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How can you predict an acid base reaction?
- The reactant with the lowest pKa value is the acid and will lose a proton.
- The reactant with the highest pKa value is the base and will gain a proton.
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Which side is favored during equilibrium?
The side with the weaker acid is favored because it is the most stable.
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What determines the strongest acid?
- -if the atoms are similar in size (RO, RC, RF) then the most electronegative atom is the strongest acid
- -if the atoms ar different in size (HCl, HF, HI) then the largest atom is the most acidic
- -if a halogen is closer to the substiuent
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Dipole Dipole interactions
Electrosatic forces in which the partial charges attract each other
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Hydrogen Bonds
when the hydrogen attache to an electronegative atom is attracted to the lone pairs of F O N
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What has a higher boiling point, compounds with odd or even C atoms?
Even because they can match up in a symmetrically packed way
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Solubility Rules
-like dissolves like (polar dissolves polar: nonpolar dissolves nonpolar)
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At what point are alcohols insoluble in water?
An alcohol can drag about three carbons.
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Isomers
Compounds with the same molecular formula but different structures.
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Constitutional Isomers
These isomers differ in the way that they are connected.
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Cis and Trans Chair Conformer
Cis has the groups or atoms facing the same direction while trans is the opposite (up / down)
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Chair Conformer:
-axial bonds
-equatorial bonds
- Axial Bonds: the straight bonds of a chair conformer (like an x or y axis)
- Equatorial Bonds: the ones that are diagonal on a chair conformer
- -more stable for the conformer to be in the equatorial position than the axial
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Steric Strain
The strain that occurs on the molecule when atoms or groups are close enough to repel each other.
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Anti Conformer vs. Gauche
- Anti: When the methyl / other functional groups are as far away from each other
- Gauche: That is when the functional/ methyl groups are near each other (less stable - more energy)
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Staggered vs. Eclipsed Conformer
Staggered has the bonds no overlapping, but an eclipsed conformer has the atom bonds overlapping
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Conformer
The different spacial arrangements that occur from rotation about a single bond
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Which halides are most soluble in water?
The one with F is the most soluble and normally slightly soluble for the other halogens.
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Which amines are most soluble in water?
Primary amines because the hydrogen's can participate in hydrogen bonding, while tertiary amines can't go through hydrogen bonding.
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At what point are ethers insoluble in water?
The become slightly soluble with 4 carbons and insoluble at 5/6 +
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Stereoisomers
Atoms are connected in the same way and the only difference is that the atoms are arranged in space differently
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Cis and Trans Isomers
- When the direction the atoms are facing is different in a molecule (wedge / dash)
- Cis - same
- Trans - different
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Chiral vs. Achiral
- Chiral Molecules: mirror images of each other
- Achiral Molecule: have a superimposable mirror image that makes the mirror image the same as the original
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What is the cause of chirality?
An asymetric center: an atom that is bonded to four different groups (also called stereocenter - all asymetric centers are stereocenters but not all stereo centers are asymetric)
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Enantiomers:
A chiral molecule and it's mirror image
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How do you rank for an R, S naming?
Atoms with the highest atomic number have the highest priority.
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Equation to determine enantiomeric excess
Observed Rotation / specific rotation of pure enantiomer x 100%
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Racemic Mixture
a mixture of equal amounts oftwo ena
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Diastereomers
Stereoisomers that are not enantiomers
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Meso Compound
Even when the molecule has asymetric senters, it has a superimposable mirror image making it achiral
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Degree of Unsaturation
The number of pi bonds and ring compounds in a structure
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Naming using the E,Z system
- Z: high priority groups are on the same side
- E: high priority groups are on opposite sides
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Electrophile vs. Nucleophile
- Electrophile: has a positive charge, a partial positive charge, or incomplete octet
- Nucleophile: has an extra electron, or electrons it can share (-)
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Transition State (reaction diagram)
Highest peak on the reaction pathway in which bonds are being formed and broken
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Endergonic vs. Exergonic reaction (how do you know which one is faster when compared?)
- Endergonic: change in G is (+) in the end
- Exergonic: (-)
- -the fastest of each is the one with the smallest free energy of activation (change in G double dagger)
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Carbocation
An organic compound with a positive charge on a carbon
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Rate Determining Step
The step in which has the highest transition state
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Ketone vs. Aldehyde
- Ketone: has a double bonded O coming from a tertiary carbon
- Aldehyde: has a double bond carbon coming from a secondary or primary carbon
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Most stable alkene...
One with as much C's attached to double bond
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Regioselective
A reaction in which two constitutional isomers are obtained but more of one is formed than the other.
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Stereoselective
A reaction in which two sterioisomers are formed but one is formed more than the other.
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To remove a proton from a molecule, what substance must you use?
A base stronger than the acid so it can accept the proton rather than have one taken away.
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Acidity increases in what kind of C-C bonds?
Triple Bonds: Because the bond is tighter, the electrons are closer to the atoms and pulled away from the hydrogen giving it an easier time to be pulled away by a base
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With resonance structures, when electrons can be moved into multi directions, which one is the most stable resonance contributor?
The one in which the electrons move towards the most electronegative atom.
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What three features decrease the predicted stability of a resonance contributor?
- -atom with incomplete octet
- -negative charge on an atom that is not the most electronegative
- -charge seperation
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Why doesn't benzene undergo normal alkene reactions?
Benzene is an extremely stable compound due to it's large delocalized energy
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Kinetic Product
The more rapidly formed product. (more = kinetically controlled)
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Thermodynamic Product
The more stable product. (More = thermodynamically controlled)
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Reversible and Irreversible conditions in making a Kinetic or Thermodynamic product.
- Irreversible: the product is kinetically controlled because it is the fastest to be produced (looooow temp)
- Reversible: the product is thermodynamically controlled because if the kinetic product is formed, it can be reversed and eventually become a thermodynamic product which is more stable and stays together better (high temp)
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1,2 addition v. 1,4 addition
1,2 addition is always the kinetic product, but the 1,4 addition is not always the thermodynamic product because the thermodynamic product can also be a 1,2 addition.
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For a Diens-Alder reaction, what confirmation should the Diene be in?
- A cis confirmation
- -any thing locked in trans - reaction will no
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