MCAT OChem

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nextMD
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192070
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MCAT OChem
Updated:
2013-01-13 15:44:55
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MCAT Princeton OChem Chapter
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MCAT Princeton OChem Chapter 3
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  1. sp hybrid orbital
    s character
    p character
    bond angle
    molecular geometry
    • 2 attached atoms or lone pairs
    • s - 50%
    • p - 50%
    • bond angle - 180o
    • molecular geometry - linear
  2. sp2 hybrid orbital
    s character 
    p character
    bond angle
    molecular geometry
    • 3 attached atoms or lone pairs
    • s - 33%
    • p - 67%
    • bond angle - 120o
    • molecular geometry - trigonal planar
  3. sp3 hybrid orbital
    s character 
    p character
    bond angle
    molecular geometry
    • 4 attached atoms or lone pairs
    • s - 25%
    • p - 75%
    • bond angle - 120o
    • molecular geometry - tetrahedral
  4. Sigma () bond
    • bond of two electrons that are localized between two nuclei
    • Ex: sp- sp3  bond
  5. Pi () bond
    • composed of two electrons that are localized to the region that lies on opposite sides of the plane formed by the two bonded nuclei and adjacent atoms, not directly between the two nuclei as with  bonds
  6. saturated organic molecule
    • contains 2n+2 hydrogen atoms
    • n = number of carbon atoms
  7. degree of unsaturation
    • [(2n+2)-x]/2
    • n=number of carbons
    • x = number of hydrogens (or halogens, such as F, Cl, Br, or I).  For N replace with 1C and 1H.
    • Oxygen is ignored
  8. constitutional isomers
    same molecular formula, but atoms are connected together differently
  9. conformational isomers 
    same molecular formula, same atomic connectivity, but differ from one another by rotation about a single  bond
  10. anti conformation
    in a Newman projection, it represents the lowest energy conformation, in which the two largest groups are at 180apart
  11. gauche conformation
    when the two largest groups on adjacent carbon atoms are in a staggered conformation 60o apart
  12. stereoisomers 
    are molecules that have the same molecular formula and connectivity but differ only in the spatial arrangement of atoms
  13. chiral
    a molecule that cannot be superimposed on its mirror image
  14. achiral
    a molecule that can be superimposed on its mirror image
  15. chiral center, stereo center, stereogenic center or an asymmetric center
    has four different atoms bonded to it, the carbon must be sphybridized with 109bond angles and tetrahedral geometry
  16. number of possible stereoisomers in a molecule
    2- where n = chiral centers
  17. enantiomers
    • non-superimposable mirror images
    • can be formed by inverting every stereocenter
    • chemical properties and physical properties are identical between enantiomers
  18. optically active
    a compound that rotates plane-polarized light
  19. dextrorotatory (d) (+)
    a compound that rotates plane-polarized light in the clockwise direction
  20. levorotatory (l) (-)
    a compound that rotates plane-polarized light in the counterclockwise direction
  21. racemic mixture - racemate
    50/50 mixture of enantiomers, 0% specific rotation
  22. diastereomers
    • stereoisomers that are not enantiomers,
    • they are stereoisomers that are non-superimposable, non-mirror images
    • inverting one, but not all chiral centers will form a diastereomer
    • physical and chemical properties can vary dramatically between diastereomers
  23. epimers
    • a subclass of diastereomers that differ in their absolute configuration at a single chiral center (only 1)
    • Ex. Two sugar epimers which vary only at the four carbon are considered C-4 epimers
  24. anomers
    • Epimers that form as a result of ring closure
    • Can be either alpha (OH is up) or beta (OH is down) at C1
  25. meso compound
    • one side of a molecule (that contains a chiral center) is the mirror image of the other side
    • meso compounds have no optical activity
  26. geometric isomers
    • diastereomers that differ in orientation of substituents around a ring or a double bond
    • trans
    • cis
  27. Z and E
    • used for double bond same side/opposite side relativity
    • Compare 2 highest priority groups on each side of the double bond
    • Z - same side
    • E - opposite side
  28. melting point/boiling point rules
    • increasing branching decreases melting point and boiling point
    • increasing molecular weight increases melting point and boiling point

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