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Organic Chem

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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