Term
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Definition
| charge associated with an atom that does not exhibit the expected number of valence electrons |
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Term
| the 2 commandments of drawing resonance structures |
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Definition
1: never break a single bond
2: never exceed an octet for second-row elements |
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Term
| the 3 questions that determine whether or not a resonance structure can be drawn |
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Definition
1: Can we convert any lone pairs into pi bonds without breaking the 2 commandments?
2: Can we convert any pi bonds into lone pairs without breaking the 2 commandments?
3: Can we convert any pi bonds into pi bonds without breaking the 2 commandments? |
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Term
| the 5 patterns you should recognize to become proficient at drawing resonance structures |
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Definition
| 1: a lone pair next to a pi bond
2: a lone pair next to C+
3: a pi bond next to C+
4: a pi bond between 2 atoms, where one of those atoms is electronegative
5: pi bonds going all the way around a ring |
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Term
| what a lone pair next to a pi bond means for resonance |
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Definition
you can bring down the lone pair to form a pi bond and kick up the pi bond to form a lone pair
[image] |
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Term
| what a lone pair next to C+ means for resonance |
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Definition
| the lone pair forms a pi bond with that C+ |
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Term
| what a pi bond next to C+ means for resonance |
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Definition
| the pi bond moves such that a new pi bond is formed and another C becomes C+ |
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Term
| what a pi bond between 2 atoms, where one of those atoms is electronegative means for resonance |
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Definition
| the electrons in the pi bond gravitate towards the electronegative element |
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Term
| what pi bonds going all the way around a ring means for resonance |
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Definition
| the pi bonds can move in a circle |
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Term
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Definition
alternating double and single bonds
[image] |
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Term
| the 4 rules of assessing the relative importance of resonance structures |
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Definition
1: OCTET; the most important resonance structures have the greatest number of filled octets and covalent bonds
2: FORMAL CHARGES; the structure with fewer formal charges is more important
3: NEGATIVE CHARGE ON ELECTRONEGATIVE ELEMENT; other things being equal, a structure with a more negative charge on a more electronegative element will be more important
4: LEWIS STRUCTURES; resonance structures that have equally good Lewis structures are described as equivalent and contribute equally to the resonance hybrid |
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Term
| resonance structures to not draw |
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Definition
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Term
| how to determine the willingness of an acid to donate its proton |
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Definition
| by determining the stability of the negative charge on its conjugate base |
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Term
| the 4 important factors of acid-base reactions |
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Definition
1: what atom is the charge on?
2: resonance
3: induction
4: orbitals |
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Term
| periodic trend in electronegativity |
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Definition
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Term
| periodic trend in ability to stabilize a charge (polarizability) |
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Definition
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Term
| how resonance makes a molecule more acidic |
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Definition
| the charge on its conjugate base is spread over a wider area |
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Term
| induction (in the context of acid-base reactions) |
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Definition
| "pulling" of electron density caused by differences in electronegativity |
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Term
| the shapes of sp, sp2, and sp3 orbitals |
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Definition
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Term
| why a proton on a triple bonded carbon is more acidic |
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Definition
| because the lone pair in the conjugate base is held more closely to the nucleus |
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Term
| how closely orbitals hold lone pair electrons to nucleus |
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Definition
| sp more closely than sp2 more closely than sp3 |
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Term
| factors of acid-base rxns in order of importance |
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Definition
atom, resonance, induction, orbital (ARIO)
1: atom the charge is on
2: resonance on conjugate base
3: induction
4: orbital that has the negative charge |
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Term
| important exception to the order of importance of factors in acid-base rxns |
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Definition
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Term
why the conjugate base on the left is more stable than the conjugate base on the right
[image] |
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Definition
| because a negative charge on an sp hybridized carbon is more stable than a negative charge on an sp3 hybridized nitrogen |
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Term
| another factor that can affect the stability of conjugate bases |
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Definition
| interactions with solvent (solvating effect) |
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Term
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Definition
| greater steric bulk around atom with negative charge makes corresponding conjugate acid less acidic |
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Term
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Definition
| lower pKa means more acidic |
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Term
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Definition
logarithmic
example: pH 3 is 10 times more acidic than pH 4 |
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Term
| which side of an acid-base rxn is favored when at equilibrium? |
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Definition
| the side that has the more stable negative charge |
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Term
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Definition
| if the geometry of molecules prevents them from getting close, then there can'e be a rxn |
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Term
| how covalent bonds are formed |
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Definition
| by the overlapping of orbitals |
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Term
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Definition
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Term
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Definition
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Term
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Definition
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Term
| bond angle for tetrahedral (sp3 hybridized) |
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Definition
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Term
| bond angle for trigonal planar (sp2 hybridized) |
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Definition
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Term
| bond angle for linear (sp hybridized) |
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Definition
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Term
| the 5 parts to naming organic molecules |
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Definition
1: stereoisomerism
2: substituents
3: parent
4: unsaturation
5: functional group |
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Term
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Definition
| indicates stereocenters (R, S) and whether double bonds are cis/trans |
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Term
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Definition
| groups connected to the main chain |
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Term
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Definition
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Term
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Definition
| identifies if there are any double or triple bonds |
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Term
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Definition
| the group after which the compound is named |
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Term
| some elements that gent named as substituents instead of functional groups |
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Definition
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Term
| when a compound has double and triple bonds, which bonds get listed first? |
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Definition
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Term
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Definition
ring
this is te prefix for carbon atoms in a ring |
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Term
| the functional group that needs to be connected to the parent chain |
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Definition
| the functional group with higher priority |
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Term
| the carbon chain that has to be the parent chain |
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Definition
| the one with the double or triple bond, if there is one |
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Term
| hierarchy when finding the parent chain |
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Definition
1: functional group
2: double bond
3: triple bond |
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Term
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Definition
| isomers that differ in spatial orientation |
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Term
| hierarchy when numbering the parent chain |
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Definition
1: functional group
2: double bond
3: triple bond
4: substituent |
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Term
| how to account for functional groups when naming molecules |
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Definition
placing the number in front of the suffix or in front of the parent chain
example:
hexan-2-ol or 2-hexanol |
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Term
| how to account for substituents when naming molecules |
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Definition
putting the number of the substituent immediately in front of the substituent
example:
2-chlorohexane |
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Term
| how to account for multiple substituents when naming molecules |
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Definition
| number each one alphabetize by substituent (not di, tri, tetra, etc.) |
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Term
| how to account for stereoisomerism when naming molecules |
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Definition
put it at the beginning of the name and number accordingly
example:
2-cis-4-trans or (2R,4S) |
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Term
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Definition
| the various positions available to a molecule |
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