Organic Chem Test 1

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  1. Which of the following molecules would you expect to have a dipole moment of 0?
    a) CH3CH3 
    b) CHCl3 
    c) N(CH3)3 
    d) HCOOH
    e) H2C=CH2
    a and e
  2. Predict the bond angles for the following:
    C-N-H in (CH3)2NH
    angle ~109.5
  3. Predict the bond angles for the following:
    C-N-C in (CH3)2NH
    angle ~109.5
  4. Predict the bond angles for the following:
    C-O-C in CH3CH2OCH3
    angle ~109.5
  5. Predict the bond angles for the following:
    H-C-H in H2C=O
    angle ~120
  6. Indicate the hybridization for the following carbon atoms:
    Image Upload
    • sp3: a,c,d
    • sp2: b
    • sp:  e
  7. Give the functional groups:
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    • Amide
    • Ketone
    • Ether
    • Ester
    • Alcohol
  8. Definition: covalent bond
    the sharing of electron pairs between atoms
  9. Heisenberg Uncertainty Principle
    It is not possible to determine both the position and the momentum of an electron
  10. Probability Dirtribution
    Probability of finding an electron in any region around a nucleus
  11. Hund's Rule
    Every Orbital in a subshell is singly occupied with one electron before any one orbital is doubly occupied, and all electron in singly occupied orbitals have the same spin.
  12. What is Hydrogen's normal bonding pattern?
    Monovalent, single bond no lone pairs.
  13. What is Boron's normal bonding pattern?
    trivalent, no electron pairs
  14. What is Carbon's normal bonding pattern?
    • tetravalent, no electron pairs 
    • Forms 4 bonds and doesn't like to have lone pairs on the loose.
  15. What is Nitrogen's normal bonding pattern?
    • Trivalent with one electron pair.
    • 3 bonds and a set of lone pair electrons
  16. What is Oxygen's normal bonding pattern?
    • divalent with 2 electron pairs.
    • two bonds, with two sets of lone pair electrons.
  17. What is Halide's normal bonding pattern?
    • monovalent, with 3 electron pairs.
    • 1 bond, with 3 electron pairs.
  18. Formal Charge
    • Is the chare on an atom in a molecule or ion based on a prescribed procedure for counting which electrons may be assigned to each individual atom.
    • FC= # of valence electron in neutral atom - (All unshared electrons + 1/2 of all shared electrons)

    note that the negative charge of a molecule belongs to the most electronegative element.
  19. Image Upload
    • Tetrahedral
    • 109 degree bond angle

    We have 4 orbitals of sp3 of identical energy (somewhere between the 2s and 2p orbitals)

    --Ë--

    >Ë--

    >Ë<
  20. Image Upload
    • Trigonal Planar
    • 120 degree bond angle

    =Y<

    =Ÿ--

    --Ÿ<

    =Ÿ:
  21. Image Upload
    • Linear
    • 180 degree bond angle

    • =z-
    • =z=
    • =z:
  22. Why do Hybrid Orbitals form?
    Ultimately it is a way to lower energy.

    • 1. Electron pair repulsions are minimized
    • 2. Stronger bonds are formed
    • 3. Hybrids have better directionality for forming bonds
    • 4. Since promotion usually occurs, hybrids allow more bonds to form
  23. Sigma bonds
    Shorter=Stronger=more S Character

    You can rotate freely around a sigma bond

    • sp3
    • the first bond of a sp2 and sp
  24. Arrange in order of increasing acidity:
    1) sulfuric acid          SO3H
    2) hydrobromic acid   H-Br
    3) Carboxcylic Acid    COOH
    4) Hydronium ion      H3O+
    5) Hydrofluoric Acid   H-F
    6) hydroiodic acid     H-I
    7) Sulfonic acids       H2SO4
    8) hydrochloric acid   H-Cl
    • 3) Carboxcylic Acid
    • 5) Hydrofluoric Acid
    • 7) Sulfonic acids
    • 4) Hudronium ion
    • 1) sulfuric acid
    • 8) hydrochloric acid
    • 2) hydrobromic acid
    • 6) hydroiodic acid
  25. Arrange in order of increasing acidity:
    1) pronated amines
    2) Water
    3) Dialdehyde
    4) Alcohol
    5) carboxcylic acids
    6) thiols
    • 4) Alcohol
    • 2) Water
    • 3) Dialdehyde
    • 6) thiols
    • 1) pronated amines
    • 5) carboxcylic acids
  26. Arrange in order of increasing acidity:
    1) Alcohol
    2) Alkyne
    3) Water
    4) Nitrile
    5) Ketone / Aldehyde
    6) Ester
    • 2) Alkyne
    • 6) Ester
    • 4) Nitrile
    • 5) Ketone / Aldehyde
    • 1) Alcohol
    • 3) Water
  27. Arrange in order of increasing acidity:
    1) Alkene
    2) Sulfoxide
    3) Alkyne
    4) Hydrogen
    5) Alkane
    6) Amine
    • 5) Alkane
    • 1) Alkene
    • 4) Hydrogen
    • 6) Amine
    • 2) Sulfoxide
    • 3) Alkyne
  28. Acid is a proton _______
    • donor
    • lacks electrons, has a new positive charge
  29. A base is a proton _______
    acceptor
  30. pKa
    Stonger acid's a have a more negative number, weaker acids have a higher number
  31. Factors that Increase Acidity
    • Stabilization of conjugate bases:
    • 1) Resonance: more resonance structures or better resonance structures for the conjugate base lead to a stronger acid
    • 2) Electronegativity: allows better handling of negative charge (when comparing two elements in the dame period)
    • 3) Size of atoms: larger molecules have more surface to deal with the negative charge
    • 4) Hybridization: more s character in the orbital bearing the negative charge in the conjugate base leads to a stronger acid
    • 5) Inductive effects: neighboring atoms help deal with the charge
    • 6) Charge
    • 7) solvation: Stronger acid has higher solvation
    • 8) Steric effects
  32. The conjugate acid of a weak base will be a ___________
    strong acid
  33. The conjugate acid of a strong base will be a __________
    weak acid
  34. Acid-Base Reaction
    A reaction in which an acid donates a proton to a base
  35. Acidity
    A measure of how easily a compound gives up a proton
  36. Antibonding molecular orbital
    a molecular orbital that results when two atomic orbitals with opposite phases interact.  Electron in an antibonding orbital decrease the bond strength
  37. Atomic Number
    tells how many protons (or electrons) the neutral atom has
  38. Atomic Orbital
    an orbital associated with an atom; the three dimensional area around a nucleus where electrons are most likely to be foung
  39. Atomic Weight
    the average mass of the atoms in the naturally occurring element
  40. Aufbau principle
    states that an electron will always go into the available orbital with the lowest energy
  41. Basicity
    describes the tendency of a compound to share its electron with a proton
  42. Acidity
    A measure of how easily a compound gives up a proton
  43. Bond Dissociation energy
    The amount of energy required to break a bond in a way that allows each of the atoms to retain one of the bonding electrons, or the amount of energy released when a bond is formed
  44. Bonding Molecular Orbital
    A molecular orbital that results when two atomic orbitals with the same phase interact.  Electrons in a bonding orbital increase bond strength
  45. Bond Length
    the internuclear distance between two atoms at minimum energy (maximum stability)
  46. Buffer solution
    solution of a weak acid and its conjugate base
  47. Carbanion
    A species containing a negatively charged carbon
  48. Carbocation
    a species containing a positively charged carbon
  49. Condensed Structure
    A structure that does not show some (or all) if the covalent bonds
  50. Core electrons
    electrons in filled shells
  51. Covalent Bond
    a bond created as a result of sharing electrons.
  52. Degenerate orbitals
    orbitals that have the same energy
  53. Delocalized Electrons
    electrons that do not belong to a single atom nor are they shared in a bond between two atoms
  54. Dipole
    A separation of positive and negative charges
  55. Electronegative
    Describes an element that readily acquires an electron
  56. Electronegativity
    • the tendency of an atom to pull electrons toward itself
    • F is most electronegative
  57. Electropositive
    Describes an element that readily loses an electron
  58. Electrostatic Attraction
    an attractive force between opposite charges
  59. Equilibrium Constant
    the ratio of products to reactant at equilibrium
  60. Free Radical
    A species with an unpaired electron
  61. Hybrid Orbital
    an orbital formed by hybridizing (mixing) atomic orbitals
  62. Hydride ion
    a negatively charged hydrogen (a hydrogen atom with an extra electron)
  63. Hydrogen Ion
    a positively charged hydrogen (a hydrogen atom without its electron)
  64. Inductive Electron Withdrawal
    the pull of electrons through sigma bonds by an atom or a group of atoms
  65. Ionic Bond
    a bond formed as a result of the attraction of opposite charges
  66. Ionic Compound
    A compound composed of a positive ion and negative ion
  67. Ionization Energy
    The energy required to remove an electron from an atom
  68. Isotopes
    atoms with the same number of protons but a different number of neutrons
  69. Kekule structure
    a model that represents the bonds between atoms as lines
  70. Lewis Structure
    a model that represents the bonds between atoms as lines or dots and the lone pair electrons as dots
  71. Lone-Pair Electrons
    valence electrons not used in bonding
  72. Mass Number
    the number of protons plus the number of neutrons in an atom
  73. Molecular Orbital
    an orbital associated with a molecule that results from the combination of atomic orbitals
  74. Non Polar Covalent Bond
    a bond formed between two atoms that share the bonding electrons equally
  75. Organic Compound
    A compound that contains carbon
  76. pH
    the scale is used to describe the acidity of a solution (pH= -log[H+])
  77. Polar Covalent Bond
    a bond formed between two atoms that do not share the bonding electrons equally
  78. pKa
    describes the tendency of a compound to loose an proton (pKa = -log Ka)
  79. Proton
    A positively charged Hydrogen ion
  80. Proton Transfer REaction
    a reaction in which a proton is transferred from an acid to a base
  81. Resonance
    Having delocalized electrons
  82. Resonance Contributers
    structures with localized electrons that together approximate the true structure of a compound with delocalized electrons
  83. Resonance Hybrid
    The actual structure of a compound with delocalized electrons
  84. Image Upload
    Alcohol
  85. Image Upload
    Alkane
  86. Image Upload
    Alkene
  87. Image Upload
    Alkyl Halide
  88. Alkyl Substituent
    A substituent formed by removing a hydrogen from an alkane
  89. Image Upload
    Amine
  90. Image Upload
    Amide
  91. Angle Strain
    the strain introduced into a molecule as a result of its bond angles being distorted from their ideal values.
  92. Anti Conformer
    The staggered conformer in which the larges substituents bonded to the two carbons are opposite each other.  It is the most stable of the staggered conformers.
  93. Axial bond
    a bond of the chair conformer of cyclohexane that is perpendicular to the pane in which the chair is drawn (an up-down bond)
  94. Banana Bonds
    the bonds in small rings that are slightly bent as a result of orbitals overlapping at an angle rather than overlapping head on
  95. Boat conformer
    the conformer of cylclohexane that roughly resembles a boat
  96. Chair conformer
    the conformer of cylclohexane that roughly resembles a chair.  It is the most stable conformation of cyclohexane
  97. Constitutional Isomers
    Molecules that have the same molecular formula but differ in the way the atoms are connected
  98. 1,3 diaxial Interaction
    an interaction between an axial substituent and the other two axial substituents on the same side of a cyclohexane ring
  99. eclipsed conformer
    a conformer in which the bonds on adjacent carbons are parallel to each other when viewed looking down the carbon-carbon bond
  100. Equatorial Bond
    a bond of the chair conformer of cyclohexane that juts out from the ring in approximately the same plane that contains the six ring carbon atoms
  101. Image Upload
    Ether
  102. Flagpole Hydrogens
    The two hydrogens in the boat conformer of cyclohexane that are closest to each other; they are at the 1 and 4 positions of the ring
  103. Gauche Conformer
    the staggered conformer in which the larges substituents bonded to the two carbons are gauche to each other (approximately 60 degrees apart)
  104. Gauche interaction
    the interaction between two atoms or groups that are gauche to each other
  105. Half Chair Conformer
    • aka envelope
    • the lease stable conformer of cylclhexane
  106. Homologous Series
    a family of compounds in which each member differs from the next one by one methylene group
  107. Hydrocarbon
    a compound that contains only carbon and hydrogen
  108. Hydrogen Bond
    an unusually strong dipole-dipole attraction between a hydrogen bonded to O, N, or F and the lone pair of a different O, N, or F
  109. Induced Dipole-Induced Dipole Interaction
    an interaction between a temporary dipole in one molecule and the dipole that the temporary dipole induces in another molecule
  110. Methylene Group
    CH2 group
  111. Newman Projection
    a way to represent the 3-dimensional spatial relationships of atoms by looking down the length of a particular carbon carbon bond
  112. Polarizability
    the ease with which an electron cloud of an atom can be distorted
  113. Primary Alcohol
    an alcohol in which the OH group is bonded to a primary carbon
  114. Primary amine
    an amine with one alkyl group bonded to the nitrogen
  115. Quaternary ammonium salt
    a nitrogen compound with four alkyl groups bonded to the nitrogen plus a negatively charged counter ion
  116. Ring Flip
    • Chair Chair conversion
    • the conversion of a chair conformer of cyclohexane into the other chair conformer.  Bonds that are axial in one chair conformer are equatorial in the other.
  117. Secondary Alcohol
    an alcohol in which the OH group is bonded to a secondary carbon
  118. Solubility
    the extent to which a compound dissolves in a solvnet
  119. Solvation
    the interaction between a solvent and another molecule or ion
  120. Steric Strain
    the repulsion between the electron cloud of an atom or group of atoms and the electron cloud of another
  121. Structural Isomers
    • aka Constitutional Isomers
    • molecules that have the same molecular formula but differ in the way the atoms are connected
  122. Image Upload
    symmetrical ether
  123. Van Der Waals Forced
    Induced Dipole Induced Dipole interacitons
Author:
bnpusey
ID:
233820
Card Set:
Organic Chem Test 1
Updated:
2013-09-23 19:53:14
Tags:
Organic Chemistry Structure Bonding Compounds Acidity
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All I need for Exam 1
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