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Organic Chem
| Question | Answer |
|---|---|
| Ketone: Structure | C-C-C ll O |
| Ester: Structure | O ll l -C-O-C- l |
| Ether: Structure | l l -C-O-C- l l |
| Aldehyde: Structure | O ll C-H |
| Carboxylic Acid | O ll C-OH |
| Primary Amine: Structure | l -C-NH2 l |
| Nitrile: Structure | C=-N (triple bond) |
| Primary Amide: Structure | O ll C-NH2 |
| Thiol:Structure | l -C-SH l |
| Thioether:Structure (Sulfide) | l l -C-S-C- l l |
| Phenyl:Structure | C=C / \ C C \\ // C-C |
| Alkyl Halide:Structure | l -C-X l |
| Epoxide:Structure | O l l C-C |
| Peroxide:Structure | X-O \ O-X |
| Sulfoxide:Structure | O ll S / \ |
| Boronic Acid:Structure | HO OH \ / B l |
| Tert-Butanol | OH l CH3-C-CH3 l CH3 |
| Isopropanol | CH3 / OH -CH \ CH3 |
| n-Propyl | C-C-C-n |
| Neopentyl | CH3 l CH3-C-CH2-n l CH3 |
| Sec-butyl | CH3CH2CH-n l CH3 |
| Tert-butyl | CH3 l H3C-C-n l CH3 |
| Isopropyl | CH3 \ CH-n / CH3 |
| n-butyl | C-C-C-C-n |
| Benzoic Acid | CO2H l C = C / \ C C \\ // C-C |
| Phenol | OH l C=C / \ C C \\ // C-C |
| Toluene | CH3 l C=C / \ C C \\ // C-C |
| Aniline | NH2 l C=C / \ C C \\ // C-C |
| Nitrobenzene | NO2 l C=C / \ C C \\ // C-C |
| Benzoic Acid | CO2H l C=C / \ C C \\ // C-C |
| Succinic Acid | O O ll ll HO-C-CH2CH2-C-OH |
| Carbonic Acid | O ll HO-C-OH |
| Acetic Acid | O ll CH3-C-OH |
| Formic Acid | O ll H-C-OH |
| SN1 Reaction | -Monomolecular Nucleophilic Substitution. -Involves Carbocation Intermediate (rate determining step) -Racemization of configuration when a chiral molecule is involved |
| E1: Rate determined By: | Concentration of only ONE compound |
| SN2 Reaction: | Bimolecular nucleophilic substitution 2nd Order -Rate determined by concentration of TWO compounds Nu(-) + R-L --> {Nu---R---L} --> Nu-R + L(-) Backside replacement |
| Hemicetal Production Mechanism | Hydrogen Attacks O (partial neg) -->creates carbocation -H from alcohol quickly attacks carbocation, expels proton ---> recreates catalyst |
| Carbanion | C(-) |
| Carbocation | C(+) |
| Oxidation | Increasing Oxygen content OR decreasing Hydrogen content |
| Alpha Particle | Doubly positively charged helium nucleus |
| Steric Factors | Large or bulky groups near a reaction site that hinder the reaction's progression |
| Substitution Reaction | One atom or group is substituted (replaced by another) |
| Salts | Ionic compounds that conduct electricity and are crystalline solids at room temperature |
| Amphoteric | A substance that can act as both an acid and a base |
| pH | Measure of acidity -log [H(+)] |
| Lewis Acid | Substance accepting electrons |
| Lewis base | Substance donating electrons |
| Bronsted-Lowry Base | Substance that accepts a proton |
| Bronsted-Lowry Acid | Substance donating a proton |
| Secondary alcohol + CrO3/K2Cr2O7/KMnO4 | Ketone |
| Primary alcohol + KMnO4 --(under abrasive conditions)--> {acidic/in presence of -OH} | Carboxylic Acids |
| Mild Oxidizing Agents | CrO3 K2Cr2O7 or KMnO4 @ room temperature + neutral pH |
| Major Product | Most stable of the possible products of a reaction |
| Minor product | Less stable of the possible products of a reaction |
| Alcohols | An alcohol is any organic compound in which a hydroxyl group (-OH) is bound to an alkyl or substituted Alkyl group IR abs: 3200-3650 (KNOW THIS) |
| Ortho | (of rings) 1,2 |
| Meta | (of rings) 1,3 |
| Para | (of rings) 1,4 |
| Angstrom | 10 ^ -10 Meters |
| Aromatic Compounds | Cyclic compounds which have their pi electrons delocalized across the whole ring |
| Alkene (definition) | An unsaturated chemical compound containing at least one carbon-to-carbon double bond |
| Axial Substituents | These substituents (generally) perpendicular to the ring |
| Equatorial Substituents | Those in the same plane as the carbon ring |
| Nucleophile | Molecule with a free pair of electrons and sometimes have a negative charge ex: OH(-), CN (-) |
| Electrophiles | Substances which seek electrons |
| Achiral | Optically Inactive |
| Configuration | Absolute three dimensional arrangement |
| Specific Rotation | An inherent physical property of a molecule, measuring the rotation of plane polarized light by a substance. Observed rotation (degrees) Alpha= --------------------------------- (Tube Length (dm)) x (Concentration (g/ml) |
| Dextrorotary | A substance that rotates plane polarized light in a clockwise direction |
| Levrorotary | A substance that rotates plane polarized light in a counterclockwise direction |
| Meso Compound | Achiral (optically inactive) disastereomer of chiral stereoisomers |
| Plane Polarized Light | Light that oscillates in only one plane |
| Carbonyl Group | C=O |
| Markovnikoffs Rule | The nucleophile will be bonded to the most substituated carbon. The Electrophile will be bonded to the least substituted carbon |
| Benefits of H2O | High Heat Capacity, High heat of vaporization, polar solvent properties, Reactivity, Cushions organs |
| Radical Propagation | Free radical begins a series of reactions creating new free radicals. CH4 + Cl * --> *CH3 + HCl *CH3 + Cl2 --> CH3Cl + Cl* |
| Acetal | Composite functional group in which two ether functions are joined to a C bearing a H and an alkyl group |
| Ketal | Composite functional group in which two ether functions are joined to a carbon bearing two alkyl groups |
| Hemiacetyl/ Hemiketal | OH l R-C-R' l OR'' R' determines ketal/acetal |
| Aldol Condensation | A base catalyzed reaction of aldehydes and ketones that have alpha hydrogens. Intermediate Aldol: Alcohol + Aldehyde Aldol undergoes a dehydration reaction producing C-C bond in condensation product, and enal |
| Enal | Aldehyde + Alkene |
| Aldol | Substance which is both aldehyde + alcohol |
| Gringard Reagent | RMgX |
| Alkyl Lithium | RLi |
| Carboxylic Group | R-C=O l OH |
| Dimerization | Hydrogen bonding between like substances |
| Oxidizing tertiary alcohols | -Difficult process Under acidic conditions, a tertiary alcohol can be dehydrated, hen oxidized |
| Good "leaving groups" have | Strong conjugate acids |
| 'E' designation | Substituents on a double bond and given priority. If two highest priority groups are on opposite sides, it is assigned E configuration E=entegegen=Opposite |
| Radical Substitution Reactions (steps) | -initiation -propagation -termination |
| Ozonolysis | Oxidation of alkenes O3 reacts vigorously with alkenes -Leads to an oxidative cleavage of double bond, creating a ketone and an aldehyde |
| Acidity of alpha hydrogen | Alpha hydrogen is attatched to the carbon next to the carbonyl group. It's acidity increases if in between carbonyl groups |
| Naming of ketones/aldehydes | Replace "e" of corresponding alkane with: -'al' for aldehydes -'one' for ketones |
| Naming an alcohol | Replace the 'e' of corresponding alkane with '-ol' |
| SN1 Reaction Rates for Carbon (groups) | Benzyl=Allyl >tertiary > alcohols > secondary alcohols > primary alcohols |
| Enantiomers | Two non-superimposable diastereomers which are mirror images of one another. -must be chiral |
| A substituent is a "good leaving group" if | It has a strong conjugate acid |
| Benzene's C-C bond | Only known to have one type, with a bond length of 1.4 A |
| Electron Shell Repulsion | All atoms (thus, molecules) are surrounded by an electron shell, or electron cloud. Since like charges repel, the negative charges repel one another |
| Isomer | Different molecules with the same number and type of atoms |
| Conformational Isomers | Isomers which differ only by the rotation about multiple single bonds (or just one single bond) |
| Structural Isomer | (aka constitutional isomers) Isomers in which atoms and/or bonds differ in relation to one another |
| Stereoisomers | Different compounds with the same structure differing only in spacial orientation of atoms |
| Geometric Isomers | Isomers that occur in rings and alkenes due to their inability to rotate. Results in Cis/Trans compounds |
| Diastereomer | Any pair of stereoisomers that are NOT enantiomers. -Both chemically and physically different from one another |
| E2 Reactions | Require strong bases like KOH or the salt of an alcohol. (sodium alkoxide) Rate determined by concentration of TWO reactants |
| Important features of SN1 reactions in alcohols | First Order Racemization if chiral molecule Stable carbonium should be involved |
| Electrophilic Aromatic Substitution | Similar to SN1 mechanism -Occurs with electrophilic reagents and leads to a rearrangement which produces a substitution -Intermediate positive charge stabilized by resonance |
| Bromination | Br/FeBr3 is used to generate the Br+ species which is highly electronegative (can react w/ aromatic rings) |
| C=C / \ C C + E(+) ------> \\ // C-C | 3 Products differing in relative positions of E and C(+) E Cannot be on carbocation, only three locations for C(+) relative to double bond are possible. |
| Dehydration of Alcohols (Mechanism) | Proton (H+) is attracted to negative charge of -OH, forming a water which is a good leaving group. ---> electrons are attracted to the positively charged carbon causing a proton to leave, forming an alkene |
| Alcohol substitution reaction | The -OH group is replaced (substituted) by a halide (usually Cl or Br) 2 Types: SN1/SN2 Reagents: HCl, HBr, PCl3 |
| Elimination Reactions | Occur when an atom or group of atoms is removed(eliminated) from adjacent carbons, leaving a multiple bond. C-C ---> C=C |
| Alkene electrophilic addition | Electrophile is added to alkene via a carbocation intermediate |
| Alkene Oxidation | Alkene + KMnO4 (under acidic conditions) creates a dialcohol (glycol) Under extreme heat, an oxidative cleavage of double bond occurs |
| Alkene Hydrogenation | Alkenes react with hydrogen in the presence of a variety of metal catalysts (ex: Ni, Pd, Pt) |
| Electrophile in aromatic substitution | Must be a powerful electrophile -b/c resonance stabilized ring is resistant to most types of routine chemical reactions |
| SN1 reaction in alcohols | Transition state involves a carbocation, whose formation is the rate determining step -benzyl, allyl, primary, secondary alcohols - all use this mechanism |
| SN2 Reaction | -Mechanism by which primary alcohols are substituted -2nd Order -Nucleophile adds to backside -inverts configuration if optically active -Steric factors affect reaction rate |
| E2 Reaction Mechanism | 1. Base eliminates proton, giving carbon a negative charge 2. Electron pair quickly attracted to other carbon's partial positive charge (b/c of Br electronegativity) forming a double bond while Br is bumped simultaneously b/c carbon can only have 4 bonds |
| E1 Reaction | Rate of reaction depends upon the concentration of one compound. Can occur as a minor reaction alongside SN2 reaction or as a major produc in alkyl halides or some alcohols |
| Meta Directors: Mechanism | Partial positive charges are located at the ortho and para positions with no substituents, forcing the electrophile to the meta position in avoidance of positive charge |
| Carbocation/Carbanion + Bond location relative to substituent | Carbanion l Dbl Bond locations 2 l 3,5 4 l 2,5 6 l 2,4 |
| Meta directors | -Deactivating groups which slow reaction relative to unsubstituated Benzene -Withdraws electrons from ring, making it less attractive to electrophiles -Works through carbanion |
| O/P Directors | Activating group donates electrons to ring, giving the group a pos charge, and one carbon on the ring a neg charge. Neg charge is passed along the ring until group's initial double bond is broken. -Causes a reaction rate increase rel. to benzene |
| Important factors of carboxylic acid chemistry | H is weakly acidic b/c of partially neg O, and resonance Carboxyl carbon was susceptible to Nu(-) attack Good(in acid, great) leaving group H bonding is possible inner or intra molecularly |
| Low molecular weight acids: characteristics | Liquids with strong odors and high boiling points. -due to polarity + H bonding of molecule H Bonding = water soluble |
| R,S System | R configuration: Clockwise rotation after prioritization S Configuration: Counterclockwise order of priority |
| Combustion Equation | C(n)H(2n+2) + Excess O2 -----> nCO2 + (n+1)H2O |
| Ring Strain | Results from the bending of the bond angles in greater amounts than normal |
| Carbocation Stability | Tertiary>Secondary>Primary |
| Cyclohexane Stability | Chair Conformation > Boat Conformation -99% in chair conformation |
| ------------> OH(-)/H2SO4/H2O | Oxidizer Adds double Bond |
| ------------> 2NaNH2/H3O(+) | Forms third bond Turna alkene to alkyne |
| H2O/H2SO4 ------------> HgSO4 | Hydration Adds -OH and H(+) groups |
| KOH -------------> Ethanol | Oxidizer Creates 2nd/3rd bond |
| 1.Hg(OAc)2, H2O/THF ------------------> 2. NaBH4 | Dehydration Adds alcohol Group |
| Meta Position Deactivators: | -CHO O ll COH O ll COCH3 |
| O/P Activators | -CH3 -NH3 -OH |
| Ortho/Para Deactivators | -Br -F -Cl -I |
| Aromatic Rules: | 4n+2 pi electrons -conjugated ring |
| -RCONR2 | Carboxamide |
| SN2 reactivity by carbon placement | Tertiary>Secondary>Benzene>Primary>Methyl -Due to increasing ability of incoming group to access carbon -Decreasing steric interaction |
| Leaving group reactivity | OH>NH2>F>Cl>Br>I>TosO(-) -based on electronegativity |
| O3 OR KMnO4 ------------> | Oxidative cleavers Break completely between two carbons Internal C=C : Terminal C=C: C=O + C=O O=C=O + O=C=O l l OH OH |
Created by:
Tclark89
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