Orgo I Flashcards
1
Q
aromatic
A
alternating single and double bonds
delocalized pi conjugated system
2
Q
nitrile
A
cyano
Carbon triple bonded to nitrogen
3
Q
Formal charge
A
The difference between the number of electrons in an atom’s valence shell in its ground state and the number assigned
valence electrons- bonds- nonbonded electrons
4
Q
epoxide
A
cyclic ether with a 3-atom ring
5
Q
what are the steps of alcohol dehydration
A
protonation of an alcohol with water, water leaves and forms a carbocation, OH- attacks carbocation and forms alkene
6
Q
Conformational isomers
A
when a molecule twists or rotates around its bond
known as a conformer
NOT TRUE ISOMERS- SAME exact molecule
7
Q
enamine
A
secondary amine condensed with alkene
8
Q
How can an alcohol form an alkene?
A
dehydration
9
Q
ester
A
derived from an acid with hydroxyl replaced by an alkoxy group
10
Q
Observed rotation
A
degree to which a sample rotates plane polarized light
11
Q
What characteristics make up an Sn2 reaction
A
substitution, bimolecular
reaction rate depends of the concentration of two species
12
Q
donor molecule
A
lewis base
13
Q
Bases
A
abstract protons
full or partial negative charge
14
Q
ketal
A
central carbon bonded to two -OR groups, two R groups
15
Q
sp3d2
A
octahedral
square pyramidal
square planar
90°
16
Q
meso compounds
A
molecules with two or more chiral centers that contain a plane of symmetry
17
Q
epimers
A
differ only at one chiral center
18
Q
by what mechanism is a 1° alcohol dehydrated?
A
E2
19
Q
E/Z convention
A
Prioritize the two constituents on each carbon by molecular weight
E- two higher priority on opposite sides of the double bond
Z- two higher priority on the same side of the double bond
20
Q
electrophiles
A
electron poor
partial or full positive charge
21
Q
rotation of plane-polarized light
A
enantiomers rotate plane-polarized light
22
Q
a triple bond has
A
one sigma and two pi bonds
23
Q
heat of combustion
A
total energy released as heat when a substance undergoes complete combustion with oxygen under standard conditions
24
Q
Huckel’s Rule
A
aromatic compounds must have exactly 4n+2 pi electrons
25
hydroxyl
-OH
26
polarimeter
apparatus that measures the rotation of plane-polarized light as it passes through a sample
27
racemic mixture
optically inactive mixture with 50:50 ratio of R:S
28
Do enantiomers contain a chiral center?
Yes
29
How many steps are in an Sn1 reaction?
two
30
what molecules does an Sn1 reaction favor?
poor nucleophiles, 3° carbons, polar protic solvents
31
are alcohols electro or nucleophilic?
nucleophilic
32
leaving groups
atoms or molecules that leave the parent molecule during a reaction
33
Relative configuration
spatial arrangement is identical but one non-identical substituent
34
-Ar is
benzene
35
Geometric isomers
cis/trans
36
Hybridization
mixing of atomic orbitals into new ones with different energies, shapes, etc suitable for the pairing of electrons to form chemical bonds
37
imine
contains a carbon nitrogen double bond
38
alcohol
organic compound with an -OH group
39
What characteristics make up an E1 reaction
elimination, unimolecular
| reaction rate depends on the concentration of the reactant only
40
are meso compounds optically active?
no
41
nucleophiles
attach carbons and central atoms
| full or partial negative charge
42
a single bond has
one sigma bond
43
Is alkane synthesis syn or anti addition?
syn
44
nitro
NO2
45
Acetyl
methyl group single bonded to a carbonyl
46
are nucleophiles a function of thermodynamics or kinetics?
kinetics
47
Do alcohols have a higher or lower BP/MP than alkanes? why?
higher, hydrogen bonding
48
How can the opening of an epoxide ring occur?
Sn1- protonation of O, opening of ring as the nucleophile attacks carbon, base abstracts proton
Sn2- nucleophile attacks carbon as the ring opens and the oxygen is protonated
49
Syn addition
two new bonds formed on the same side
50
Electronegativity of O
2.5
51
Pi bond
formed by side to side overlap of two p orbitals
52
what conformation of cyclohexane has zero ring strain
chair conformation
53
VESPR
Predicts the shape molecules will take due to the repulsion of lone pairs of electrons
54
grignard
R-MgBr
55
bond strength
measures of the energy required to completely break two atoms apart
56
what molecules does an E1 reaction favor?
weak bases, 3° carbons, polar protic solvents
57
Resonance
structures that are two forms of a molecule where the chemical connectivity is the same but the electrons are distributed differently around the structure
58
alkoxy
alkyl group single bonded to oxygen
| R-O
59
How do R and S differ in the ways that they rotate plane polarized light?
same degree, opposite directions
60
MOM
methoxy-methyl ether
61
step 1 of an E2 reaction
abstraction of a proton by a base with the collapse of the electrons to an alkene and ejection of the leaving group
62
benzyl
benzene attached to a carbon
63
recipient molecule
lewis acid
64
protection of alcohols can be achieved with what?
```
trimethylsilyl ether (TMS)
methoxy-methyl ether (MOM)
```
65
what direction to electrons flow?
negative to positive charge
| bases/nucleophiles attach electrophiles
66
isomers
two molecules that have the same molecular formula but are different compounds
67
hydrazine
H2N-NH2
68
aliphatic
carbons form open chains
69
what are the products and reactants in a grignard synthesis?
carbonyl and grignard form an alcohol
70
vertical lines on a fischer projection
into the page
71
hemiacetal
acetal with one -OR group replaced with -OH
72
anomeric carbon
c-OH next to the oxygen of a ring
73
what alkanes have the highest melting points
straight chain
74
Dipole Moment
any time charge is not evenly distributed within a bond (nonequal electronegativities)
75
sp3d
```
trigonal bipyramidal
seesaw
T-shape
Linear
120° and 90°
```
76
how can protecting groups be removed?
acidification
77
ether
r-o-r
78
aldehyde
organic compound containing formyl
79
Vinyl
ethylene with one H replaced by another atom (halogen)
80
mesyl
salt/ester of methanesulfuric acid H3C-SO3
81
anhydride
two acyl groups bonded to the same oxygen
82
Maximum optically active stereoisomers
2^n
| n- number of chiral centers
83
Amine
derived from ammonia with hydrogen replaces by an organic group
84
How many steps are in an E1 reaction?
two
85
How can an alcohol be formed from a ketone or aldehyde?
reduce
86
acetal
central carbon bonded to two -OR groups, one R group and a hydrogen
87
step 1 of an E1 reaction
leaving group leaves, carbocation forms
88
Electronegativity
measure of the tendency of an atom to attract a bonding pair of electrons
89
Lowest electronegativity
Fr
90
sp2
trigonal planar
bent
120°
91
are arrows drawn towards or away from an electrophile?
towards
92
step 1 of an Sn1 reaction
dissociation of the leaving group forming a carbocation
93
specific rotation
observed rotation divided by length and concentration
94
-Ph is
benzene
95
levorotary
rotates plane polarized light counterclockwise
96
sp
linear
| 180°
97
does the BP/MP of an alkane increase or decrease with branching?
increase
98
what happens when you combine an alcohol with HCl?
formation of an alkyl halide
99
what are the reactants and products of the pinacol rearrangement?
vic-diol to an aldehyde or ketone
| acid catalyzed
100
Exceptions to the octet rule
H/He stable with two valence electrons
B/Be stable with six valence electrons
Third period or higher stable with expanded octets
101
sp3
tetrahedral
trigonal pyramidal
bent
109.5°
102
Highest electronegativity
F
103
octet rule
atoms gain or lose electrons to obtain exactly 8 electrons in their valence shell
104
dextrorotary
rotates plane polarized light clockwise
105
How many steps are in an E2 reaction?
one
106
stereoisomers
same formula, same bond-to-bond connectivity, different in the 3D arrangement of the substituents
107
anti addition
two new bonds are formed on opposite sides
108
How many steps are in an Sn2 reaction?
one
109
axial
rise vertically
110
Structural isomers
same formula, different bond-to-bond connectivity
111
hemiketal
ketal with one -OR group replaced with -OH
112
what molecules does an Sn2 reaction favor?
good nucleophiles, 1/2° carbons
113
what are the steps of the pinacol rearrangement?
vic-diol plus acid protonates -OH to -OH2+ and water leaves forming a carbocation, methyl shifts are possible
resonance with the OH and carbocation to oxygen double bond and removal of H to a ketone or aldeyhde
114
name three reducing agents
NaBH4
LiAlH4
H2 and pressure
115
horizontal lines on a fischer projection
out of the page
116
Alkene
at least one c-c double bond
117
What happens when a 3° alcohol is combined with an oxidizing agent?
no reaction
118
Electronegativity of F
4
119
how do you synthesize an alkane from an alkene
H2 and a metal catalyst (Pd)
120
Which is stronger, a sigma or pi bond? why?
sigma bond because they have more overlap
121
actual structure
weighted average of all resonance contributors
more stable structures contribute more
122
Electronegativity of H
2.2
123
name three common oxidizing agents
```
O3
Cr2O7
CrO4
KMnO4
PCC
PDC
Collins
Jones
```
124
are alcohols more or less acidic than water?
less
125
What happens when a 2° alcohol is combined with an oxidizing agent?
ketone
126
absolute configurations
R and S
assign priority to all substituents based on molecular weight, rotate lowest priority to the back
clockwise 1-3: R
counterclockwise 1-3: S
127
step 2 of an Sn1 reaction
attack of carbocation by the nucleophile
128
what can be used to reduce an acid or ester
LiAlH4
129
bonds broken and reformed via radical reaction
combustion
130
chiral center
atom attached to four different substituents
131
How does an alkyl halide form from an alcohol?
Sn2 or Sn1
add acid with halide to protonate alcohol, loss of -H2O and attack of carbocation or molecule by the halide to form alkyl halide
132
Allyl
methylene bridge attached to a vinyl group
133
-C6H5 is
benzene
134
what groups are electron donating?
negative
135
Alkyne
at least one c-c triple bond
136
TMS
trimethylsiyl ether
137
by what mechanism is a 2/3° alcohol dehydrated?
E1
138
What molecule reacts with an alcohol to form R-Cl
SOCl2
139
(+)
dextrorotary
140
Sigma Bond
Formed by head-on overlapping between atomic orbitals
141
Alkane
all c-c and c-h single bonds
142
vicinal
bonded to adjacent atoms
143
What happens when a 1° alcohol is combined with an oxidizing agent?
aldehyde, carboxylic acid
144
sulphone
SO2 attached to two carbons
145
Single bond is a
sigma bond
146
Amide
nitrogen single bonded to C of carbonyl
147
aromaticity
cyclic or planar molecule with a ring of resonance bonds that exhibits more stability than other geometric arrangements with the same set of atoms
148
Coordinate covalent bonds
both electrons shares in the bond are donated by one atom
149
anomers
differ only in their spatial orientation at the anomeric carbon of a ring
150
equatorial
extend horizontally
151
what does the opening of an epoxide form?
alcohol
152
what molecules does an E2 reaction favor?
strong or bulky bases
153
acyl
alkyl group with a carbon double bonded to oxygen
154
aryl
aromatic ring with one H removed
155
step 2 of an E1 reaction
base abstracts H from carbocation molecule and alkene forms
156
what are the steps in a grignard synthesis?
grignard attacks a carbonyl, acid donates a proton to O- forming an alcohol
157
does the BP/MP of an alkane increase or decrease with molecular weight?
increase
158
Geminal
bonded to the same atom
159
the second and third bonds between two elements are
pi bonds
160
step 1 of an Sn2 reaction
back side attack of the electrophile with simultaneous ejection of the leaving group
161
What characteristics make up an E2 reaction
elimination, bimolecular
| reaction rate depends of the concentration of two species
162
ketone
carbonyl group bonded to two hydrocarbon groups
163
What groups are electron withdrawing?
positive
164
are bases a function of thermodynamics or kinetics?
thermodynamics
165
Enantiomers
stereoisomers that are non-identical, non-superimposable mirror images of one another
166
are alkenes electro or nucleophilic?
nucleophilic
167
tosyl
methyl group para substituted on benzene to SO3-R
168
Electronegativity of Fr
0.7
169
How is a tosylate/methylate formed?
tox/mes-Cl reacts with an alcohol, Cl- leaves and removes H from the molecule to form HCl and tos/mes-OR
170
carbonyl
carbon double bonded to oxygen
171
VESPR stands for
valence shell electron pair repulsion theory
172
valence
number of bonds an atom "normally" makes
173
Less stable bonds have ____ heats of combustion
higher
174
Carboxylic Acid
organic acid containing COOH
175
a double bond has
one sigma and one pi bond
176
Which atom is partially positive in a nitro group
nitrogen
177
(-)
levorotary
178
example of coordinate covalent
iron in hemoglobin
179
What molecule reacts with an alcohol to form R-Br
PBr3
180
Alkyl
hydrocarbon radical from removal of a hydrogen
181
dipole moment (u)=
charge*distance
| distance between charges
182
What characteristics make up an Sn1 reaction
substitution, unimolecular
| reaction rate depends on the concentration of the reactant only
183
Diastereomers
two molecules with the same formula and bond-to-bond connectivity that are non-identical but are not mirror images
