Organic Chemistry

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  1. Isomers
    Same molecular formula, but different structures.
  2. Isomers that differ in connectivity
    • Structural (Constitutional) Isomers: differ in connectivity (only share molecular formula)
    • Steroisomers: have the same connectivity
  3. Conformational Isomers
    Same molecules but differ in the rotation around a single bond.

    • Newman Projection
    • Staggered: when the molecules don't line up in a Newman Projection
    • Anti Staggered: two largest molecules are antiparrallel
    • Gauche: two largest molecules are 60 degrees apart
    • Eclpised: when there is overlap of substituents and two largest groups are 120 degrees apart
    • Totally Eclipsed: direct overlap of largest substituents
  4. Cyclic Conformational Isomer Strains (3 total)
    • Angle Strain: results when bond angles deviate from ideal behavior (cyclohexane most ideal)
    • Torsional Strain: strain when ring has to undergo eclipsed or gauche interactions
    • Nonbonded Strain (Van Der Waals Repulsion): steric strain
  5. Cyclohexane Conformers
    Can be chair, boat, or twist-boat cyclohexane. It can also undergo a chair flip with chair conformers. The most stable conformer is when the largest substituents are equitorial. Can be cis or trans, but you have to look at no chair version of it.

    • Equitorial: off to the sides
    • Axial: up an down
  6. Chirality
    • Chiral: has a nosuperimposable mirror image. They are also optically active.
    • Achiral: superimposable mirror
  7. Classifying two molecules with nonsuperimposable mirrors
    • Diastereomers: chiral and share same connectivity but NOT mirror images. They have different chemical and physical properties.
    • Enantioners: mirror images of each other. They have similar chemical and physical properties  but polarize light differently. (d- is + ; l- is -)
  8. Specific Rotation Equation
    Standard rotation for chiral enantiomers.

    (specific rotation) = (observed rotation in degrees)/(concentration * path length)
  9. Configuration, and two types of Configuration
    Configuration: spacial arrangement of atoms.

    • Relative Configuration: configuration in relation to another chiral molecule
    • Absolute Configuration: exact spacial arrangement of atoms independent of other molecules
  10. Nomenclature of substituents on double bonds
    It is based on atomic number, not the group as a whole. You must also go Carbon to Carbon deciding highest priority.

    • E: epposite sides
    • Z: zame sides
  11. Chiral Center Nomenclature
    • Have the thumb face the hydrogen.
    • R: right hand spin
    • S: left hand spin

    When assigning priority, H is always 4
  12. Fisher Projection R/S Designation
    X-axis are wedges, Y-axis are dashed lines

    To bring the lowest away from you, turn the molecule 180 degrees (NOT 90 degrees) or swap x-axis 1 with y-axis 1 and x-axis 2 with y-axis 2
  13. Optically Active
    Ability of a molecule to rotate plane-polarized light.

    • d- or (+) rotate light to the right
    • l- or (-) rotate light to the left
  14. Racemic Mixtures
    Contains equal concentrations of enantioners. They also cancel each other out making the mixture NOT optically active.
  15. Calculating max number of stereoisomers
    • 2n
    • n = stereocenters
  16. Lewis Acid / Base vs Bronsted-Lowry Acid / Base
    • Lewis Acid: electron acceptor (electrophile with a positive polarization)
    • Lewis Base: electron donor (nucleophile with a negative polarization)
    • Bronsted-Lowry Acid: proton donor
    • Bronsted-Lowry Base proton acceptor
  17. Amphoteric
    A molecule that can act as an acid or a base.

    • H2O
    • Al(OH)3
    • HCO3-
    • HSO4-
  18. Acid Dissociation Constant
    Measure of the strength of the acid. Higher the Ka value, stronger the acid.

    Ka = [H+][A-]/[HA]
  19. pKa
    • pKa = -logKa
    • -2 and lower: strong acid
    • -2 to 20: weak acid
    • 20 and higher: strong base
  20. How does bond strength affect acidity?
    Bond strength decreases going down a periodic table. This means that there is a higher chance of an acid donating a proton, such that acidity increases.
  21. How does electronegativity affect acidity?
    The more electronegative the atom, the more electrophilic it is, the more acidic it is.
  22. Alkane pKa
    ~50
  23. Alkene pKa
    ~43
  24. Hydrogen Gas pKa
    42
  25. Amine pKa
    ~35
  26. Alkyne pKa
    25
  27. Ester pKa
    25 (R-COOR)
  28. Ketone / Aldehyde pKa
    20-24
  29. Alcohol pKa
    17
  30. Water pKa
    16
  31. Carboxylic Acid pKa
    4
  32. Hydronium Ion pKa
    -1.7
  33. Acidic Functional Groups
    • Most Carboxylic Acid Derivatives
    • Alcohols
    • Aldehydes
    • Carboxylic Acids
    • Ketones
  34. Basic Functional Groups
    Amides and Amines
  35. Nucleophiles
    Nucleus loving molecules that make good bases. Nucleophile strength is based on kinetics, NOT thermodynamics.
  36. How are nucleophilicity trends affected by solvent type (protic / aprotic)?
    • Polar Protic: can hydrogen bond; nucleophilicity increase ↓ a period (the weaker nucleophile would want to form more bonds with the protons in the solution causing it to not access the electrophile)
    • Polar Aprotic: cannot hydrogen bond; nucleophilicity increase ↑ a period (no protons attacking nucleophile so they are free to attack electrophile)
  37. Common Protic Solvents
    • Protic: can hydrogen bond (polar)
    • -carboxylic acids
    • -ammonia
    • -amines
    • -water
    • -alcohol
  38. Common Aprotic Solvents
    • Aprotic: cannot hydrogen bond (nonpolar)
    • -DMF
    • -DMSO
    • -acetone
  39. Strong Nucleophiles (4 characteristics of good nucleophiles)
    • 1) the more (-) charged nucleophile is best
    • 2) the less electronegative nucleophile is best
    • 3) less substituted nucleophile best
    • 4) if the solvent is aprotic, it increases strength of nucleophile (it doesn't provide protons that deter effects of nucleophiles)

    • HO-
    • RO-
    • N3-
    • CN-
  40. Fair Nucleophiles (x2)
    • NH3
    • RCO2-
  41. Weak Nucleophiles (x3)
    • H2O
    • ROH
    • RCOOH
  42. Better Electrophile Determination
    • -stronger acid
    • -higher (+) charge
    • -more electronegative
    • -better leaving group
  43. Leaving Groups
    They are the molecules that take all the electrons during a heterolytic reaction (a reaction where bonds break, and all electrons from that bond move towards one atom).

    The best leaving groups are weak bases (conjugate bases of strong acids). Strong bases are too nucleophile's to want to leave the molecule. They are also molecules capable of resonance for stabilization.
  44. Nucleophilic Substitution Reactions
    A reaction in which a necleophile attacks a molecule, causing a leaving group to leave. The attacking nucleophile must be a stronger base than the leaving group.
  45. SN1 Reaction
    -Rate determining step
    -Primary product formed
    -Configuration of attacked molecule prefer-ability
    • Unimolecular Nucleophilic Substitution Reaction
    • Two step reaction:
    • 1) leaving group leaves forming a carbocation
    • 2) nucleophile attacks

    • Rate determining step: the formation of the carbocation is the rate determining step. This means that the rate depends on substrate concentration.
    • rate = k[R-L]

    Primary product formed: racemic mixture produced because nucleophile can attack either side.

    Configuration of attacked molecule prefer-ability: the more substituted the carbocation, the more stable it is, the more favored SN1 is
  46. SN2 Reaction
    -Rate determining step
    -Primary product formed
    -Configuration of attacked molecule prefer-ability
    • Bimolecular Nucleophilic Substitution Reaction
    • Single step reaction.
    • 1) the nucleophile conducts a back sided attack

    • Rate determining step: since it only has one step, the rate falls on the entire reaction. This also means that the rate depends on both substrate, and nucleophile.
    • rate = k[R-L][nuc]

    Primary product formed: since it is a back side attack, the product has an inverted configuration if the attacking group has the same bond order

    Configuration of attacked molecule prefer-ability: SN2 reactions prefer molecules that are less substituted. This is because substitued reaction only produces more steric hindrance.
  47. What is PCC capable of?

    -primary and secondary alcohol
    Turning a primary and secondary alcohol into an aldehyde or ketone.

    (Good Oxidizing Agent)
  48. What is CrO3/pyridine capable of?

    -primary and secondary alcohol
    Turning a primary and secondary alcohol into an aldehyde or ketone.

    (Good Oxidizing Agent)
  49. What is H2CrO4 capable of?

    -aldehydye
    -alcohol
    Turning an aldehydye or an alcohol into a carboxylic acid.

    (Good Oxidizing Agent)
  50. What is KMnO4 capable of?

    -aldehyde
    -alcohol
    -benzene
    Turning an aldehyde, alcohol, and a benzene with a methane attached into a carboxylic acid.

    (Good Oxidizing Agent)
  51. What is H2O2 capable of?

    -aldehyde
    Turning an aldehyde into a carboxylic acid.

    (Good Oxidizing Agent)
  52. What is KMnO4, Heat H3O+ capable of?

    -alkene
    -alkyne
    Turning an alkene with one carbon having one substituent and the other having two, into a ketone and a carboxylic acid.

    Turning an alkyne into two carboxylic acids.

    (Good Oxidizing Agent)
  53. What is 1) O3 2) Zn capable of?

    -alkene
    Turning an alkene into two ketones.

    (Good Oxidizing Agent)
  54. What is 1) O3 2) CH3SCH3 capable of?

    -alkene
    Turning an alkene into two ketones.

    (Good Oxidizing Agent)
  55. What is 1) O3 2) H2O2 capable of?

    -alkene
    -alkyne
    Turning an alkene with one carbon having one substituent and the other having two, into a ketone and a carboxylic acid.

    Turning an alkyne into two carboxylic acids.

    (Good Oxidizing Agent)
  56. What is OsO4 capable of?

    -alkene
    Turning an alkene into OH groups on both sides (cis)

    (Good Oxidizing Agent)
  57. What is KMnO4, HO- capable of?

    -alkene
    Turning an alkene into OH groups on both sides (cis)

    (Good Oxidizing Agent)
  58. What is mCPBA capable of?

    -alkene
    -ketone
    Turning an alkene into an epoxide

    Turning a ketone into an ester

    (Good Oxidizing Agent)
  59. What is NaIO4 capable of?

    -Diol (2 cis alcohol groups on adjacent carbons)
    Diol (2 cis alcohol groups on adjacent carbons) splits in two forming an aldehyde

    (Good Oxidizing Agent)
  60. What is Pb(OAC)4 capable of?

    -Diol (2 cis alcohol groups on adjacent carbons)
    Diol (2 cis alcohol groups on adjacent carbons) splits in two forming an aldehyde

    (Good Oxidizing Agent)
  61. What is HIO4 capable of?

    -Diol (2 cis alcohol groups on adjacent carbons)
    Diol (2 cis alcohol groups on adjacent carbons) splits in two forming an aldehyde

    (Good Oxidizing Agent)
  62. What is LiAlH4/NaBH4 capable of?
    Turning an aldehyde or a ketone into a primary or secondary alcohol.

    (Good Reducing Agent)
  63. What is 1) LiAlH4/ether 2) H+/H2O capable of?
    Turning an amide (like a carboxylic acid except the single bonded O group is N) into a primary amine (No O groups)

    (Good Reducing Agent)
  64. What is 1) LiAlH4/ether 2) H2O capable of?

    -carboxylic acid
    -ester
    Turning a carboxylic acid into a primary alcohol.

    Turning an ester (O=C-O-R) into two primary alcohols.

    (Good Reducing Agent)
  65. Good reducing agent?
    They have low electronegativities and low ionization energies.

    • H-
    • Sodium
    • Aluminum
    • Zinc
    • Hydrides like NaH, CaH2, LiAlH4, NaBH4
  66. Good Oxidizing Agents?
    High oxidation state and bigger love for electrons.

    • O2
    • O3
    • Cl2
    • MnO4-
    • CrO42-
    • CrO72-
    • PCC
  67. How can you tell which carbon is more oxidized?
    It is the carbon with the most highest electronegative groups attached to it.
  68. Where is a redox reaction more likely to attack?
    It has a higher chance of reacting with the highest priority functional group because it contains the most oxidized carbon.

    So it is more likely to react with a carboxylic acid, than an alcohol.
  69. How can you protect a ketone such that a chemical won't react with it?
    You can add in a diethanol and H+ to the molecule. It causes the carbon attached to the ketone to bond to lose the alcohol and attach to both alcohols (now ethers).

    Acts as a protecing group.
  70. What are the two reactive centers of a carbonyl-containing compounds?
    • 1) Carbonyl carbon because it is very electrophilic
    • 2) α-H attached to the adjacent carbonyl carbon because it is very acidic due to resonance
  71. How does conjugation play into stability?
    A more conjugated carbon is much more stable. This means that in a reaction, an organic compound is less likely to form something that is less conjugated because it is less stable.

Card Set Information

Author:
DianaKarlova
ID:
320315
Filename:
Organic Chemistry
Updated:
2016-05-26 07:58:50
Tags:
MCAT Organic Chemistry
Folders:
MCAT
Description:
MCAT Study Cards
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