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orgo 1
| Question | Answer |
|---|---|
| 2 ELECTRON DOMAINS | sp; 180 |
| 3 ELECTRON DOMAINS | sp2; 120 |
| 4 ELECTRON DOMAINS | sp3; 109.5 |
| sigma bonds | end to end overlap of ANY orbital |
| p bonds | sideways overlap of P orbitals |
| When u think of a pi bond think of | p orbital |
| H bonded to a c = | s |
| Protic solvent= | capable of hydrogen bonding--- so all you need is FON |
| LOW BP= | SHORTEST CHAIN, HAS BRANCHING ( b/c branching lowers SA and BP) |
| FREEZING POINT/ MELTING POINT= | OPPOSITE OF BP |
| pH= | pKa |
| STRONGER ACID= | INC Ka; DEC pka |
| Stronger base= | DEC Ka; INC pKa |
| NOT polar= | hydrocarbons and benzene |
| stable base= | weaker base/ less reactive |
| weaker acid/ base= | same side |
| weaker acid= | higher pka |
| rank acids based on looking at ____ | their conjugate base |
| rank bases based on ____ | their base |
| more negative= | stronger base |
| more positive= | stronger acid |
| ranking acids based on congugate base use: | CARIO- (Charge, Atom, Resonance, Dipole Induction, Orbitals) |
| most resonance stabilized= weakest conjugate base= | = strongest acid |
| dipole induction for a conjugate base | find most electronegative atom based on elecrtonegativity for a base |
| In cardio when looking at orbitals look at : | (stongest acid) sp > sp2> sp3 (weakest acid/ most stable conjugate base) |
| amide | RCO-NH2 |
| AMINE | R-NH3 |
| sigma (s) ____ stable; ____ energy | more; less |
| pi (p) _____stable; ____energy | less; more ( more reactive) |
| percentages of sp | 50% s 50% p |
| percentages of sp2 | 33%s, 67% p |
| percentages of sp3 | 25% s; 75% p |
| LOW VP= | high BP |
| constitutional isomer | aka structural; have diff bond connectivity |
| sterioisomers | same bond connectivity, but diff 3D arrangement |
| i.e. of sterioisomers | cis/ trans and chiral ( has a enationmer) centers |
| Enatiomers | optically active; same physical properties ( BP,MP), but differ in optical activity ( rotations) |
| optical activity is tested by | polarized light ( + or -) NOT ( R and S) |
| racemic mixture | 50/50 ; doesnt rotate light, optically incactive |
| Nucelophile | electron rich/ e- donor ( lewis base) ; - charge best |
| Most nucleophiles are negative in charge except | N and P ; which are still good nucleophiles |
| nucleophilicity in protic solvent= | I is most |
| nucleophilicity in aprotic solvent= | F is most |
| electrophile | lewis acid( e- pair acceptor, e- poor) + charge is best |
| alkyl halides/ carbonyl/ cyan= | great electrophile b/c have good leaving groups |
| carbocations stability | 3>2>1>methyl |
| carbanions | electron rich; methyl>1>2>3 |
| allylic positions= | carbocation is one bond away from a double or triple bond ( pi) |
| Benzylic posistion= | carbocation is one bond away from a benzene |
| oxidation on a ring= | 2 new bonds to MORE electronegative atoms ; i.e. F Br CL |
| Reduction on a ring= | 2 new bonds to LESS electronegative atoms; i.e. H |
| saturated | has as many H as it could possibly have |
| Degrees of unsaturation | every 2 H your missing from saturated alkane ( CnH2n+2)= 1 degree of unsaturation |
| i.e. C6H12 is missing 2 H to make an alkan...so thats | 1 degree of unsaturation |
| i.e. C6H13N = missing 1 H to make an alkane ... so thats | 1 degree of unsaturation |
| i.e. C6H13CL= | saturated...because of the halogen |
| gauche | has any 2 non hydrogen groups adjacent to each other in a staggered conformation |
| gauche stability | FEWER gauche interactions u have = the more stable u are. |
| gauche stability | THe smaller the size of the gauche substituents= more stable |
| a triangle ( cyclopropane) = | most reactive= least stable= most ring strain |
| The most stable of the cycloalkanes= | cyclohexane ( 109.5) = least ring strain; least reactive; most stable.....SO the closer you are to cyclohexane ( except for cycloheptane)....the stabler u are |
| EQUATORIAL= | most stable |
| cis and trans on a chair conformation deal with... | up and down ( DO NOT worry about cis and trans) |
| more exothermic= | least stable; more ring strain |
| free radical halogenation (bromonation) | add halogen to most substituted C. MARKINOV |
| Chlorination | non selective and everything is favorable, so we have a lot of products |
| Progagation ( keep radical party alive) what is favorable? | chlorination |
| initiation = ENDO or EXO | ENDO....using energy to break bonds...not favorable |
| phenol= more or less acidic than alcohol? | phenol is MORE acidic b/c of resonance |
| W.A.S | Withdrawing groups make Acids Stronger |
| Withdrawing groups= | make bases weaker |
| Donating groups= | make bases stronger |
| ortho and para= | more acidic than meta |
| No group is more acidic in rank than | donating |
| Is OR more acidic or NR3 | OR= more acidic than NR3 because N is less elecrtonegative ( gives up e- easier aka more donating) than O....making N less acidic |
| if you get a planar carbocation during SN1 it will give u... | a racemic mixture (chiral) b/c it can attack from the dash or wedge |
| if u double amnt of neutrophhile and electrophile (halide) in SN2, then the rate? | quadrupules |
| if you double amount of electrophile (halide) in SN1, then the rate? | does not change |
| SN2 rxn: | strong nuc; methyl>1>2 and 3 doesnt react at all; polar APROTIC solvent |
| SN1 rxn: | weak nuc; 3>2 ( NO 1 for SN1) ; polar PROTIC solvent |
| APROTIC= | acetone, DMSO , DMF, ethers |
| PROTIC= | H2O; Alcohol; Carboxylic acids |
| Leaving Groups= | I>Br>CL> F |
| SN1 has a carbocation...so it can do rearrangement but... | SN2 can NOT....it can howerver do 100% inversion |
| Primary Benzylic can do SN1 or SN2, so to determine which one, just look at | the solvent |
| Aryl halide attached to SP2 C can not do | SN1 or SN2 |
| CH3OH | does solvolysis (SN1 rxn only) |
| is product goes through SN1 and it is NOT chiral, then | DONT WORRY ABOUT racemic mixtures |
| NUCELOPHILE STRENGTH :: | on the top of the periodic table....arrow points to C;; ON SIDE OF TABLE for APROTIC = ARROW POINTS TO F; for PROTIC arrow point to i |
| for a nucleophile strength in a protic solvent (SN1) | I is the best (strongest) |
| for a nucleophile strength in a APROTIC solvent (SN2) | F is the best (strongest) |
| E2 differs from SN2 because | it can do tertiary |
| E1 differs from SN1 because | base deprotanated unlike SN1 |
| Heat favors which rxn? | E1. if no heat was added then it could be both SN1 and E1 product |
| E1... | attacks most substituted C to make most substituted alkene |
| E1 has a | carbocation intermediate like SN1 |
| E2 rxn | needs strong base; 3>2>1; Aprotic |
| E1 rxn | needs weak base; 3>2; Protic |
| anticoplanar | point up and down |
| Anti Zeiseff/ Hoffman product | make least substituted alkene |
| Zeiseff product | make most substituted alkene |
| bulky base ( weak nucleophile/ no good) + strong base | E2 |
| strong nucleophile + weak base | SN2 |
| Bulky base= | do E2 |
| strong nucleophiles | NaCl, NABr, NAI, NaCN, NaN3 |
| if u have a primary halide... | you will have major SN2 product and minor E1 product |
| 1. Hg(OAc)2, H2O 2. NaBH4 | 1. add mercury and O 2. Take off mercury and add a H to the O |
| B= | good nucleophile b/c it is e- poor |
| BH3, THF or B2H6 | does ANti Markinov, adds B |
| syn addition | same side addition to form an alkene |
| H2 & pd/c | take out double bond; reduces alkenes and alkynes to alkanes |
| H2 & pd/c, BaSO4, quinoline | reduces alkynes to alkenes |
| alkene with H2 and lindlars catalyst has | NO rxn |
| aromatic rules | 1. cyclic 2. huckels rule of 4n+2 3. Unhybridized P orbital 4. sp2 planar ( no wedges or dashes) |
| 4n+2, n= | 2,6,10,14,18 |
| Anti Aromatic | doesnt follow huckels rule |
| Non aromatic | non cyclic, non sp2 planar, no unhybridized P orbital |
| radical induced addition.... | use ANTI markinov ....boronation |
| ketones make | weak acids and strong bases |
| aldehyde makes | strong bases and weak acids |
| acidity ranking | ester<ketone<aldehyde |
| Keto Enol Tautomerization | readily interconvert from a ketone to a enol (alkene + alcohol) |
| hydration | adds H20 |
| Hemiacetal/ HemiKetal | starts with aldehyde or Ketone and makes OR-C-OH |
| ketone + primary amine (RNH3) = | Imine(schiffs base) C=NR |
| Grignard ( CH3MgBr) cant react with | H2O or OH- |
| Ketones + gringard = | add a H to the =O and whatever is infront of the -MgBr on the same carbon as the OH |
| CH3-Li | Does the same thing grignard does |
| When deal with an ester and a grignard, u need ___ moles of grignard | 2 moles |
| Michael RXN | nucelophile can attack at B carbon |
| aldol condensation (add alpha cabon to B carbon) | n is an organic reaction in which an enol or an enolate ion reacts with a carbonyl compound to form a β-hydroxyaldehyde or β-hydroxyketone, followed by a dehydration to give a conjugated enone. |
| aldol condensation EZ way | take the reactant at the B carbon and add the nucleophile to it at the alpha carbon of one of them, so that it is double bonded to it,,and erase the O from one of it |
| ketone + OH- ---> | self aldol condensation , so assume 2 moles of ketone |
| We do ELectrophilic Aromatic Substitution to benzene rings because | doing addition to a benzene ring would make it non aromatic |
| Chlorination | Cl2, AlCl3 |
| Nitration | HNO3, H2SO4 |
| Sulfonation | SO3, H2SO4 |
| Iodination | I2, HNO3 |
| aldehydes and ketones undergo | nucelophilic addition reactions |
| esters and amides undergo | nucleophilic acyl substitution |
| alkenes and alkynes undergo | electrophilic addition |
| aromatic | electrophilic substitution |
| aldehyde has an alpha H, so in dilute acid or base do,,,, | ALDOL CONDENSATION ( assume 2 moles of aldehyde) |
| Aldol condensation can only occur if you have a | alpha- hydrogen |
| + TOllen's test means | Either Aldehyde or alpha hydroxy ketone |
| + 2,4- DNP test means | Carbonyl group |
| Acids attack? | most substituted C |
| Bases attack? | Least substituted C |
| suffix of an ester | -oate |
| RO- K + | makes double bonds |
| BH3, THF/ H2O2, OH- | adds OH in enationmer fashion |
| Which alcohol dehydrates the fastest? | tertiary (3) |
| something is saturated when.... | it is an alkane and has ALL of it's H's |
| # of sterioisomers= | 2^N ; where N = number of chiral centers |
| Radical reactions for propagation steps | (EXO) F2> Cl2>Br2> I2 ( endo) |
| Vibration creating highest frequency at | triple bonds> double> single.....conjugation decreases vibration frequency |
| Absorb UV light= | molecule with most conjugation= most stable= gives off most color |
| weakest IR signal= | one with NO dipole |
| Lewis acids ( ALCl3) are nucleophiles of electrophiles? | electrophiles |
| less electronegative= | electrons are more LOOSELY held |
| K2Cr2O7 | Makes =O |
| O3 Ozonolysis/ Zn/H3O+ | breaks alkene/alkyne and makes =O |
| At low temp (KINETIC), a conjugated diene will give us | 1,2- addition |
| At high temp (thermodynamic) , a conjugated diene will give us | 1,4- addition |
| NBS/ROOR removes the_____ | allylic hydrogen( the H next to the double bond) and adds Br to it. |
| Alkanes undergo | radical substitution |
| allene= optically active = | c=c=c |
| cycloalkane & alkenes= | CnH2n |
| alkynes | CnH2n-2 |
| Inorder to do E2 on a ring, you have to have both groups opposite eachother.....in a ____ position | CIS; the halogen has to be in the axial position in chair conformation, and the r group has to be in the equatorial position in chair conformations |
| SN1 | Rate= K ( halide) |
| SN2 | Rate= K (halide) (nucleophile) |
| LiALH4, Et2O, H30+ with a NITRILE = | reduces the nitrile to a PRIMARY AMINE |
| If u have a Hemiacetal in a sugar ring, then | 1. Mutatorate 2. Reducing Sugar 3. + Tollens and Benedicts test |
| D-sugar = | The CH2OH is ABOVE the pane of the ring |
| PCC | mild oxidizing agent. Turns 1 OH into aldehydes and 2 oh in ketones |
| Diazomethane = | CH2N2 ; Will add across the double bond and make a 3 membered ring |
| Low heat of hydrogenation= | most stable alkene= 3 alkene |
| HgSO4/H2O, H2SO4 | Take an alkyne and change it to an enol( alkene + OH) . Then does a tautomeric shift to make a ketone (looses the OH and makes an alkane) |
| ESTER + Grignard= | ALWAYS Assume 2 moles of grignard |
| aldehyde + OH-, H2O, Heat= | ALdol condensation. Assume 2 moles of aldehyde and take off h2o. |
| Acyl halide ( RC=O-X) + Primary Amine ( NH2-R) = ? | Amide ( R-C=O- NH-R) |
| MOST EASILIY DISSOLVE IN WATER =? | something with alot of hydrogen bonding (i.e. RCOOH) |
| williamson Ether synthesis | IS A SN2 reaction. It works best with primary halides!! |
| Grignard= | powerful BASE. removes protons from an element. Cant work with diethylether. |
| at physiological pH, the COOH is in what form? | COO- |
| at physiological pH, the NH2 is in what form? | NH3+ |
| aryll halide (benzene with an X ) = does it do SN1 or SN2? | NEITHER!!! |
| What LOWERS BP? | BRANCHING...because SA decreases |
| lowest BP for an amine? | the answer choice with the least amount of N bounded to H and that is NOT ionic ( ionic= highest BP) |
| Most reactive in nuceleophilic Acyl Substitution | Acyl halide> Anhydride> thioester> amide> ether |
| What transforms C=O into an alkane? | Wolf- Kishners reduction [ (NH2NH2, OH-, heat)] and Clemensens Reduction [(Zn(Hg), HCL] |
| to extract an acid, use a | BASE (NaOH or NaHCO3) |
| to extract an amine, use a | ACID ( HBr) |
| to extract a phenol, use a | BASE ( NaOH) |
| In NMR, the closer a atom is to an electronegative atome (i.e. Oxygen), the more downfield it has= | higher number on the scale. |
| least stable= | + sign on a EWG (i.e. NO2) |
| most stable= | + sign on a EDG (i.e. CH3) |
| + sign CAN NOT be located on | a Carbon with 4 bonds |
| Hoffman rearrangement (need a primary amide + Br2, base (OH-) ) | primary amide looses the C=O (one fewer carbon atom) to become an amine. |
| H3PO4 (phosphoric acid) + N2+ CL- ( diazonium salt) = | takes off the N2+ CL- from the ring completely. |
| NaNO2, HCL added to a NH2= | Changes the NH2 into a Na+ CL- (diazonium salt) |
| Sn, HCL, OH- reacted with NO2 will make | change NO2 into NH2 |
| More substitued ( stable) alkene has :: | 1. LOWEST heat of hydrogenation & combustion |
| Fatty Acid formula | Cn H2n O2 |
| Dieckman Condensation (diester treated with a strong base) = | makes a 5 to 6 membered ring & ( RO- and an alpha H) is lost. |
Created by:
zrsoori
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