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Organic Chemistry > Semester 1 Review > Flashcards

Semester 1 Review Flashcards

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1
Q

What are isomers

A

Different molecules having the same molecular formula

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2
Q

What kind of bonds does a molecule have?

A

Covalent

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3
Q

What kind of bonds does a compound have?

A

Either ionic or covalent

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4
Q

What is a resonance structure?

A

2 Lewis structures having the same placement of atoms but a different arrangement of electrons.

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5
Q

What is the difference between an isomer and a resonance structure?

A

isomers differ in arrangement of atoms and electrons, resonance structures differ ONLY in arrangement electrons

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6
Q

rules for drawing resonance structures

A
  1. two resonance structure differ in position of multiple bonds and nonbonded electrons
  2. 2 resonance structures must have same number of unpaired electrons
  3. resonance structures must be valid Lewis structures
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7
Q

situations where two different resonance structures can be drawn:

A

when a lone pair is located on an atom directly bonded to a multiple bond
when an atom bearing a (+) charge is bonded to either a multiple bond or an atom with a lone pair

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8
Q

size of atom ____ across a row of the periodic table

A

decreases

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9
Q

size of atom ______ down a column of the periodic table

A

increases

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10
Q

what is the bond angle for a linear molecule?

A

180°

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11
Q

What is the bond angle for trigonal planar molecular geometry? (3 groups around an atom)

A

120°

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12
Q

What is the bond angle for tetrahedral molecular geometry? (4 groups around an atom)

A

109.5°

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13
Q

what is a heteroatom?

A

any atom that is not C or H

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14
Q

what is ground state

A

lowest energy arrangement of electrons

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15
Q

hybridization

A

the combination of 2 or more atomic orbitals to form the same number of hybrid orbitals, each having the same shape and energy (i.e. sp^3)

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16
Q

As the number of electrons between two nuclei increases, bonds become _____ and ____

A

shorter and stronger

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17
Q

single bonds are ______ than double bonds, which are ____ than triple bonds

A

longer and weaker, longer and weaker

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18
Q

Csp-H bonds are ____ and ____ than Csp2-H bonds, which are ___ and ___ than Csp3-H bonds

A

shorter and stronger

shorter and stronger

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19
Q

as percent s-character increases, what happens to the bond length and strength?

A

the bond becomes shorter and stronger with increasing s-character
s orbitals keep electrons closer to the nucleus than p orbitals

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20
Q

what is electronegativity?

A

a measure of an atom’s attraction for electrons in a bond

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21
Q

what happens to electronegativity as you travel across a row in the periodic table?

A

it increases from left to right as the nuclear charge increases (more valence electrons

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22
Q

what happens to electronegativity as you travel down a column in the periodic table?

A

electronegativity decreases as you go down a column - atomic radius increases, pushing valence electrons farther from nucleus

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23
Q

in a polar bond, which atom pulls electrons closer?

A

The more electronegative atom - the one with the higher electronegative value.

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24
Q

what is a dipole?

A

a separation of charge in a bond - a polar bond

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25
when is a bond considered polar?
when the electronegativity difference between the two atoms is greater than or equal to .5 (usually)
26
What is a Brønsted-Lowry acid?
a proton donor
27
what is a Brønsted-Lowry base?
a proton acceptor
28
a Brønsted-Lowry acid must contain what kind of atom?
hydrogen
29
what must a Brønsted-Lowry base contain?
a lone pair of electrons or a pi bond
30
what is acid strength?
the tendency of an acid to donate a proton | the more readily a compound donates a proton, the stronger the acid
31
How does Ka relate to acid strength?
the stronger the acid, the higher the Ka value
32
how does pKa relate to acid strength?
the smaller the pKa, the stronger the acid
33
a strong acid has what kind of conjugate base?
a weak conjugate base
34
equilibrium favors the formation of the stronger acid and base or the weaker acid and base?
the weaker acid and base
35
how can you tell if a particular base is strong enough to deprotonate a given acid?
compare the PKa values of the acid and the base's conjugate acid. The base can deprotonate a given acid if the base's conjugate acid's PKa value is higher than the given acid's PKa value.
36
How can you tell which acid is more acidic?
the more stable the conjugate base, the more acidic the acid
37
What four factors affect the acidity of H-A?
1) elemental effects 2) inductive effects 3) resonance effects 4) hybridization effects
38
what is the most important determining factor determining the acidity of H-A?
the location of A in the periodic table
39
across which directions in the periodic table does the acidity of H-A increase?
acidity of H-A increases both left to right across a row and down a column of the periodic table
40
what is an inductive effect?
pull of electron density through sigma bonds caused by electronegativity differences of atoms
41
how does the presence of electron-withdrawing groups in A affect the acidity of H-A?
acidity of H-A increases with the presence of electron-withdrawing groups in A, because of the electron-withdrawing inductive effect
42
an electronegative atom does what to a negative charge?
stabilizes it
43
how does resonance affect acidity?
acidity of H-A increases when the conjugate baseA:- is resonance stabilized. (2 or more structures can be drawn that are the same except for pi bonds and lone pair positions)
44
how does percent s character (hybridization) affect the acidity of H-A?
the acidity of H-A increases as the percent s-character of the A:- increases.
45
what is a Lewis acid?
an electron pair acceptor | any species that is electron deficient and capable of accepting an electron pair
46
what is a Lewis base?
an electron pair donor
47
what is an electrophile?
a Lewis acid - something that wants electrons
48
what is a nucleophile?
a Lewis base that reacts with an electrophile other than a proton has a lone pair or a pi bond
49
why do heteroatoms confer reactivity on a particular molecule?
they have lone pairs and create electron-deficient sites on C
50
why do Pi bonds confer reactivity on a particular molecule?
Pi bonds are easily broken in chemical reactions. a Pi bond makes a molecule a base and a nucleophile
51
what are van der Waals forces?
weak interactions caused by the momentary changes in electron density in a molecule. they can induce temporary dipoles in another non-polar molecule arranging themselves with negative and positive temporary forces close to each other. All compounds exhibit van der Waals forces
52
how does surface area of a molecule determine the strength of van der Waals interactions?
The larger the surface area, the larger the attractive force between two molecules, and the stronger the intermolecular forces.
53
What is polarizability
measure of how the electron cloud around an atom responds to changes in its electronic environment
54
how does size affect polarizability?
the larger an atom, the more loosely held the valence electrons are, the more polarizable the atom is.
55
what are dipole-dipole interactions?
the attractive forces between the permanent dipoles of two polar molecules
56
what is hydrogen bonding?
occurs when an H atom bonded to O, N, or F is electrostatically attracted to a lone pair of electrons on an O, N, or F atom in another molecule
57
list the 4 types of intermolecular forces from weakest to strongest
van der Waal dipole-dipole hydrogen bonding ionic
58
how do intermolecular forces affect boiling point?
the stronger the intermolecular forces, the higher the boiling point
59
for two compounds with similar functional groups, how do surface area and polarizability affect the boiling point?
the larger the surface area, the higher the boiling point | the more polarizable the atoms, the higher the boiling point
60
how do intermolecular forces affect melting point?
the stronger the intermolecular forces, the higher the melting point
61
how does symmetry affect melting point?
given the same functional group, the more symmetrical the compound, the higher the melting point
62
what is a saturated hydrocarbon?
CnH2n+2 they have the maximum number of H atoms per C
63
what is the IUPAC name for isobutane?
2-methylpropane
64
how is a sec-butyl group formed?
removal of a 2°H from butane
65
how is an isobutyl group formed?
removal of a 1°H from isobutane
66
how is a tert-butyl group formed?
removal of a 3°H from isobutane
67
what makes a good leaving group?
a weak base - better able to hold a negative charge
68
what are the periodic trends in leaving group ability?
left to right across a row, leaving group ability increases | down a column, leaving group ability increases
69
how can you use pKa value to determine if a group's leaving ability?
the conjugate acid must be strong. pKa of conjugate acid must be low
70
what is the difference between a base and a nucleophile?
bases attack protons, nucleophiles attack carbons

Organic Chemistry (6 decks)

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