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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
Q

when is a bond considered polar?

A

when the electronegativity difference between the two atoms is greater than or equal to .5 (usually)

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26
Q

What is a Brønsted-Lowry acid?

A

a proton donor

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27
Q

what is a Brønsted-Lowry base?

A

a proton acceptor

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28
Q

a Brønsted-Lowry acid must contain what kind of atom?

A

hydrogen

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29
Q

what must a Brønsted-Lowry base contain?

A

a lone pair of electrons or a pi bond

30
Q

what is acid strength?

A

the tendency of an acid to donate a proton

the more readily a compound donates a proton, the stronger the acid

31
Q

How does Ka relate to acid strength?

A

the stronger the acid, the higher the Ka value

32
Q

how does pKa relate to acid strength?

A

the smaller the pKa, the stronger the acid

33
Q

a strong acid has what kind of conjugate base?

A

a weak conjugate base

34
Q

equilibrium favors the formation of the stronger acid and base or the weaker acid and base?

A

the weaker acid and base

35
Q

how can you tell if a particular base is strong enough to deprotonate a given acid?

A

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
Q

How can you tell which acid is more acidic?

A

the more stable the conjugate base, the more acidic the acid

37
Q

What four factors affect the acidity of H-A?

A

1) elemental effects
2) inductive effects
3) resonance effects
4) hybridization effects

38
Q

what is the most important determining factor determining the acidity of H-A?

A

the location of A in the periodic table

39
Q

across which directions in the periodic table does the acidity of H-A increase?

A

acidity of H-A increases both left to right across a row and down a column of the periodic table

40
Q

what is an inductive effect?

A

pull of electron density through sigma bonds caused by electronegativity differences of atoms

41
Q

how does the presence of electron-withdrawing groups in A affect the acidity of H-A?

A

acidity of H-A increases with the presence of electron-withdrawing groups in A, because of the electron-withdrawing inductive effect

42
Q

an electronegative atom does what to a negative charge?

A

stabilizes it

43
Q

how does resonance affect acidity?

A

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
Q

how does percent s character (hybridization) affect the acidity of H-A?

A

the acidity of H-A increases as the percent s-character of the A:- increases.

45
Q

what is a Lewis acid?

A

an electron pair acceptor

any species that is electron deficient and capable of accepting an electron pair

46
Q

what is a Lewis base?

A

an electron pair donor

47
Q

what is an electrophile?

A

a Lewis acid - something that wants electrons

48
Q

what is a nucleophile?

A

a Lewis base that reacts with an electrophile other than a proton
has a lone pair or a pi bond

49
Q

why do heteroatoms confer reactivity on a particular molecule?

A

they have lone pairs and create electron-deficient sites on C

50
Q

why do Pi bonds confer reactivity on a particular molecule?

A

Pi bonds are easily broken in chemical reactions. a Pi bond makes a molecule a base and a nucleophile

51
Q

what are van der Waals forces?

A

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
Q

how does surface area of a molecule determine the strength of van der Waals interactions?

A

The larger the surface area, the larger the attractive force between two molecules, and the stronger the intermolecular forces.

53
Q

What is polarizability

A

measure of how the electron cloud around an atom responds to changes in its electronic environment

54
Q

how does size affect polarizability?

A

the larger an atom, the more loosely held the valence electrons are, the more polarizable the atom is.

55
Q

what are dipole-dipole interactions?

A

the attractive forces between the permanent dipoles of two polar molecules

56
Q

what is hydrogen bonding?

A

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
Q

list the 4 types of intermolecular forces from weakest to strongest

A

van der Waal
dipole-dipole
hydrogen bonding
ionic

58
Q

how do intermolecular forces affect boiling point?

A

the stronger the intermolecular forces, the higher the boiling point

59
Q

for two compounds with similar functional groups, how do surface area and polarizability affect the boiling point?

A

the larger the surface area, the higher the boiling point

the more polarizable the atoms, the higher the boiling point

60
Q

how do intermolecular forces affect melting point?

A

the stronger the intermolecular forces, the higher the melting point

61
Q

how does symmetry affect melting point?

A

given the same functional group, the more symmetrical the compound, the higher the melting point

62
Q

what is a saturated hydrocarbon?

A

CnH2n+2 they have the maximum number of H atoms per C

63
Q

what is the IUPAC name for isobutane?

A

2-methylpropane

64
Q

how is a sec-butyl group formed?

A

removal of a 2°H from butane

65
Q

how is an isobutyl group formed?

A

removal of a 1°H from isobutane

66
Q

how is a tert-butyl group formed?

A

removal of a 3°H from isobutane

67
Q

what makes a good leaving group?

A

a weak base - better able to hold a negative charge

68
Q

what are the periodic trends in leaving group ability?

A

left to right across a row, leaving group ability increases

down a column, leaving group ability increases

69
Q

how can you use pKa value to determine if a group’s leaving ability?

A

the conjugate acid must be strong. pKa of conjugate acid must be low

70
Q

what is the difference between a base and a nucleophile?

A

bases attack protons, nucleophiles attack carbons

Organic Chemistry (6 decks)

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