CA etc Reducing Agents - Correct Answers become oxidized and in doing so reduce the reactant they acted on -think more bonds to H ******************* Carboxylic acid derivatives - Correct Answers most oxidized, tells which gets redox/substituted then goes ketone/aldehyde -the more oxidized the C the more electronic groups around if and larger partial positive it has and more exhale it is -a-Hz are very acidic and can leave relatively easy so become nun (stabsalize into enol form) and form enolate when in presence of strong base -Steric hinderence can create a kinetic product more than a thermo product as major product cyanide to alcohol - Correct Answers the C in C=N acts as nun and attackes and extend carbon chain at carbonyl and N is kept creating an alcohol -IDK -reverb a RCN (nitrile) Nitrile to carboxylic acid - Correct Answers -reverb a RCN (nitrile) can turn into CA if hydrolyzed with throng enough acid (H2SO4) OR- V OH- - Correct Answers OR- donates more e- so stronger nun then OH- most oxidized form of carbon - Correct Answers CO2 then CA Chapter 5: Alcohols - Correct Answers Phenols v Phenyls - Correct Answers Phenyl has Ch3 on it Phenols has OH -Phenols are more acidic than Alcohols bc of the resonance in ring that stabilize O -slightly soluble in water -bc more acidic then most alcohols they can run with bases - (e-) w/d groups increase acidity while e- donating groups increase basicity (decrease acidity) (w/d pulls e- to allow disso) -they can NOT be oxidized bc not tech an alcohol electron withdrawing groups - Correct Answers strongly electronegative and pull electron density away from rest of the molecule, and stabilize negative charge. CA derivate except amides and esters CN, Ns etc Electron donating groups - Correct Answers Groups that push (donate) electron density towards another functional group through sigma or pi bonds. -anything with lone pairs and alkyl Roth, meta, Para positions - Correct Answers Due this when bonze ring has 2 subs on it Properties of Alcohols - Correct Answers Alcohols are capable of forming hydrogen bonds with each other (oxygen has high electronegativity) -more Oh more acidic (increase H bonding) -The electronic O pulls e- to from H and creates partial pos and neg and bc partial neg and pos can participate in H bonding (attraction) -more alkyl groups the less acidic (Alkyl groups are e- donating and so can stabilize pos charge and no charge is pulled) so primary more acidic then territory? Oxidation Reactions of Alcohols - Correct Answers Oxidation of alcohols can produce several products -1º alcohols can be oxidized to aldehydes-PCC (weak oxidizing agent) -1º can be oxidized into lad then be hydrated to turn into germinal dials or if using stronger oxidizing agents to turn into CA -2º can be turned into Ketone with strong or weak oxidizing agents (PCC) -3º cannot be oxidized bc have to break bond to do so -Na2Cr207 and K2Cr207 and CrO3 turns 1º into CA (anything w/o O is weak oxidizing agent) Idol Synthesis - Correct Answers Oxidizing a double bond creates dials basically adding O to double bond Germinal Idol synthesis - Correct Answers can be when carbonyl hydrated by water Germinal Idol v Idol - Correct Answers germinal Idol has Oh on same C Desolates and Tosylates - Correct Answers -Maculate: R-SO3CH3 -Tosylates: R- SO3C6H4CH3, only protect group in a Redox sense but it can increase reactivity for sub that can also act as make it more reactive in another sense (sub) Creating Aldehydes and Ketones - Correct Answers -1º alcohols can be oxidized to aldehydes-PCC (weak oxidizing agent) -1º can turn into germinal dials or CA with stronger oxidizing agents -2º can be turned into Ketone with strong or weak oxidizing agents (PCC) -Don’t have to worry about oxidizing ketone to far bc can’t go passed ketone bc 2C so can use any oxidizing agent Aldehyde ad Ketone Addition Reactions - Correct Answers bc partial positive on carbonyl C then good for nun attack bc good exhale -when nun attacks it forms cove bond and breaks pi double bond and e- from pi bond are pushed to O2 and oxygen happily accepts it and tetrahedral intermediate forms -When carbonyl pi bond broken think can I reform carbonyl and that is based on if there is a good L group, if no good L group then it will form an OH instead of remaking carbonyl but if good L group then carbonyl will reform ad push L group out (remember good L group is weaker nun then nun attacking, L groups usually WB) Hydration Reactions of Aldehydes and Ketones - Correct Answers when water present with acid or base catalyst they form germinal idol (2 OHs on 1 C) Aldehydes and Ketones + alcohol - Correct Answers form acetyls and hemiacetal when -1 equivalent of alcohols forms hemi-acetyl -2 equivalents of alcohols form acetyl Mach: nun attack by alcohol to carbonyl then form hemi, then remaining hydroxyl groups gets protonated then turns into water and leaves carbocation, then Second alcohol comes in and attacks and same steps happen in which 2 OR groups added to make acetyl -SN1 and uses anhydrous catalyst -The diff btw hemiacetal and acetyl is that hemi still has OH and OR while acetyls have 2 OR groups -Acetyl v germinal idol is that OR v OH Imines and Examines - Correct Answers Immunes: simplest way is when NH3 or NH2-R uses its lone pair and attacks carbonyl and forms double bond to C, carbonyl and O2 lost as H20 so this is condensation reaction and nun subsection Examines: same much but Uses NHR2, or if NH3 used it can tautomirze and turn into examine HCN - Correct Answers great nun bc has triple bond to C and electro N making it slightly acidic (pulls e- away and makes H deport easier) -HCN (cyanide) +keno/lad form cyanohydrins and relatively stable C is the attacker Oxidation and reduction of aldehyde ad ketones - Correct Answers Chapter 7: Aldehydes and Ketones II Enolate - Correct Answers Based on the a-C inland and ketones acidity of alpha hydrogen’s - Correct Answers bc of induction, 02 pulls some e- density out of the a-CH bond which weakens it and this makes it easy to deprotonate the a-C and the acidity is then furthered amplified by the ability for resonance to stabilize the carbonic CB -when H removed from a-C the extra e- that remain lay btw the a-C and carbonyl C and makes an enolate intermediate and so neg charge can go to Oxygen or to a-C -Note: the Keota a-C is less acidic bc the extra alkyl group acts as e- donating in ketone and so destabilizes the carbonation -Note: aldehydes more reactive to nun than ketones bc of hinderence ad high E intermediate less likely to form DONE THROUGH DEPROTONATION RXN (strong base like Noah, LDA or KH or acid catalyst) -basically, deport and then when it becomes neg it can then start attacking other lad/ketones bc acts as an enolate Enolate formation - Correct Answers these intermediates must be generated in high concentration in the absence of other strong nucleophiles and bases (these guys would want a sub situation run and they are better at sub rxns bc better nun, to make these guys nukes u need to NOT have better nukes around) -essentially formed by the loss of the H+ a-C, think about it enolate teats to make the neg either in the O or C so in order to make it to the C u need some deport on the a-C, BUT this can be done by acidic conditions (port the O so that the CB can deport the a- C) or basic (remove the H directly from a-C) The aqueous base conditions used for the ado condensation are not suitable because the enolate anions of simple carbonyl compounds are formed in very low concentration, and hydroxide or lakeside bases induce competing SN2 and E2 reactions of alkyl halides -Common bases: LDA, NaNH2, Noah w/ THF solvent keno-enol tautomerization - Correct Answers key is Enol not Anole -end mesa double bond while AN means straight alkyl chain keno-enol tautomerization. - Correct Answers enol means C-C double bonded with a C attached to alcohol hence -old and the keno form differs from enol based on the where the H ad double bond is moves to -equi usually favors Kato version but to go to enol version it has to tautomirze, so normally O attacks unless taut happens -when an a-C is a chiral center it will most likely form a racemic mixture -Taut can also happen with the anhydrides -LDA or KH can deport and form carbonation and then that neg charge can bounce around through taut and that neg charge attacks e pile can also be done through acid catalyst s -Mikhail Addition ex of using this -Examines can also taut remember -enolate means Oxygen is negative ad double bond btw a-C and carbonyl, when carbonation is favored is in anhydrides bc delocalized by 2 O2s Kinetic and Thermodynamic Control - Correct Answers - The kinetic enolate forms more quickly, it’s for irreversible, low temp, satirically hindered base(bigger bases), and is less stable than the thermodynamic enolate. (less hindered most), faster bc easier/less steric to deport the less subs C - Thermodynamic forms more slowly, for: products are reversible/they interchange btw each other,/reversible rxns, weaker or smaller bases, higher temperature (more hindered forms less product) -Remember this is based on the product Kinetic and Thermodynamic Enolate - Correct Answers - The kinetic enolate forms more quickly, irreversible, low temp, satirically hindered base, and is less stable than the thermodynamic enolate. - Thermodynamic forms more slowly, reversible, weaker or smaller bases, higher temperature Kinetic v Thermo Control - Correct Answers -kinetic control, it is said that the preferred product/major output product of the reaction is the one that is formed most quickly and has the lowest activation energy barrier(hence kinetic). Even though the other products may be more stable, we see that the major species post-reaction will be the product