Organic Chemistry

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bnpusey
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211140
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Organic Chemistry
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2013-08-19 14:29:53
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Organic Chemistry Nomenclature
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Memorization for organic chem
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  1. Alkane
  2. Alkene
  3. Alkyne
  4. Ketone
  5. Aldehyde
  6. carboxylic acid
  7. Ester
  8. Acid Halide
  9. PEroxy acid
  10. Amide
    • Carboxcylic Acid
    • Anhydride
  11. Primary Amine
  12. Secondary Amine
  13. Tertiary Amine
  14. Alcohol
  15. Ether
    • Thiol
    • mercaptan
  16. Benzene
  17. Benzyl
  18. Phenyl
    • Peroxide
    • technically hydrogen peroxide
  19. Epoxide
  20. Carbonmate
  21. Ketal
  22. Acetal
    • Thiol ether
    • sulfide
  23. Ionic Bond
    Results from a transfer of electrons
  24. Covalent Bond
    results from sharing of electrons
  25. Orbital
    a region of space where an electron is likely to be found
  26. Pauli Exclusion Principle
    only two electrons can occupy any atomic orbital, and to do so these two must have opposite spins.  These electrons in opposite spins are said to be paired.
    • Linear
    • 0 lone pairs
    • 180 degree bond angle

    OR

    3 lone pairs

    OR 

    4 lone pairs
    • Trigonal Planar
    • 0 lone pairs
    • 120 degree bond angle
    • Tetrahedral
    • 0 lone pairs
    • 109 degree bond angle
    • Trigonal Bipyramid
    • 0 lone pairs
    • 120 degree bond angle on horizontal plane
    • 90 degree bond angle on vertical plane
    • Octahedral
    • 0 lone pairs
    • 90 degree bond angle
    • Bent or angular
    • 1 lone pairs
    • 120 degree bond angle

    OR

    • 2 lone pairs
    • 109 degree bond angle
    • Trigonal Pyramid
    • 1 lone pairs
    • 109 degree bond angle
    • Sawhorse or SeeSaw
    • 1 lone pairs
    • 120 degree bond angle on horizontal plane
    • 90 degree bond angle on vertical plane
    • Square Pyramid
    • 1 lone pairs
    • 90 degree bond angle
    • T Shape
    • 2 lone pairs
    • 90 degree bond angle

    OR 

    3 lone pairs
    • Square Planar
    • 2 lone pairs
    • 90 degree bond angle
  27. Polar Bond
    One end of the bond is relatively negative and the other end is relatively positive (i.e. there is a negative pole and a positive pole).
  28. Alcohol
  29. Thiol
  30. Sulfide
  31. Sulfide
  32. Nitro
  33. Ketone
  34. Nitrile
  35. Ether
  36. Ester
  37. Disulfide
  38. Acid Chloride
  39. Alkane
  40. Alkyne
  41. Amine
  42. Alkene
  43. Carboxylic Acid
  44. Imine
  45. Arene
  46. Alkyl Halide
  47. Anhydride
  48. Amide
  49. Wolff-Kishner reaction
    reduces ketones to alkanes with NH2OH then KOH
  50. Gilman reagent
    R2CuLi + RCOCl (creates ketones from chlorides)
  51. anion
    Negatively charged atom
  52. cation
    Positively charged atom
  53. bond length
    The distance between two bonded atoms
  54. bond energy
    The amount of energy needed to split bonded atoms
  55. hydrocarbon
    Compounds with just carbon and hydrogen atoms
  56. isomer
    Molecules with the same kinds and numbers of atoms in different structural orders
  57. Alkenes
    -ene
  58. Alcohols
    -ol
  59. Ketones
    -one
  60. Esters
    -ate
  61. polar covalent bond
    when two non-identical atoms are bonded, they must have different electronegativities, and will attract the shared electrons to different extents, creating a dipole
  62. valence electrons
    the outermost (most loosely held) electrons
  63. node
    a region of zero electron density separating regions of opposite sign in an orbital.
  64. Notation:
    n-, s-, and t-
    • When it’s used: for short chain alkanes and alcohols.
    • What it means: n- means “normal” –  an unbranched chain with the functional group (if present) on the 1-position. s- means “secondary”, t- means “tert“.
    • Why it’s useful: Just a shorthand way of describing different structural isomers.
    • Notes: n-hexane is another frequently encountered name, which simply represents a linear six-carbon chain. “Hexanes”, which you might see in the lab, refers to a mixture of different (branched) isomers of hexane.(it’s purified by distillation, and the isomers have very similar boiling points, so it’s sold as “hexanes”. Pure n-hexane is more expensive because separating it from its isomers is a royal pain).
  65. Notation:
    The N- prefix
    • When it’s used: for amines and amides.
    • What it means: The N- signifies that the substitutent is connected to the nitrogen.Example: N-methyl butylamine, N,N-dimethylformamide.
    • Why it’s useful: it removes ambiguity. “Methyl butylamine”, for instance, could refer to an isomer where the methyl group is on the carbon chain.
    • Notes; when different substituents are present on the nitrogen, the terminology is N-(substituent),N-(substituent), for instance N-methyl,N-ethylbutylamine.
  66. Notation:
    L and D
    • When it’s used: for sugars and amino acids.
    • What it means: It goes back to Emil Fischer, who designated the two enantiomers of glyceraldehyde (the simplest sugar) L-glyceraldehyde and D-glyceraldehyde. At a time (1890) where techniques for determining absolute structure were not available,  he GUESSED(!) that structure of the leveratory (left-rotating) and dextrarotatory (right-rotating) structures of glyceraldehyde was as depicted in the Fischer projection, and gave them the prefixes L and D respectively. Thankfully, when X-ray crystallography was developed, it was found that his guess was correct.   In L-sugars, the oxygen on the  carbon second from the end is on the left hand side in the Fischer projection. In D-sugars, the oxygen is on the right-hand side.
    • Why it’s useful: It was originally used to correlate the absolute structures of sugars to the two glyceraldehydes. It is no longer useful for this purpose, but like the appendix, it hangs around anyway. Like the  appendix, it only seems to get noticed when it causes problems.
    • Notes: This notation causes a lot of confusion. Just because something is “D” does not mean it rotates polarized light to the right and vice versa [that is the function of (+)- and (–)]. For example D-fructose rotates polarized light to the left (–). Furthermore, any correlation between L/D and S/R is coincidental. The 20 essential amino acids in the body are L-amino acids. They are all (S) except for cysteine, which is (R) (due to the sulfur having higher priority in the Cahn-Ingold-Prelog rules). Racemates are written as DL (for instance, DL-glucose is the racemic mixture).
  67. 1 carbon chain
    methane
  68. 2 Carbons chain
    ethane
  69. 3 Carbons chain
    propane
  70. 4 Carbons chain
    butane
  71. 5 carbons chain
    pentane
  72. 6 carbons chain
    hexane
  73. 7 carbons chain
    heptane
  74. 8 carbons chain
    octane
  75. 9 carbons chain
    nonane
  76. 10 carbons chain
    decane
  77. chiral carbon atom
    a carbon atom that is bonded to four different groups
  78. conformers
    structures that differ only by rotations about single bonds. in most cases, conformers interconvert at room temperature; thus, they are not different compounds and not true isomers
  79. diastereomers
    stereoisomers that are not mirror images
  80. enantiomers
    a pair of nonsuperimposable mirror image molecules: mirror image isomers
  81. sigma plane
    a plane of symmetry through the middle of a molecule, dividing the molecule in to two mirror image halves. a molecule containing this plane cannot be chiral.
  82. Wash
    Washing the product of unwanted impurities
  83. Separatory funnel (2)
    • used to separate solvents based on their relative densities
    • the denser solvent is always drained first
  84. Extraction (3)
    • transfer of a dissolved compound from a starting solvent into a solvent in which the product is more soluble
    • like dissolves like
    • use separatory funnel
  85. Filtration (4)
    • isolates solid from liquid using paper filter
    • solid is the residue
    • liquid is the filtrate
    • 2 types: gravity and vacuum filtration
  86. Gravity filtration (3)
    • solvent's own weight pulls it through the filter
    • solvent is desired product
    • use hot solvent
  87. Vacuum filtration (3)
    • solvent forced through filter by a vacuum
    • solid is desired product
    • use Buchner flask
  88. Z isomer
    an isomer having the higher-priority groups on the same side of the double bond
  89. E isomer
    an isomer having the higher-priority groups on opposite sides of the double bond
  90. diene
    a compound with two carbon-carbon double bonds
  91. triene
    a compound with three carbon-carbon double bonds
  92. tetraene
    a compound with four carbon-carbon double bonds
  93. Heisenberg Uncertainty Principle
    you can never determine exactly where an electron is, can only approximate
  94. Hund's rule
    when there are two or more unfilled orbitals electron will go in different ones
  95. most electronegative atom
    Flourine
  96. larger size makes acidity... (stronger or weaker?)
    stronger
  97. more electro negative makes acid...(stronger or weaker?)
    stronger
  98. lewis bases
    species with available electrons to make a bond
  99. lewis acid
    species that can accept a pair of electrons to make a bond
  100. lewis acid synonym
    electrophile
  101. lewis base synonym
    nucleophile
  102. Bronsted-Lowry acid
    any species that can donate a proton
  103. Bronsted-Lowry base
    any species that can accept a proton
  104. anti addition
    a reaction in which two groups add to opposite faces of the double bond
  105. syn addition
    a reaction in which two groups add to the same face of a double bond
  106. Markovnikovs rule
    when a proton acid adds to the double bond of an alkene, the proton bonds to the carbon atom that already has the most hydrogen atoms. in an electrophilic addition to an alkene, the electrophile adds in such a way that generates the most stable intermediate
  107. If you saw a molecular formula indicating between 1 & 4 carbon atoms, what physical state would you expect the molecule to be in at room temperature
    Gas
  108. If you saw a molecular formula indicating between 5 & 17 carbon atoms, what physical state would you expect the molecule to be in at room temperature
    Liquid
  109. If you saw a molecular formula indicating 18 or more carbon atoms, what physical state would you expect the molecule to be in at room temperature
    Solid
  110. How many valence electrons does Carbon have?
    4
  111. When you hear that a hydrocarbon is unsaturated, what do you know about it?
    It must have some double or triple bonds and thus is not bonded to as many hydrogens as possible
  112. When you hear a hydrocarbon is saturated, what do you know about it
    It has only single bonds and is bonded to as many hydrogens as possible.
  113. Define Isomerism
    The possession by two or more distinct compounds of the same molecular formula, each molecule having the same number of atoms of each element, but in different arrangement
  114. Define allotropism
    The existence of an element in two or distinct forms; diamond and graphite
  115. Meta
  116. Ortho
  117. Para
  118. What is the difference between keytones and aldehydes
    Where the double Oxygen bond is placed
  119. Are Keytones and isomere of aldehydes? Why or why not
    No, they have different numbers of hydrogens
  120. What type chemical do you get if you oxidize a secondary alcohol
    ketone
  121. What is the street name of acetic acid
    Vinegar
  122. What type chemical do you get if you oxidize a primary alcohol
    Aldehyde
  123. zwitter ion
    an ion with both + and - charges in same ion
  124. dehydration
    the elimination of a molecule of water from an alcohol. OH is removed from one carbon and H is removed from the other
  125. hydrogen bonding
    the intermolecular force in which a hydrogen atom that is bonded to a highly electronegative atom is attracted to an unshared pair of electrons of an electronegative atom in a nearby molecule
  126. diol
    any of a class of alcohols having 2 hydroxyl groups in each molecule
  127. triol
    any of a class of alcohols having 3 hydroxyl groups in each molecule
  128. As a substituent, an aromatic ring is called either a ___ or a ___ group
    phenyl, aryl
  129. Aniline
  130. Benzene
  131. Benzoic Acid
  132. Toluene
  133. Nitrobenzene
  134. Phenol
  135. X₂/FeX₂
    Halogenation
  136. HNO₃/H₂SO₄
    Nitration
  137. SO₃/H₂SO₄
    Sulfonation
  138. RCl/AlCl₃
    Alkylation
  139. RCOCL/AlCl₃
    Acylation
  140. KMnO₄
    Oxidation
  141. H₂/Pd
    Reduction of Substituent to Single Bonds
  142. H₂, Pt/2000 psi
    Reduction of Ring and Substituent to Single Bonds
  143. Zn(Hg), HCl
    or
    NH₂ NH₂ + OH-
    Reduction to Alkyl
  144. Pd/H₂
    or
    Fe/HCL
    or
    Sn/ HCL
    Reduction to Aniline
  145. Hydrogen Valence Electrons
  146. Lithium Valence Electrons
  147. Sodium Valence Electrons
  148. Helium Valence Electrons
  149. Argon Valence Electrons
  150. Carbon Valence Electrons
  151. Nitrogen Valence Electrons
  152. Oxygen Valence Electrons
  153. Sulfer Valence Electrons
  154. Cloride Valence Electrons
  155. Aluminum Valence Electrons
  156. Magnesium Valence Electrons
  157. Fluorine

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