1
Q
what would the electron geometry be of an atom with a steric number of 3
A
trigonal planar
2
Q
why is H an exception to the octet rule
A
it can’t hold 8 electrons
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
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
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
6
Q
steps for drawing lewis structures (5)
A
- determine the number of valence electrons in every atom of the molecule
- if the molecule is (-), add one electron, if its (+), subtract one
- connect all atoms of the molecule with one bonding pair
- distribute the remaining electrons as lone pairs, starting with the outermost atoms first
- 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
7
Q
if an atom has a tetrahedral electron arrangement and bent molecular arrangement, what will the bond angles be
A
104.5
8
Q
when would you find a negative halogen
A
inorganic free ions (fluoride, chloride, bromide)
9
Q
normal valence
A
the number of bonds an atom has when it is neutral
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
11
Q
constructive interference
A
when the interaction of two waves meeting produces a larger wave
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
13
Q
sigma bonds
A
single bonds formed by the direct overlap of orbitals
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
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
16
Q
pauli principle
A
each orbital can only hold two electrons
17
Q
how many valence electrons do oxygen and sulfur have
A
6
18
Q
what are two possible orientations of alkynes
A
terminal
internal
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
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
21
Q
when forming positive ions in a charged molecule, which elements should be made into ions first
A
Sulfur, nitrogen, oxygen, carbon
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
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
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
25
condensed structure (example)
no bonds are drawn, just clusters of C and H (CH3CH2CH2CH2CH3)
26
what does a 0 psi value indicate
a node, a place where the likelihood of finding an electron is zero
27
* what type of functional group is this
* what are the restrictions on the R groups
* alcohol
* R can be C or H, but it can't be C=O
28
* what functional group is this?
* what are the restrictions on the R groups
* amide
* can be C or H
29
* what type of functional group is this?
* what are the restrictions on the R groups
* ketone
* the R groups have to be C
30
what elements are exceptions to the octet rule (6)
H, B, Al, P, S, C
31
how many valence electrons does carbon have
4
32
pi bonds
double or triple bonds formed by the interaction of parallel p orbitals
33
when is carbon negatively charged
when it has 3 bonding pairs and 1 lone pair
34
what creates nodes
destructive interference
35
what is the normal valence for S (10e-) when is it positive? negative?
* 4 bonding pairs and 1 lone pair
* 5 bonding pairs
* 3 bonding pairs and 2 lone pairs
36
how do atoms form covalent bonds
by overlapping orbital levels in the same phase
37
steric number
the number of groups in an atom that repel each other
38
what are cyclic esters called
lactones
39
what is a special circumstance where a trigonal planar electron geometry can produce a trigonal planar molecular geometry with only 3 bonds
in a carbocation, a neutral boron, or a neutral aluminum
40
what is the difference between primary, secondary, and tertiary amines
primary: 2R's = H, 1R = C
secondary: 2R's = C
tertiary: 3R = C
41
hund's rule
electrons in an orbital are unpaired unless necessary
42
what would produce a linear electron geometry? what is the molecular geometry?
a steric number of 2 with 2 sigma bonds and two pi bonds
linear
43
what is the normal valence of a halogen? when are they positive? negative?
* 1 bonding pair and 3 lone pairs
* 2 bonding pairs and 2 lone pairs
* 0 bonding pairs and 4 lone pairs
44
T/F Terminal alkynes are basic
false, they are extremely acidic compared to other carbons
45
in the electron geometry of a molecule is trigonal planar (s# = 3), what bond configuration would result in a trigonal planar molecular geometry
three sigma bonds and one pi bond
46
hybridized orbitals
orbitals created during bond formation through the mixing of orbital levels to form new orbitals of lower energy
47
atomic orbital
the region of space that can be occupied by an electron
48
what are the three possibe electron geometries in organic chem
tetrahedral, trigonal planar, and linear
49
how many valence electrons do halogens have (Cl, Br, F, I)
7
50
* what type of functional group is this?
* what are the restrictions on R groups
* alkyne
* none, can be C or H
51
when forming negative ions in a charged molecule, which elements should be made into ions first
sulfur, oxygen, nitrogen, carbon
52
what is the normal valence for H? when is it positive? negative?
* 1 bonding pair
* as a hydrogen ion
* as a hydride with 1 electron pair
53
what is the difference between primary, secondary, and tertiary thiols
primary: 2R's = H, 1R =C
secondary: 2R's = C
tertiary: 3R = C
54
molecular formula (example)
lists atoms but doesn't provide connectivity (CO2)
55
what is the normal valence of nitrogen? when is it positive? negative?
* 3 bonding pair and 1 lone pair
* 4 bonding pairs
* 2 bonding pairs and two lone pairs \*same as phosphorus
56
what is the effect of hybridized orbitals on overall energy
the hybridized orbital lowers energy
57
when a parentheses are used to indicate branching atoms, what is the format
the atoms in parentheses are branch off the carbon immediately before or after the parentheses
58
how many carbons, hydrogens, and oxygens are in this molecule
4 carbons, 8 hydrogens, 2 oxygens
59
what are cyclic amides called
lactams
60
if an atom has a tetrahedral electron arrangement and trigonal planar molecular arrangement, what will the bond angles be
107.5
61
* what type of functional group is this?
* is R a C or H?
* is R' a C or H?
* an ester
* it can be a C or H
* it must be C, and it can't be double bonded to an O
62
T/F when hybridizing, the number of orbitals can increase or decrease
false, the number of orbitals is conserved
63
what is the normal valence of carbon
when it has four bonding pairs
64
in organic chemistry what are the possible steric number values
4, 3, and 2
65
Aufbau principle
electrons are placed in the lowest energy levels first
66
what is the effect of hybridized orbitals on electron density
hybridized orbitals increase electron density between the bonded atoms
67
how to determine steric number
of sigma bonds + the number of lone pairs
68
if an atom has a trigonal planar electron arrangement what will the bond angles be
120
69
why do sp3 orbitals have high energy than other sp orbitals
sp3 bonds are all sigma bonds with direct overlap of orbitals, sp and sp2 have pi bonds which rely on indirect interaction
70
what is the normal valence for P (10e-) when is it positive? negative?
* 5 bonding pairs
* doesn't occur
* 4 bonding pairs and 1 lone pair
71
* what type of functional group is this
* what are the restrictions on the R groups
* ether
* R will be a C with three R's (can be C or H, but not C=O)
72
* what type of functional group is this?
* what is the X group?
* what are the restrictions on the R group
* alkyl halide
* x is the halogen
* R can be H or C but no C=O
73
what is the normal valence for Al? when is it positive? negative?
* 3 bonding pairs, 0 lone pairs (octet rule violation)
* it doesn't occur
* 4 bonding pairs and 0 lone pairs \* same as boron
74
why are pi bonds not counted in steric number
because the pi bonds are considered to be overlapping an existing sigma bond
75
why are Al and B exceptions to the octet rule
neutral boron and aluminum only has 3 bonding pairs and 0 lone pairs
76
* what functional group is this?
* what are the restrictions on the R group
* alkene
* none, can be C or H
77
* what type of functional group is this?
* what are the restrictions on the R groups
* aldehyde
* none, can be H or C
78
destructive interference
when the phase of two waves is out of sync and creates a wave of lower amplitude
79
* what type of functional group is this?
* what are the restrictions are the R group
* amine
* R can be H or C, but not C=O
80
when is carbon positive
when it has 3 bonding pairs and lone pairs
81
* what type of functional group is these
* what is the S
* aromatic rings
* a heteroatom with at least one nonbonding pair
82
what is the normal valence of sulfur? when is it positive? when is it negative?
* 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
how many bonds will a neutral carbon have? oxygen?
4, 2
84
partially condensed structure (example)
CH bonds are not drawn (CH3 - CH2 - CH2 - CH2 - CH3)
85
if an atom has a tetrahedral electron arrangement and tetrahedral molecular arrangement, what will the bond angles be
109.5
86
how many valence electrons do nitrogen and phosphorus have
5
87
when distributing charge, should the charge go to the larger or the smaller atom
the larger atom
88
two types of covalent bonds
- sigma bonds
- pi bonds
89
T/F all hydrogen bonds will be drawn in bond-line drawings
false hydrogen bonds are understood if a carbon has less than four bond
90
what steric number will result in a tetrahedral electron arrangement
4
91
when woould an atom with a tetrahedral electron geometry (s# = 4) have a trigonal planarmolecular geometry
when there are three sigma bonds and 1 lone pair
92
what is the normal valence of phosphorus? when is it positive? negative
* 3 bonding pair and 1 lone pair
* 4 bonding pairs
* 2 bonding pairs and two lone pairs \*same as nitrogen
93
heteroatoms
atoms other than carbon and hydrogen in an organic compound
94
what is meant by the shape of the orbital
the region where an e- will be found 90% of the time
95
T/F psi value is indicative of charge
false, it indicates the position of the electron relative to the atom
96
what are the four possible molecular geometries in organic chem
tetrahedral, trigonal planar, bent, linear
97
what is the difference in shape between a unhybridized p and a hybridized sp orbital
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
* what function group is this?
* what are the restrictions on the R groups
* thiol
* can be C or H, but not C=O
99
* what type of functional group is this?
* what ran be the R group?
* a carboxylic acid
* it can be an C or H
100
what are the three types of hybridized orbitals? which has the highest energy
sp, sp2, sp3
the sp3 orbitals have the highest energy
101
T/F in an organic molecule, atoms will never have a charge greater than +/- 1
true
102
what is the normal valence of oxygen? when is positive? negative?
* 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
how to calculate formal charge
Fc = # of valence electrons - # of bonding pairs - # individual nonbonding electrons
104
alkane
a simple organic compound made of only of C an H with sigma bonds
105
what is the general formula for alkanes
CnH2n+2
106
how are alkanes classified
the longest number of consequtive carbons
107
what is the suffix for an alkane
ane
108
substituents
carbon atoms that are not part of the long carbon alkane
109
what suffix indicates a substituent alkane
-yl
110
methane, -yl
a single carbon alkane or substituent
111
ethane, -yl
a 2C alkane or substituent
112
propane, -yl
a 3C alkane or substituent
113
butane, -yl
a 4C alkane or substituent
114
pentane, -yl
a 5C alkane or substituent
115
hexane, -yl
a 6C alkane or substituent
116
heptane, -yl
a 7C alkane or substituent
117
octane, -yl
a 8C alkane or substituent
118
nonane, -yl
a 9C alkane or substituent
119
decane, -yl
a 10C alkane or substituent
120
what is added to ring shaped alkane
cyclo
121
T/F in the word cyclohexane, the H is used to alphabetize
false, the C is considered part of the word
122
how is an acyclic alkane named
* 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
when is a ring considered the parent of a molecule
when it has and equal or greater number of C as the longest chain
124
what is the structure of 3-ethyl-2methylhexane
a 6C chain with a 2C branch at 3 and a 1C branch at 2
125
when naming a molecule, in what order are the branches listed
alphabetically
126
what is the naming scheme when a molecule has a branch with substituents
the branch is placed in parentheses with the longest chain last
127
describe the structure of 3-(1-methylethyl)heptane
a 7C alkane with a 2C branch at 3, with a 1C substituent at 1
128
what is the naming scheme for halogen substituents (example)
is it alphabetical?
* the ine suffix is replaced with o (chloro, bromo, iodo, fluoro)
* alphabetical order still applies
129
what is the naming scheme when multiple identical substiuents come off the same branch
number prefixes are used
130
what are the number prefixes for multiple consituents
* di
* tri
* tetra
* penta
* hexa
* hepta
* octa
131
describe the structure of 2,2,5-tribromohexane
a 6C alkane with two bromines on 2 and one bromine on 5
132
T/F numbered prefixes for multiple branches are considered in alphabetical ordering
false
133
what alkane branches can have more than one name
* propyl
* butyl
* pentyl
134
when is a propyl group considered isopropyl
when the branch is attached to the middle C
135
what are the 3 possible names for a butyl group
* sec-butyl
* iso-butyl
* tert-butyl
136
sec-butyl
a 4C chain attached at C2
137
iso-butyl
a linear three carbon chain with a 1C branch that makes a Y
138
tert-butyl
a C with 3 methyl groups attached
139
1. tert-butyl
2. isobutyl
3. sec-butyl
140
two possible names for a pentyl group
iso pentyl and neopentyl
141
isopentyl
a 4C chain with a methyl group at C3 that makes a Y
142
neopentyl
a 3C chain with two methyl groups on C2 (looks like tert-butyl)
143
T/F prefixes iso/neo/sec/tert are not considered part of name and not used alphabetically
false
144
what is the arrangement of Rs in any primary functional group
2 Rs are H and 1 is C
145
what is the arrangement of R's in any secondary functional group
2 R's are C and 1 is H
146
what is the arrangement of R's in any teritary functional group
all 3 Rs are C
Organic Chem
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