Organic Chemistry Test 2

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bnpusey
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236488
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Organic Chemistry Test 2
Updated:
2013-09-23 11:16:01
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Organic Chemistry Stereochemistry Alkenes Alkynes Resonance Dienes
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Covers chapters on Stereochemistry, Alkenes, Alkynes and Resonance-Dienes
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  1. Achiral
    A molecule or object that contains a plane or point of symmetry
  2. Ant Addition
    an addition reaction in which the two added substituents add to opposite sides of the molecule
  3. Asymmetric center
    • an atom that is bonded to four different substituents
    • aka stereocenter
  4. Chrial Carbon
    a Carbon which is bonded to 4 different substituents
  5. Chiral Catalyst
    a catalyst that will cause the synthesis of one enantiomer in great excess over the other
  6. Chromotography
    a separation technique in which the mixture to be separated is dissolved in a solvent and the solution is passed through a column with adsorbent stationary phase.
  7. cis isomer
    the isomer with substituents on the same side of a cyclic structure or the isomer with the hydrogens on the same side of the double bond
  8. trans isomer
    the isomer with substituents on opposing sides of a cyclic structure or the isomer with the hydrogens on the opposing sides of the double bond
  9. configuration
    the 3-dimensional structure of a chiral compound.  The configuration is designated by R or S.
  10. Configurational isomers
    • stereoisomers that can not interconvert unless a covalent bond is broken.  
    • Cis/trans and isomers with asymmetric centers are configurational isomers
    • aka geometric isomers
  11. constitutional isomers
    • molecules that have the same molecular formula but differ in the way the atoms are connected
    • aka structural isomers
  12. dextrotatory
    • the enantiomer that rotates the plane of polarization of plane-polarized light in a clockwise direction
    • D-
    • (+)-
  13. Disteromers
    • stereoisomers that are not enantiomers
    • RR vs RS
    • SS vs SR
  14. Enantiomerically pure
    only one enantiomer is present in a enantiomerically pure sample
  15. Enantiomeric excess
    how much excess of one enantiomer is present in a mixture of a pair of enantiomers, expressed in a percentage
  16. Enantiomers
    • Non Superimposable mirror-immage molecules
    • RR vs SS
    • RS vs SR
  17. Enzyme
    a protein that catalyzes a biological reaction
  18. Erythro Enantiomers
    • the pair of enantiomers with similar groups on the same side when drawn in a fisher projection
    • Distereomers to threo form
  19. Isomers
    non identical compounds with the same molecular formula
  20. Fisher Projection
    • Method of representing the spatial arrangement of groups bonded to an asymmetric center.
    • Organized so that the most highly oxidized group is at the top.
    • The horizontal lines represent bonds that project out of the plane of paper towards the viewer.
    • The vertical lines represent bonds that project out of the plane of paper away from the viewer.
  21. Levorotatory
    • Enantiomers that rotate the plane of polarization of plane-polarized light in a counter clockwise direction
    • L-
    • (-)-
  22. Meso Compound
    a compound that has chiral centers AND a plane of symmetry.  It overall achiral because of the plane of symmetry, and therefore has no optical activity
  23. Optically active
    rotates the plane of polarization of plane polarized light
  24. Persoective Formula
    • a filled in wedge indicate the bond is coming towards you
    • A dashed wedge indicates the bond is going away
    • a straight line indicates its on the plane
  25. Plane of Symmetry
    • All achiral molecules have this
    • an imaginary plane that bisects a molecule into pieces that are a pair of mirror images
  26. Polarimeter
    an instrument that measure the rotation of the plane of polarization of plane-polarized light
  27. Racemic mixture
    a mixture of equal amounts of a pair of enantiomers (aka racemate)
  28. R Configuration
    an arrow drawn from the highest priority group to the next highest goes in a clockwise direction
  29. S Configuration
    an arrow drawn from the highest priority group to the next highest goes in a counter clockwise direction
  30. Receptor
    a protein or other compound that binds a particular molecule
  31. Regioselective
    Describes a reaction that leads to the preferential formation of one constitutional isomer over another
  32. Relative Configuration
    configuration of one compound relative to another
  33. Resolution of a Racemic Mixture
    seperation of a racemic mixture into the individual enantiomers
  34. Specific Rotation
    the amount of rotation that will be observed for a compound with a concentration of 1.0 g/mL in a sample tube of 1.0 decimeter long
  35. Stereoisomers
    Isomers that differ in the way the atoms are arranged in space
  36. Stereoselective
    describes a reaction that leads to the preferential formation of one stereoisomer over another
  37. Stereospecific
    Describes a reaction in which the reactant can exist as strereoisomers and each stereoisomeric reactant leads to a different stereoisomeric product
  38. Syn Addition
    an addition reaction in which the two substituents add to the same side of the molecule
  39. Threo Enantiomers
    • A pair of enantiomers with similar groups on opposite sides when drawn in a fisher projection 
    • Distereomer to erythro form
  40. Arrange in order of oxidation:

    1) aldehyde
    2) methyl
    3) aromatic / alkyne
    4) ketone
    5) carboxylate
    6) condensed aromatic / hydroxyalkyl
    7) methylene / alkene
    • 2) methyl
    • 7) methylene / alkene
    • 3) aromatic / alkyne
    • 6) condensed aromatic / hydroxyalkyl
    • 1) aldehyde
    • 4) ketone
    • 5) carboxylate
  41. Stereogenic Carbon
    Tetrahedral carbon with 4 different froups attached
  42. Arrange in order of oxidation:

    1) -CHOH
    2) -CH3
    3) -COOH
    4) -CH2OH
    5) -CHO
    • 2) -CH3
    • 4) -CH2OH
    • 1) -CHOH
    • 5) -CHO
    • 3) -COOH
  43. Sequence Rules
    • Used to determine E/Z configuration and R/S rotation
    • 1) Higher atomic number has higher priority
    • 2) If higher priority can not be decided on first atom follow the path of next highest atom
    • 3) Expand multiple bonds by replicating the atoms attached to each end of the bond
  44. Which is Erythro and which is threo form?
  45. Descripbe D-Glucose
    • "ta-to-ta-ta"
  46. Which one is alpha-D Glucose and which is Beta-D-Glucose?  How can you tell?
    • For alpha the OH is in the axial position, for Beta it is in the equatorial position.
  47. Relative configuration
    • D- versus L-
    • Look to fisher projection lowest horizontal substituent
    • If the -R group is on the left its L-
    • If the R- group is on the right its D-
  48. Absolute Configuration
    • R- vs S-
    • The actual configuration about a stereocenter, uses the sequence rule
    • clockwise is R
    • counter clockwise is S
  49. Specific Rotation
    • (+) vs (-)
    • Specifies whether the compound is dextrotatory or levototory when placed in a plarimeter
  50. Name the Amino Acid:
    • Glycine
    • R=H
  51. Name the amino acid:
    • Alanine
    • R=Ch3
  52. Name the Amino Acid:

    • Valine
    • R=CH(CH3)2
  53. Functional Group:
    Amino Acid

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