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Orgo 1 > Ch 1 - Chem Review > Flashcards

Ch 1 - Chem Review Flashcards

1
Q

Organic compounds contain

A

carbon atoms

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2
Q

Constitutional isomers

A

share the same molecular formula but have different connectivity of atoms and different physical properties.

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3
Q

Each element will generally form a predictable number of bonds.

A

Carbon is generally tetravalent, nitrogen trivalent, oxygen divalent, and hydrogen and the halogens monovalent.

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4
Q

covalent bond

A

results when two atoms share a pair of electrons.

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5
Q

Covalent bonds are illustrated using Lewis structures,

A

in which electrons are represented by dots.

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6
Q

Second-row elements generally obey the octet rule,

A

bonding to achieve noble gas electron configuration.

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7
Q

lone pair.

A

A pair of unshared electrons

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8
Q

formal charge

A

occurs when atoms do not exhibit the appropriate number of valence electrons; formal charges must be drawn in Lewis structures.

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9
Q

Bonds are classified as

A

(1) covalent, (2) polar covalent, or (3) ionic.

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10
Q

Polar covalent bonds exhibit induction, causing the formation of partial positive charges and partial negative charges

A

Electrostatic potential maps present a visual illustration of partial charges.

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11
Q

Quantum mechanics

A

describes electrons in terms of their wavelike properties.

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12
Q

wave equation

A

describes the total energy of an electron when in the vicinity of a proton. Solutions to wave equations are called wavefunctions(W) , where W^2 represents the probability of finding an electron in a particular location.

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13
Q

Atomic orbitals

A

are represented visually by generating three-dimensional plots of W^2; nodes indicate that the value of W is zero.

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14
Q

electron density

A

An occupied orbital can be thought of as a cloud

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15
Q

Electrons fill orbitals following three principles:

A

(1) the Aufbau principle, (2) the Pauli exclusion principle, and (3) Hund’s rule. Orbitals with the same energy level are called degenerate orbitals.

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16
Q

Valence bond theory

A

treats every bond as the sharing of electron density between two atoms as a result of the constructive interference of their atomic orbitals. Sigma (σ) bonds are formed when the electron density is located primarily on the bond axis.

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17
Q

Molecular orbital theory

A

uses a mathematical method called the linear combination of atomic orbitals (LCAO) to form molecular orbitals. Each molecular orbital is associated with the entire molecule, rather than just two atoms.

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18
Q

The bonding MO of molecular hydrogen results from

A

constructive interference between its two atomic orbitals

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19
Q

The antibonding MO results from

A

destructive interference.

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20
Q

atomic orbital

A

is a region of space associated with an individual atom, while a molecular orbital is associated with an entire molecule.

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21
Q

Two molecular orbitals are the most important to consider:

A

(1) the highest occupied molecular orbital, or HOMO, and (2) the lowest unoccupied molecular orbital, or LUMO.

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22
Q

Methane’s tetrahedral geometry can be explained using

A

four degenerate sp^3-hybridized orbitals to achieve its four single bonds.

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23
Q

Ethylene’s planar geometry can be explained using

A

three degenerate sp2-hybridized orbitals. The remaining p orbitals overlap to form a separate bonding interaction, called a pi bond. The carbon atoms of ethylene are connected via a sigma bond, resulting from the overlap of sp2-hybridized atomic orbitals, and via a pie bond, resulting from the overlap of p orbitals, both of which comprise the double bond of ethylene.

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24
Q

Acetylene’s linear geometry is achieved via

A

sp-hybridized carbon atoms in which a triple bond is created from the bonding interactions of one sigma bond, resulting from overlapping sp orbitals, and two pie bonds, resulting from overlapping p orbitals.

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25
Q

Triple bonds are stronger and shorter than

A

double bonds, which are stronger and shorter than single bonds.

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26
Q

The geometry of small compounds can be predicted using valence shell electron pair repulsion (VSEPR) theory, which focuses on

A

sigma bonds and lone pairs exhibited by each atom. The total, called the steric number, indicates the number of electron pairs that repel each other.

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27
Q

A tetrahedral arrangement of orbitals indicates

A

sp^3 hybridization (steric number 4). A compound’s geometry depends on the number of lone pairs and can be tetrahedral, trigonal pyramidal, or bent.

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28
Q

A trigonal planar arrangement of orbitals indicates

A

sp^2 hybridization (steric number 3); however, the geometry may be bent, depending on the number of lone pairs.

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29
Q

Linear geometry indicates

A

sp hybridization (steric number 2)

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30
Q

Dipole moments (U)

A

occur when the center of negative charge and the center of positive charge are separated from one another by a certain distance; the dipole moment is used as an indicator of polarity (measured in debyes).

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31
Q

The percent ionic character of a bond is determined by

A

measuring its dipole moment. The vector sum of individual dipole moments in a compound determines the molecular dipole moment.

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32
Q

The physical properties of compounds are determined by

A

intermolecular forces, the attractive forces between molecules.

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33
Q

Dipole-dipole interactions occur between two molecules that possess

A

permanent dipole moments. Hydrogen bonding, a special type of dipole-dipole interaction, occurs when the lone pairs of an electronegative atom interact with an electron-poor hydrogen atom. Compounds that exhibit hydrogen bonding have higher boiling points than similar compounds that lack hydrogen bonding.

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34
Q

London dispersion forces result from the interaction between

A

transient dipole moments and are stronger for larger alkanes due to their larger surface area and ability to accommodate more interactions.

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35
Q

Polar compounds are soluble in

A

polar solvents

36
Q

nonpolar compounds are soluble in

A

nonpolar solvents.

37
Q

Soaps are compounds that contain both

A

hydrophilic and hydrophobic regions. The hydrophobic tails surround nonpolar compounds, forming a water-soluble micelle.

38
Q

Organic Chemistry

A

the study of carbon based molecules

39
Q

constitutional isomers

A

same molecular formula but differ in the way the atoms are connected

  • different names and physical properties
40
Q

each element will generally form a predictable number of bonds

A
  • tetravalent(4 bonds)
  • trivalent(3 bonds)
  • divalent(2 bonds)
  • monovalent(1 bond)
41
Q

covalent bond

A

two atoms sharing a pair of electrons

42
Q

Lewis Structure

A

a drawing style in which electrons take center stage

43
Q

Lewis structures are based on

A

the valence electrons pairing up to be shared between atoms

44
Q

Identifying Formal Charge

A

2 steps

	- determine the appropriate number of valence electrons for an atom
	- determine whether the atom exhibits the appropriate number of electrons
45
Q

formal charge =

A

valence – nonbonded-1/2(bonded)

- N is 5A but has 4 electrons = +
- O is 6A but has 7 electrons = -
46
Q

three bond categories

A
  • covalent(sharing)
    - polar covalent(uneven sharing)
    - ionic(electron transfer)
47
Q

the bond type is based on

A

the electronegativity(measure of an atoms ability to attract electrons) difference of two atoms

48
Q

General guideline for electronegativity(not definitive)

A
  • 0.0-0.5 is covalent(C-C)
    - 0.5-1.7 is polar covalent bond(C-O)
    - 1.7+ is ionic(NaOH)
49
Q

induction

A

the withdrawal of electron density that occurs when a bond is shared by to atoms of differing electronegativity

50
Q

electrons are particles with

A

wavelike properties

51
Q

quantum mechanics

A

a mathematical description of an electron that incorporates its wavelike properties

52
Q

wave equation

A

describes the total energy of a hydrogen atom(one proton plus one electron
- takes into account the wavelike behavior of an electron that is in the electric field of a proton

53
Q

wave functions(W)

A

a series of solutions to the wave equation

		- each wavefunction corresponds to an allowed energy level for the electron
		- suggest electrons only exists at discrete energy levels(W1,W2,W3 etc)
		- energy of an electron is quantized
54
Q

each wavefunction is a function of spatial location

A
  • provides information that allows numerical value to be assigned
    - W^2 indicates the probability of finding the electron in that location
    - these are SPDF orbitals
55
Q

orbital

A

a region of space that can be occupied by an electron

- remember: an electron is part particle and part wavelike

56
Q

electron clouds only come in a

A

small number of shapes and sizes(defined by the orbitals)

57
Q

an electron cloud is a

A

single entity

58
Q

electron density

A

a term associated with the probability of finding an electron in a particular region of space

59
Q

the “shape” of an orbital refers to a region of space that contains 90-95% of the electron density

A
  • 100% density would literally be the entire universe
60
Q

atomic orbital(AO)

A

a 3-D plot of W^2 of a wavefunction

	- region of space that can accommodate electron density
	- SPDF
61
Q

for a wave function(W):

A
  • Red means above average(+)
    - Blue means below average(-)
    - node – in atomic and molecular orbitals a location where W is zero
    - does NOT denote positive or negative charge
    - simply denotes the phase of a wave
    - a node has an electron density of zero
62
Q

node

A

in atomic and molecular orbitals a location where W is zero

63
Q

Orbitals are filled by electrons guided by 3 principles

A
  • Aufbau principle – the lowest energy orbital is filled first
    - Pauli exclusion principle – each orbital can accommodate a maximum of two electrons that have opposite spin(up and down spin)
    - Hunds Rule – when dealing with degenerate orbitals, such as p orbitals, one electron is placed in each degenerate orbital first before electrons are paired up
64
Q

Aufbau principle

A

the lowest energy orbital is filled first

65
Q

Pauli exclusion principle

A

each orbital can accommodate a maximum of two electrons that have opposite spin(up and down spin)

66
Q

Hunds Rule

A

when dealing with degenerate orbitals, such as p orbitals, one electron is placed in each degenerate orbital first before electrons are paired up

67
Q

a covalent bond is formed from the overlap of

A

atomic orbitals

68
Q

constructive interference

A

two waves create a wave with larger amplitude

69
Q

destructive interference

A

two waves interferences cancels each other out producing a node

70
Q

valence bond theory

A

a bond is simply the sharing of electron density between two atoms as a result of the constructive interference of their atomic orbitals

71
Q

sigma bond

A

circular symmetry with respect to the bond axis

72
Q

all single bonds are ____bonds(head on the axis)

A

sigma

73
Q

molecular orbital(MO) theory

A

describes a bond in terms of the constructive interference between two overlapping atomic orbitals
- linear combination of atomic orbitals(LCAO)

74
Q

molecular orbitals

A

mathematically derived orbitals, hybrids

75
Q

atomic orbits are a region of space associated with

A

the atom

76
Q

molecular orbitals are an orbital associated with

A

the entire molecule

77
Q

bonding MO

A

the lower energy MO filled first via constructive interference

78
Q

antibonding MO

A

higher energy MO filled after bonding MO via destructive interference

79
Q

important MOs

A
  • highest occupied molecular orbital(HOMO)

- lowest unoccupied molecular orbital(LUMO)

80
Q

dipole moment(U)

A

an indicator of polarity

	- U = (partialcharge)(d)
	- partial + and – are usually in order of 10^-10esu(electrostatic units)
	- U will generally have a magnitude of 10^-18 esu
	- 1 debye(D) = 10^-18 (esu)(cm)
	- %ionic is (actual D/theoretical 100% D)(100%)
81
Q

molecular dipole moment

A

the vector sums of multiple dipole moments in a molecule to get the molecule dipole moment

82
Q

stronger bonds =

A

higher boiling point

83
Q

longer straight chain has more surface area =

A

higher boiling point

84
Q

branching results in less surface area and

A

a lower boiling point

85
Q

hydrophilic

A

water loving

86
Q

hydrophobic

A

water hating

87
Q

micelle

A

polar heads and nonpolar tails ball u and become water soluble(polar heads out)

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