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Organic Chem > Unit 1 > Flashcards

Unit 1 Flashcards

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1
Q

what would the electron geometry be of an atom with a steric number of 3

A

trigonal planar

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2
Q

why is H an exception to the octet rule

A

it can’t hold 8 electrons

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3
Q

what is the normal valence for B? when is it positive? negative?

A
  • 3 bonding pairs, 0 lone pairs (octet rule violation)
  • it doesn’t occur
  • 4 bonding pairs and 0 lone pairs * same as aluminum
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4
Q

when woould an atom with a tetrahedral electron geometry (s# = 4) have a bent molecular geometry

A

when there are two sigma bonds and two lone pairs

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5
Q

in the electron geometry of a molecule is trigonal planar (s# = 3), what bond configuration would result in a bent molecular geometry

A

2 sigma bonds, one non bonding pair, one pi bond

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6
Q

steps for drawing lewis structures (5)

A
  1. determine the number of valence electrons in every atom of the molecule
  2. if the molecule is (-), add one electron, if its (+), subtract one
  3. connect all atoms of the molecule with one bonding pair
  4. distribute the remaining electrons as lone pairs, starting with the outermost atoms first
  5. if there are any atoms that don’t have a full octet, change one lone pair of a full atom that will form the lowest charge to a bonding pair
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7
Q

if an atom has a tetrahedral electron arrangement and bent molecular arrangement, what will the bond angles be

A

104.5

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8
Q

when would you find a negative halogen

A

inorganic free ions (fluoride, chloride, bromide)

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9
Q

normal valence

A

the number of bonds an atom has when it is neutral

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10
Q
  • what type of functional group is this?
  • what are the restrictions on R groups
A
  • epoxides
  • none, R can be C or O
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11
Q

constructive interference

A

when the interaction of two waves meeting produces a larger wave

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12
Q

what is the normal valence for S (12e-) when is it positive? negative?

A
  • 6 bonding pairs and 0 lone pairs
  • doesn’t occur
  • 5 bonding pairs and 1 lone pair
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13
Q

sigma bonds

A

single bonds formed by the direct overlap of orbitals

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14
Q

why are S and P exceptions to the octet rule

A

Sulfur and phosphorus both can have 10 e- and still be neutral

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15
Q

when woould an atom with a tetrahedral electron geometry (s# = 4) have a tetrahedral molecular geometry

A

when there are 4 sigma bonds

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16
Q

pauli principle

A

each orbital can only hold two electrons

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17
Q

how many valence electrons do oxygen and sulfur have

A

6

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18
Q

what are two possible orientations of alkynes

A

terminal

internal

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19
Q

what do parentheses do in condensed structures

A
  • they can be used with subscripts to indicate a repeating molecule (CH3CH2CH2CH3 becomes CH3(CH2)2CH3)
  • they can used to indicate branching atoms
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20
Q

what is the difference between primary, secondary, teritary alkyl halides

A

primary: 2R’s = H, 1R = C
secondary: 2R = C
tertiary: 3R = C

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21
Q

when forming positive ions in a charged molecule, which elements should be made into ions first

A

Sulfur, nitrogen, oxygen, carbon

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22
Q

T/F the charge on a molecule must always be determined

A

False, the charge of molecule is always neutral unless otherwise stated

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23
Q

what does the psi value indicate

A

the phase of the electron in the cloud, + on one side of the atom, - on the other

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24
Q

what is the difference between primary, secondary, and tertiary alcohols

A

primary: 2R’s = H, 1R = C
secondary: 2R’s = C
tertiary: 3R’s = C

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25
Q

condensed structure (example)

A

no bonds are drawn, just clusters of C and H (CH3CH2CH2CH2CH3)

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26
Q

what does a 0 psi value indicate

A

a node, a place where the likelihood of finding an electron is zero

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27
Q
  • what type of functional group is this
  • what are the restrictions on the R groups
A
  • alcohol
  • R can be C or H, but it can’t be C=O
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28
Q
  • what functional group is this?
  • what are the restrictions on the R groups
A
  • amide
  • can be C or H
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29
Q
  • what type of functional group is this?
  • what are the restrictions on the R groups
A
  • ketone
  • the R groups have to be C
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30
Q

what elements are exceptions to the octet rule (6)

A

H, B, Al, P, S, C

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31
Q

how many valence electrons does carbon have

A

4

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32
Q

pi bonds

A

double or triple bonds formed by the interaction of parallel p orbitals

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33
Q

when is carbon negatively charged

A

when it has 3 bonding pairs and 1 lone pair

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34
Q

what creates nodes

A

destructive interference

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35
Q

what is the normal valence for S (10e-) when is it positive? negative?

A
  • 4 bonding pairs and 1 lone pair
  • 5 bonding pairs
  • 3 bonding pairs and 2 lone pairs
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36
Q

how do atoms form covalent bonds

A

by overlapping orbital levels in the same phase

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37
Q

steric number

A

the number of groups in an atom that repel each other

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38
Q

what are cyclic esters called

A

lactones

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39
Q

what is a special circumstance where a trigonal planar electron geometry can produce a trigonal planar molecular geometry with only 3 bonds

A

in a carbocation, a neutral boron, or a neutral aluminum

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40
Q

what is the difference between primary, secondary, and tertiary amines

A

primary: 2R’s = H, 1R = C
secondary: 2R’s = C
tertiary: 3R = C

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41
Q

hund’s rule

A

electrons in an orbital are unpaired unless necessary

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42
Q

what would produce a linear electron geometry? what is the molecular geometry?

A

a steric number of 2 with 2 sigma bonds and two pi bonds

linear

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43
Q

what is the normal valence of a halogen? when are they positive? negative?

A
  • 1 bonding pair and 3 lone pairs
  • 2 bonding pairs and 2 lone pairs
  • 0 bonding pairs and 4 lone pairs
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44
Q

T/F Terminal alkynes are basic

A

false, they are extremely acidic compared to other carbons

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45
Q

in the electron geometry of a molecule is trigonal planar (s# = 3), what bond configuration would result in a trigonal planar molecular geometry

A

three sigma bonds and one pi bond

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46
Q

hybridized orbitals

A

orbitals created during bond formation through the mixing of orbital levels to form new orbitals of lower energy

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47
Q

atomic orbital

A

the region of space that can be occupied by an electron

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48
Q

what are the three possibe electron geometries in organic chem

A

tetrahedral, trigonal planar, and linear

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49
Q

how many valence electrons do halogens have (Cl, Br, F, I)

A

7

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50
Q
  • what type of functional group is this?
  • what are the restrictions on R groups
A
  • alkyne
  • none, can be C or H
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51
Q

when forming negative ions in a charged molecule, which elements should be made into ions first

A

sulfur, oxygen, nitrogen, carbon

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52
Q

what is the normal valence for H? when is it positive? negative?

A
  • 1 bonding pair
  • as a hydrogen ion
  • as a hydride with 1 electron pair
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53
Q

what is the difference between primary, secondary, and tertiary thiols

A

primary: 2R’s = H, 1R =C
secondary: 2R’s = C
tertiary: 3R = C

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54
Q

molecular formula (example)

A

lists atoms but doesn’t provide connectivity (CO2)

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55
Q

what is the normal valence of nitrogen? when is it positive? negative?

A
  • 3 bonding pair and 1 lone pair
  • 4 bonding pairs
  • 2 bonding pairs and two lone pairs *same as phosphorus
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56
Q

what is the effect of hybridized orbitals on overall energy

A

the hybridized orbital lowers energy

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57
Q

when a parentheses are used to indicate branching atoms, what is the format

A

the atoms in parentheses are branch off the carbon immediately before or after the parentheses

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58
Q

how many carbons, hydrogens, and oxygens are in this molecule

A

4 carbons, 8 hydrogens, 2 oxygens

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59
Q

what are cyclic amides called

A

lactams

60
Q

if an atom has a tetrahedral electron arrangement and trigonal planar molecular arrangement, what will the bond angles be

A

107.5

61
Q
  • what type of functional group is this?
  • is R a C or H?
  • is R’ a C or H?
A
  • an ester
  • it can be a C or H
  • it must be C, and it can’t be double bonded to an O
62
Q

T/F when hybridizing, the number of orbitals can increase or decrease

A

false, the number of orbitals is conserved

63
Q

what is the normal valence of carbon

A

when it has four bonding pairs

64
Q

in organic chemistry what are the possible steric number values

A

4, 3, and 2

65
Q

Aufbau principle

A

electrons are placed in the lowest energy levels first

66
Q

what is the effect of hybridized orbitals on electron density

A

hybridized orbitals increase electron density between the bonded atoms

67
Q

how to determine steric number

A

of sigma bonds + the number of lone pairs

68
Q

if an atom has a trigonal planar electron arrangement what will the bond angles be

A

120

69
Q

why do sp3 orbitals have high energy than other sp orbitals

A

sp3 bonds are all sigma bonds with direct overlap of orbitals, sp and sp2 have pi bonds which rely on indirect interaction

70
Q

what is the normal valence for P (10e-) when is it positive? negative?

A
  • 5 bonding pairs
  • doesn’t occur
  • 4 bonding pairs and 1 lone pair
71
Q
  • what type of functional group is this
  • what are the restrictions on the R groups
A
  • ether
  • R will be a C with three R’s (can be C or H, but not C=O)
72
Q
  • what type of functional group is this?
  • what is the X group?
  • what are the restrictions on the R group
A
  • alkyl halide
  • x is the halogen
  • R can be H or C but no C=O
73
Q

what is the normal valence for Al? when is it positive? negative?

A
  • 3 bonding pairs, 0 lone pairs (octet rule violation)
  • it doesn’t occur
  • 4 bonding pairs and 0 lone pairs * same as boron
74
Q

why are pi bonds not counted in steric number

A

because the pi bonds are considered to be overlapping an existing sigma bond

75
Q

why are Al and B exceptions to the octet rule

A

neutral boron and aluminum only has 3 bonding pairs and 0 lone pairs

76
Q
  • what functional group is this?
  • what are the restrictions on the R group
A
  • alkene
  • none, can be C or H
77
Q
  • what type of functional group is this?
  • what are the restrictions on the R groups
A
  • aldehyde
  • none, can be H or C
78
Q

destructive interference

A

when the phase of two waves is out of sync and creates a wave of lower amplitude

79
Q
  • what type of functional group is this?
  • what are the restrictions are the R group
A
  • amine
  • R can be H or C, but not C=O
80
Q

when is carbon positive

A

when it has 3 bonding pairs and lone pairs

81
Q
  • what type of functional group is these
  • what is the S
A
  • aromatic rings
  • a heteroatom with at least one nonbonding pair
82
Q

what is the normal valence of sulfur? when is it positive? when is it negative?

A
  • 2 bonding pairs and 2 lone pairs
  • 3 bonding pairs and one lone pair
  • 1 bonding pair and three lone pairs *same as oxygen
83
Q

how many bonds will a neutral carbon have? oxygen?

A

4, 2

84
Q

partially condensed structure (example)

A

CH bonds are not drawn (CH3 - CH2 - CH2 - CH2 - CH3)

85
Q

if an atom has a tetrahedral electron arrangement and tetrahedral molecular arrangement, what will the bond angles be

A

109.5

86
Q

how many valence electrons do nitrogen and phosphorus have

A

5

87
Q

when distributing charge, should the charge go to the larger or the smaller atom

A

the larger atom

88
Q

two types of covalent bonds

A
  • sigma bonds
  • pi bonds
89
Q

T/F all hydrogen bonds will be drawn in bond-line drawings

A

false hydrogen bonds are understood if a carbon has less than four bond

90
Q

what steric number will result in a tetrahedral electron arrangement

A

4

91
Q

when woould an atom with a tetrahedral electron geometry (s# = 4) have a trigonal planarmolecular geometry

A

when there are three sigma bonds and 1 lone pair

92
Q

what is the normal valence of phosphorus? when is it positive? negative

A
  • 3 bonding pair and 1 lone pair
  • 4 bonding pairs
  • 2 bonding pairs and two lone pairs *same as nitrogen
93
Q

heteroatoms

A

atoms other than carbon and hydrogen in an organic compound

94
Q

what is meant by the shape of the orbital

A

the region where an e- will be found 90% of the time

95
Q

T/F psi value is indicative of charge

A

false, it indicates the position of the electron relative to the atom

96
Q

what are the four possible molecular geometries in organic chem

A

tetrahedral, trigonal planar, bent, linear

97
Q

what is the difference in shape between a unhybridized p and a hybridized sp orbital

A

the unhybridized p has a symmetrical dumbbell shape, while the hybridized p has one side that is smaller and closer to the nucleus and one larger more extended side

98
Q
  • what function group is this?
  • what are the restrictions on the R groups
A
  • thiol
  • can be C or H, but not C=O
99
Q
  • what type of functional group is this?
  • what ran be the R group?
A
  • a carboxylic acid
  • it can be an C or H
100
Q

what are the three types of hybridized orbitals? which has the highest energy

A

sp, sp2, sp3

the sp3 orbitals have the highest energy

101
Q

T/F in an organic molecule, atoms will never have a charge greater than +/- 1

A

true

102
Q

what is the normal valence of oxygen? when is positive? negative?

A
  • 2 bonding pairs and 2 lone pairs
  • 3 bonding pairs and one lone pair
  • 1 bonding pair and three lone pairs *same as sulfur
103
Q

how to calculate formal charge

A

Fc = # of valence electrons - # of bonding pairs - # individual nonbonding electrons

104
Q

alkane

A

a simple organic compound made of only of C an H with sigma bonds

105
Q

what is the general formula for alkanes

A

CnH2n+2

106
Q

how are alkanes classified

A

the longest number of consequtive carbons

107
Q

what is the suffix for an alkane

A

ane

108
Q

substituents

A

carbon atoms that are not part of the long carbon alkane

109
Q

what suffix indicates a substituent alkane

A

-yl

110
Q

methane, -yl

A

a single carbon alkane or substituent

111
Q

ethane, -yl

A

a 2C alkane or substituent

112
Q

propane, -yl

A

a 3C alkane or substituent

113
Q

butane, -yl

A

a 4C alkane or substituent

114
Q

pentane, -yl

A

a 5C alkane or substituent

115
Q

hexane, -yl

A

a 6C alkane or substituent

116
Q

heptane, -yl

A

a 7C alkane or substituent

117
Q

octane, -yl

A

a 8C alkane or substituent

118
Q

nonane, -yl

A

a 9C alkane or substituent

119
Q

decane, -yl

A

a 10C alkane or substituent

120
Q

what is added to ring shaped alkane

A

cyclo

121
Q

T/F in the word cyclohexane, the H is used to alphabetize

A

false, the C is considered part of the word

122
Q

how is an acyclic alkane named

A
  • use the longest number of carbon chains
  • if there are multiple chains of the same length, use the one that gives the first different branch between the chains the lowest number
  • tie breaker: use the branch with the first substituent alphabetically
123
Q

when is a ring considered the parent of a molecule

A

when it has and equal or greater number of C as the longest chain

124
Q

what is the structure of 3-ethyl-2methylhexane

A

a 6C chain with a 2C branch at 3 and a 1C branch at 2

125
Q

when naming a molecule, in what order are the branches listed

A

alphabetically

126
Q

what is the naming scheme when a molecule has a branch with substituents

A

the branch is placed in parentheses with the longest chain last

127
Q

describe the structure of 3-(1-methylethyl)heptane

A

a 7C alkane with a 2C branch at 3, with a 1C substituent at 1

128
Q

what is the naming scheme for halogen substituents (example)

is it alphabetical?

A
  • the ine suffix is replaced with o (chloro, bromo, iodo, fluoro)
  • alphabetical order still applies
129
Q

what is the naming scheme when multiple identical substiuents come off the same branch

A

number prefixes are used

130
Q

what are the number prefixes for multiple consituents

A
  • di
  • tri
  • tetra
  • penta
  • hexa
  • hepta
  • octa
131
Q

describe the structure of 2,2,5-tribromohexane

A

a 6C alkane with two bromines on 2 and one bromine on 5

132
Q

T/F numbered prefixes for multiple branches are considered in alphabetical ordering

A

false

133
Q

what alkane branches can have more than one name

A
  • propyl
  • butyl
  • pentyl
134
Q

when is a propyl group considered isopropyl

A

when the branch is attached to the middle C

135
Q

what are the 3 possible names for a butyl group

A
  • sec-butyl
  • iso-butyl
  • tert-butyl
136
Q

sec-butyl

A

a 4C chain attached at C2

137
Q

iso-butyl

A

a linear three carbon chain with a 1C branch that makes a Y

138
Q

tert-butyl

A

a C with 3 methyl groups attached

139
Q
A
  1. tert-butyl
  2. isobutyl
  3. sec-butyl
140
Q

two possible names for a pentyl group

A

iso pentyl and neopentyl

141
Q

isopentyl

A

a 4C chain with a methyl group at C3 that makes a Y

142
Q

neopentyl

A

a 3C chain with two methyl groups on C2 (looks like tert-butyl)

143
Q

T/F prefixes iso/neo/sec/tert are not considered part of name and not used alphabetically

A

false

144
Q

what is the arrangement of Rs in any primary functional group

A

2 Rs are H and 1 is C

145
Q

what is the arrangement of R’s in any secondary functional group

A

2 R’s are C and 1 is H

146
Q

what is the arrangement of R’s in any teritary functional group

A

all 3 Rs are C

Organic Chem (8 decks)

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