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Formal Charge: Zf=Nval+Nbond-2Nlone+Nodd Dipole = charge x distance moment = e xd If no dipole μ=0D

For resonance structures only positions of e- change

Ester

Leaving group = always a species that takes a SN2 reactions always occur with pair of e- with it Amine: inversion of configuration. SN1 occurs with intermediates, not transition states.. Alkane= no multiple bonds. Ends in –ane ALKYL HALIDES

Rules for Resonance: Want all octet structures A – formal charge is favored by more electronegative atoms (O,F) Charge separation decreases stability Resonance is e- delocalization; stabilizes

Alkene= have C=C. End in –ene Akyne=have C triple bonds. End in -yne Light atoms vibrate at higher frequencies than heavier ones and stiffer bonds vibrate at lower frequencies than less stiff bonds

Nitrile: R-C=N

Cis = same Trans = opposite

Primary alkyl x attached to C attached to 1 other C Secondary alkyl x attached to C attached to 2 other C Tertiary alkyl x attached to C attached to 3 other C

L. Acid: e- pair acceptor Ether: Lewis Base: e- pair donor Nucleophile = Lewis base Carbonyl: Bronsted Acid: substance Aldehyde: that can donate a proton Polar molecules have higher boiling points Bronsted Base: a Having more s substance that can accept Acidity Constant pka = -logKa character meansKetone: Ka = [H3O+][A-] / [HA] a proton that the e- of the Phenyl is a C6H5CH2 Acid-base rxns always Larger pka means weaker acid anion will be lower functional group benzyl group favor the formation of in E and the anion Alcohol -ol High molecular symmetry = high (ring) the weaker acid and will be more stable # of chain always melting point base begins at end near Clockwise = R rotation The curved arrow begins with a covalent bond or unshared egroup named as Tert-butyl: -diol= 2 OH Counterclockwise = S rotation suffix pair and points to a site of e- deficiency
Alkane CH3-H Methane CH3CH2-H Ethane CH3CH2CH2-H Propane CH3CH2CH2CH2H Butane Akyl Group CH3Methyl CH3CH2Ethyl CH3CH2CH2Propyl CH3CH2CH2CH2Butyl

IHD: Halogens = H O ignored N ignored and –1H

When a ring Isopropyl: Cyclo substituent is = ring Melarger than the Achiral (identical other the mirror image) Etconformation with Acidity increases along molecules not R and S period (electronegative optically active IHD is defined as the Prpriority a, b,the larger one difference in the number effect). Acidity increases c, d based equatorial is more down a group (bond stable Phenyl halides unreactive in Sn2 of pairs of H atoms Buon atomic # No obvious correlation exists between the between the compound strength effect). at first point S and R configurations of enantiomers andunder study and an Polarizer Carbocation stability: of difference the direction in which they rotate plane- acyclic alkane having Clockwise (+) = dextrorotatory
Abbreviation Counterclockwise (-) = levortatory the same number of carbons. Protic: % enantiometric excess = [(Moles of 1st enantiomer – moles of 2nd enantiomer) / total moles ] x 100 has H = [observed specific rotation / specific rotation of pure enantiomer] x 100 Aprotic: no H 3°>2°>1°>methyl Reactivity opposite for SN2 polarized light

Basicity of hydrocarbons: H3C-CH2- > H2C=CH- > HC triple bond CAcidity of hydrocarbons: HC triple bond CH > H2C=CH2 > H3C-CH3

[α]= α/C x L C = concentration of solution in g mL-1 L = length o cell in decimeters (1dm = 10cm) Diastereomer = stereoisomer not mirror image Enantiomer = stereoisomer mirror image

Alkenes (Alkynes -yne) Cis less stable than trans because steric clash. 1. Determine parent name by selecting the longest chain that More stable configuration if atoms are distant from Aprotic doesn’t hinder nuc. contains the double bond and change the name if the alkane of one another Naming Branched-Chain Alkanes # of Const. Isomers Through h-bonds Alkane identical length from –ane to –ene 1. Locate longest chain; parent name 2 CnH2n+2 2. # chain so includes both C=C and begin # of chain near C=C. C4H16 Acyclic Alkenes 2. # of Cs beginning at end closest to the substituent 3 Cyclo Designate location of C=C by using the # of the 1st atom of the C5H12 CnH2n+2 3. Designate location of substituent (Parent name 5 CnH2n double bond as a prefix. The location of the alkene may precedeC6H14 last, substituent name + # first) C7H16 9 the parent name or be placed immediately before the suffix 4. When 2+ substituents on parent, give each chain a C8H18 18 3. Indicate the location of the substituent groups by # of Cs Physical Properties # corresponding to location on chain (listed they’re attached to alphabetically) 4. # substituted cycloalkanes in a way that gives the C=C the 1 Branching lowers the BP because it reduces 5. When 2 substituents are on same C, use # twice and 2 positions and give the substituents the lowest # at first the surface area of the molecule so dispersion forces don’t work as well. 6. When identical substituents use prefix di-, tri-, point of difference Even # C molecules melt at higher tetra-, etc. 5. Alcohols called alkenols temperatures than odd # C molecules 7. When 2 chains = # Cs, one with more substituents 6. cis and trans (unbranched) (even more compact than odd) is parent chain Van Der Waals electrical Dipole-dipole forces: results from Usually branching produce symmetry = 8. When branching occurs at = # distance from either dipole moment + end orient toward – end higher MP end of longest chain, choose name that gives lowest # H bonds: dipole-dipole between H and very Solubility “like dissolves like” at 1st point of difference electronegative elements (F, O, N) Diastereomers = different BP, MP, Newman Projection Dispersion solubilities, etc. Larger molecules Enantiomers = same BP, MP, staggered confirmation solubilities , etc. more stable due to Vinylic group: repulsion of e- clouds of Alkynes and bonded groups Alkadienes During a transition state, a C atom (2 = bonds) Comounds who are undergoes an inversion. (ALWAYS in Sn2 CnH2n-2 Constitutional isomers Meso compound: stereometric due to reaction.) are different compounds chirality centers, total achiral molecule with Protic nucleophilicity: (Also best L.G.): I->Br->Cl->Fthat have stereoisomers won’t chiral centers. Not Aprotic nucleophilicity: F-> Cl->Br->Ithe same molecular optically active. exceed 2n. (n = total formula but differ in chiral centers) Endergonic: + free-energy change connectivity The transition state 1. A negatively charged nucleophile is Exergonic: - free-energy change Bicycloalkane resembles the stable always a more reactive nucleophile than its conjugate acid. Increase T, increase collisions, Bridged Fused species that is nearest it 2. In a group of nucleophiles in which the nucleophile atom is increase free-energy in free energy the same, nucleophilicity parallels basicity.

2 shift where a group moves Aprotic solvents do not Dehydrohalogenation: α C: contains leaving group from 1 C to the adjacent C contain H bonded to Alkene can also be reprotonated in order to create electronegative atom. one is H2O) alkyne alkynes occurs when they are treated Cis  enantiomers α C  bonds to functional group Hydrogenation of alkynes in the presence of P-2 When a reaction that can Retrosynthetic analysis: work from target β C  next to the α C catalyst causes syn addition of hydrogen. substitution results  temp = E1 and E2 favored over SN1 and SN2 Using a sterically hindered base favors elimination too Substitution of acetylenic H with other groups is through SN2 reaction syn addition: addition takes place on same side of reactant anti addition: addition takes place on opposite sides of reactant Heterogeneous catalysis: the substrate is soluble in the reaction but the catalyst is not Homogenous catalyst: the catalyst is soluble in the SN1 Reactivity: reaction mixture Sodium amide = NaNH2 (Strong Z = like cis. . opposite side Stereospecific rxns: (instead of 2 halogens binding to Can remove terminal H from Anti addition of hydrogen to the triple bond of Trans  mesocompound alkene. same side (less stable) 3° only (in non acidic conditions) Halogenation in H2O  halohydrin base) E = like trans. anticoplanar transition state preferred constitutional isomers Electrophiles  e. When the nucleophile attacks the carbon atom bearing the leaving group. Uses THF the reaction is said to be Acetoxymurcury group: regioselective. When the nucleophile (base) attacks a b hydrogen atom.anti-Markovnikov addition: H bonds to C with least H Oxidation and hydrolysis of alkylboranes takes place with retention of configuration Anti-Markovnikov Sulfuric acid: Acid catalyzed hydration Gem-dihalide: (used to make alkynes) Hyperconjugation: e. potentially yield two or more molecule backward until reach starting compound In E2 rxn. β C: adjacent to alpha C a more stable alkene arrangement Dimethyl sulfoxide: Solvolysis: SN1 with H2O Larger atom means better nucleophile Methanolysis: SN1 with methanol SN2 and E2 reactions are both favored by a high concentration of a strong nucleophile or base.delocalization (via 1˚ alcohols follow E2 rxn b/c charge Ketones can be converted to orbital overlap) from a filled bonding least effectively delocalized and gem-dihalides with PCl5 orbital to an adjacent unfilled orbital carbocation is highly unstable 2˚ alcohols can have 1.seeking actually produces only one Oxymercuration-demercuration of alcohols avoids agents aka Lewis acids rearrangement (or a predominance of one). elimination occurs.