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