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  1. Enantiomers
    Mirror Image isomer, pair of compounds that are nonsuperimposible
  2. Achiral
    An object that is superimposable (identical) to its mirror image.
  3. Diastereomer
    Stereoisomers that are not enantiomers
  4. Meso Compound
    A comund that has multiple but is achiral due to an internal plane of symmetry
  5. Stereocenter
    Stereogenic center, Asymmetrical carbon atom (w/ four different substiuents)
  6. If a compund is chiral it must have....
    an enantiomer
  7. If a compund has no asymetrical carbons it is...
    achiral
  8. If a compound has only one asymmetrical carbon atom, it is...
    Chiral
  9. If a compound has more than one asymmetrical carbon atom, the compound is..
    chiral or achiral, it depends.
  10. When taking mirror images of CH3 and NH2, they turn into...
    H3C and H2N
  11. Any molecule that has an internal mirror plane of symmetry cannot be ______, even though it may contain asymmetric carbons.
    chiral
  12. A carbon with only 3 different substiuents has...
    an internal mirror plane
  13. Asymmetrical carbon atoma are always
    nonsuperimposable
  14. Racemic mixture...
    A sloution has equal amounts of (+) and (-) solutions so it can be optically inactive. (rotation of 0o)
  15. How do you find the Opitcal Purity?
    divide the observed rotation by the rotation of the pure enantiomer and multiply by 100%
  16. What is the enantomeric excess ?
    the optical purity (d-l)/(d+l)
  17. Optically active is...
    chirality
  18. Allenes have two....
    double bonds
  19. If the mirror image of a compound is the original compound rotated by 180o it is..
    the same thing
  20. If the mirror image of a compound is the original compound rotated by 90o it is..
    an enantiomer
  21. In a fischer projection, if the gropus are changed around an odd number of times, it is...
    enantiomeric
  22. In a fischer projection, if the gropus are changed around an even number of times, it is...
    the same thing
  23. Molecules with symmetry planes cannot be ...
    chiral
  24. In a fischer projection, To figure out if the mirror image of a compound in an enantiomer...
    rotate the mirror image by 180o and if it does not match the original image, it is an enantiomer.
  25. In the fischer projection with one asymmetric carbon, the atom postions in correlation with the perspection drawing from "left" to "up" to "right" to "bottom" are....
    • Wedge, Top, Plane, Dash
    • "Willie Tells Patty's Details"
  26. In the fischer projection with two asymmetric carbons, the atom postions in correlation with the perspection drawing from "topleft" to "top" to "topright" to "bottomright" to "bottom" to "bottom left" are....
    • Left Wedge, Left Plane, Left Dash, Right Dash, Right Plane, Right Wedge
    • "Will pleases Ducks, Ducks please Will"
  27. Alkyl Halide is an...
    halogen atom bonded to one sp3 hybrid carbons atom of an alkyl group
  28. A vinyl halide is...
    Halogen atom bonded to one of the sp2 hybrid carbon atom of an alkene
  29. An aryl halide is..
    halogen atom bonded to one of the sp2 hybrid carbon atoms of an aromatic ring. (Three double bonds in it)
  30. An sp3 hybrid carbon has ____ sigma bonds.
    four
  31. An sp2 hybrid carbon has ____ sigma bonds.
    three
  32. An sp hybrid carbon has ____ sigma bonds.
    two
  33. What is the IUPAC nomeclature template for an alkyl halide?
    • Haloalkane
    • Halogen + Alkane (Bromo-propane)
  34. What is the trival/common nomeclature template for an alkyl halide?
    • Alkylhalide
    • Alkyl + Halide (Isopropyl Bromide)
  35. CH2X2 is a...
    Methylene Halogen
  36. CHX3 is a...
    Haloform
  37. CX4 is a...
    Carbon Tetrahalide
  38. If a halogen carbon atom is bonded to one carbon atom it is a ...
    Primary Halide = 1o
  39. If a halogen carbon atom is bonded to two carbon atoms it is a ...
    Secondary Halide = 2o
  40. If a halogen carbon atom is bonded to three carbon atoms it is a ...
    Tertiary Halide = 3o
  41. If a halogen carbon atom is bonded to no carbon atoms it is a ...
    methylhalide
  42. Geminal dihalide is a...
    two halogen atoms bonded to some carbon
  43. Vicinal dihalide is a ...
    Two halogen atoms bonded to adjacent carbon atoms
  44. Halogen is always more _____ than carbon
    electronegative
  45. The dipole of CX4 is always...
    0
  46. The strongest attraction in akyl halides is..
    London forces
  47. In alkyl halides, the larger the surface area, the _____ the attraction.
    Stronger
  48. In alkyl halides, the stronger the attraction, the _____ the boiling point...
    Higher
  49. In alkyl halides, Dipole-Dipole attractions affect the boiling point at a _____ extent.
    smaller.
  50. Higher molecular weight = ______ boiling point
    higher
  51. Branched and spherical compounds have a _____ boiling point.
    lower
  52. Alkyl bromides/iodides are ______ than water.
    Denser
  53. Alkyl chlorides are ______ than water.
    less dense
  54. Alkyl fluorides are ______ than water.
    less dense
  55. Alkyl chlorides (2 or more cl atoms) are ______ than water.
    denser
  56. Allylic position is...
    A carbon atom next to a carbon-carbon double bond
  57. Intermediates are...
    cations, radicals, anions (stabilized by ressonance w/ double bonds) = charge/radical delocalized
  58. What is allylic bromination?
    When Br2 takes an allylic hydrogen atom to leave a resonance-stablilized allylic radical. The radical then reacts with Br2 to regenerate a Bromine radical that continues a chain reaction.
  59. List the steps of allylic bromination.
    • Bromine absorbs light, causing formation of radicals.
    • A bromine radical abstracts an allylic hydrogen. (Leaving an allylic radical and HBr)
    • Either radical carbon can react with bromine. (Leaving an allylic bromide (and a possible allylic shift) and a bromide ion- )
  60. When something replaces the halogen ion it is .....
    substiution
  61. When the halide ion leaves with another atom is ....
    elimination
  62. dehydrohalogenation is a kind of...
    elimination
  63. in eliminations, a lost of H--X from alkyl halide gives...
    an alkene.
  64. When a elimination occurs, a ______ is formed.
    Pi bond
  65. The general nucleophilic substituion form...
    Nucleophile + Substrate ---> Product & Leaving Group
  66. A donor on an electron pair is...
    a nucleophile
  67. Something is electrophillic when it...
    the atom isbonded to an electronegative atom.
  68. Carbons will have a partial positive charge because of...
    Halogen's electronegativity
  69. Nucleophiles always attack....
    Electrophiles
  70. The SN2 reaction is _____ order.
    Second
  71. SN2 has no....
    intermediates
  72. How many steps does SN2 have?
    one
  73. What is the order of reactivity for substrates in the SN2 reaction?
    CH3 > 1o > 2o >> 3o
  74. OR' is....
    an ether
  75. OH is an...
    alcohol
  76. R' - COO - R is a....
    Ester
  77. Halides can be turned into halides by....
    Halogen exchnage reactions (flip flopping halogens)
  78. When F wants to be a nucleophile what happens?
    It can't do it alone, needs a helper (KF/18-Crown-6)
  79. If a atom forms a new bond to a proton it's a...
    base
  80. If a atom forms a new bond to a carbon it's a ....
    nucleophile
  81. On the P Table, nucleophilicity decreases....
    From left right
  82. On the P table nucleophilicity increams from
    top to bottom
  83. As Polarizability increases, nucleophilicity....
    increases
  84. As electronegativity increases, nucleophilicty ....
    decreases
  85. If an atom is "soft" it's
    Highly polarizable
  86. If an atom is "hard" it's
    Lowly polarizable
  87. Steric Hinderance...
    When bulky groups interfere with a reaction by virtue of their size.
  88. If you want a base use ...
    A bulky reagent
  89. If you want a nucleophile use...
    less hindered reagent.
  90. Protic slovent...
    acidic protons usually in the form of O-H or N-H to attach to nucleophiles
  91. Small anion _____ nucleophilicity because?
    • reduced
    • More energy needed to strip off slovent from solvated ion
  92. Large anion _____ nucleophilicity because?
    • increased
    • Less energy used to strip off solvents
  93. OR is used to...
    solvate
  94. aprotic solvents
    solvents with or w/o O-H or N-H (enhances nucleophilicty of anions
  95. Why is an anion more reactive in a aprotic solvent?
    Not strongly solvated
  96. Most polar ionic reagents are insoluble in....
    simple aprotic solvents
  97. Polar aprotic solvents
    strong dipole moments to enhancesolubility (even though no N-H or O-H bonds)
  98. In an SN2 reaction, the leaving group's purposes are
    • polarize the C-X bond (making carbon electrophile)
    • Leaves w/ the pair of electrons that once bonded it to the electrophilic atom.
  99. A good leaving group has to be...
    stable and electron withdrawing (polarize carbon)
  100. Carbon needs to be partially positive to be ...
    electrophillic
  101. OH is a _____ leaving group
    poor
  102. A nucleophillic attack on a primary halide is...
    easy because unhindered
  103. A nucleophillic attack on a secondary halide is...
    Possible but hindered
  104. A nucleophillic attack on a tertiary halide is...
    Impossible....too bulky
  105. A neutral molecule can serve as a leaving group from a ......
    positively charged species
  106. In SN2, the nucleophile does a _______ attack
    back-side
  107. Solvolysis...
    When solvent is nucleophile
  108. SN1 reaction rate is ____ order
    First
  109. List the steps of the SN1 Mechanism..
    • 1. Carbocation forms (ionization- rate limiting)
    • 2. Nucleophile attacks the carbocation
    • 3. Proton is loss to slovent
  110. What is the reactivity for SN1?
    3o > 2o > 1o > CH3X
  111. _______ groups enhance the SN1 Reaction...
    alkyl
  112. Vinyl and Aryl groups do not undergo ______ reactions.
    SN1 and SN2
  113. Why can't vinyl or aryl groups undergo an SN1 reaction?
    Can't ionize because they are so weak
  114. Why can't vinyl or aryl groups undergo an SN2 reaction?
    Cannot be attacked, too bulky.
  115. For good ion stabilization use a ____ solvent
    polar
  116. When carbon and the leaving group are being solvated, who gets the oxygen and who gets the hydro?
    • Carbon = Oxygen
    • Leaving group = Hydro
  117. Carbocation is...
    intermediate that is sp2 hybridized and planar
  118. Retention of configuration happens in...
    SN1
  119. Retention of configuration happens when...
    Nucleophile attacks from the side the leaving group left from.
  120. Inversion of configuration happens when ...
    Nucleophile attack from the back side
  121. What are the steps of racemization in the SN1 reaction?
    • 1. Ionization for carbocation
    • 2. Nucleophile can attack from bottom or top ( if on top = retention of configuration, if on bottom = inversion of configuartion)
  122. Will you find rearrangments in SN1?
    Yes
  123. Will you find rearrangments in SN2?
    No
  124. Why is there no rearrangemtns in SN2?
    You need a carbocation to rearrange something...SN2 is a one step reaction with no carbocation.
  125. Rearrangments result from a ...
    hydride shift
  126. List the steps of hydride shift in SN1...
    • 1. Ionization for a carbon cation
    • 2. Shift hydrogen to the carbocation for stability and get a higher degree of carbocation (perferably tertiary)
    • 3. Have a solvent attack the new carboncation
    • 4. Deprotonize the compound with another molecule of the solvent to leave the new compound with a proton loss and a new solvent moleclue with a proton gain.
  127. List the steps of the E1 reaction...
    • 1. Ionize (rate-limiting step) to get a carbocation
    • 2. Weak base comes and deprotonates the compound
    • 3. With empty oribtals, Carbon bonds are forced to form a double bond to compensate the lost of the leaving group and proton, forming an alkene and the protonated base and negative leaving group.
  128. Dehydrohalogenation....
    Loss of a proton and halogen
  129. List the steps of rearrangemnent in the E1 reaction.
    • 1. Ionize to get a carbocation
    • 2. Hydride shift to form a stable carboncation
    • 3. Weak basic solvent removes a proton to make an alkene. Shifting things around can result into multiple compounds witht the bonds in different places.
  130. Zaitev's Rule...
    In Elimination reactions... The most substituted compound, usually predominates because they are the most stable
  131. Explain the steps of the E2 Reaction...
    • 1. Leaving group leaves then..
    • 2.Strongbase/Nucleophile used for a poor SN2 substrate (something usually hindered, 3o or 2o) takes a proton
  132. What is the reactivity for the E2 reaction?
    3o > 2o > 1o
  133. Eclipsed conformation = _____ energy
    higher
  134. Staggered conformation = ___ energy
    less
  135. For E2 the molecule should be .....
    Anti-Coplanar
  136. Is there any rearrangments in E2?
    Nooo
  137. If the base/nucleophile is strong (HO- or RO-) what kind of reaction can it be?
    SN2 or E2 (second order)
  138. If the base/nucleophile is weak (H2O or ROH) what kind of reaction can it be?
    SN1 or E1 (first order)
  139. If the base/nucleophile is strong (HO- or RO-) and the substrate is primary or methyl what reaction is it?
    More SN2 than E2 (E2 can happen w/ higher temperature and a hindered base)
  140. If the base/nucleophile is strong (HO- or RO-) and the substrate is secondary what reaction is it?
    SN2 and E2 (higher temperature and hindered base favor E2)
  141. If the base/nucleophile is strong (HO- or RO-) and the substrate is tertiary what reaction is it?
    E2 (SN2 would be extremely slow)
  142. If the base/nucleophile is weak (H2O or ROH)and the substrate is primary or methyl, what kind of reaction can it be?
    No real reaction. too slow
  143. If the base/nucleophile is weak (H2O or ROH)and the substrate is secondary or tertiary, what kind of reaction can it be?
    SN1 and E1 (higher temperature and hindered base wants elimination)
  144. What is the double bond energy?
    611 kJ/mol
  145. What is the sigma bond energy?
    347 kJ/mol
  146. What is the pi bond energy?
    264 kJ/mol
  147. The more s orbital you have = the _____ bond length
    shorter
  148. How much "s" in sp?
    1/2
  149. How much "s" is in sp2 ?
    1/3
  150. How much "s" is in sp3?
    1/4
  151. What is the elements of unsaturation formula?
    1/2( 2C + 2 - H)
  152. How many elements of unsaturation is a Double bond?
    One
  153. How many elements of unsaturation is a ring?
    One
  154. How many elements of unsaturation is a triple bond?
    two
  155. If an alkene is unsaturated what can you do to it?
    add a hydrogen in a catalystic presence
  156. What is a saturated alkene?
    alkane (cannot react anymore)
  157. When determing count for element of unsaturation, halogens are...
    Hydrogen
  158. When determing count for element of unsaturation, oxygens are...
    ignored
  159. When determing count for element of unsaturation, nitrogens are...
    a half of carbon
  160. Nomenclature of the alkenes are like the alkanes just with ____ on the end
    "ene"
  161. When naming alkenes what the order you should follow?
    Substiuents first then double bond position.
  162. =CH2
    • Methylene
    • (Methyldiene)
  163. -CH=CH2
    • Vinyl
    • (Ethenyl)
  164. -CH2-CH=CH2
    • Allyl
    • (2-Propyl)
  165. If a carbon hold two or more of identical groups, there can be no...
    Cis or trans
  166. In the E-Z system, E is..
    Opposite
  167. In the E-Z system, Z is ...
    the same side
  168. How do you assign E and Z?
    mentally split the alkene into two parts, on the left assign priority to the two substiuents, then on the right assign the priorities, if "1" of the left and "1" of the right, are directly across from each other it is "Z". If they are diagonal from each other they are "E"
  169. To name an alkene by it's common/trival name use..
    • the IUPAC name but "yl" to the end of the alky part
    • (ethYLene, propYLene)
  170. Which are more stable trans or cis?
    trans
  171. Why is trans more stable then cis?
    Because alkyl substiuents and seperated and farther apart in the trans isomer.
  172. Less energy means _____ stability.
    More
  173. Monosubstituted means more ______ and Less _____
    • energy
    • Stability
  174. Tetrasubstituted means more ______ and Less _____
    • Stability
    • Energy
  175. If there is more energy it is less stable, meaning more _______
    reactivity

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