O. Chem. Flashcards
1
Q
What are the 12 (1-12C) straight chain alkanes called
A
Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Undecane Dodecane
2
Q
What is the formula for straight chain alkanes
A
C(n)H(2n)+2
3
Q
What are the steps in naming organic compounds
A
- Find the largest carbon backbone
- Number the chain so the substituents are in the lower numbers
- Name the substituents
- Assign each substituent it’s carbon number
- List the substituents in alphabetical order (not counting the di,tri,tetra, sec, tert)(cyclo, iso and neo do count)
- Assign (cis, trans, R, S, Z, E)
4
Q
if there are two equally long carbon backbones, which one do you use for IUPAC naming
A
the more substituted one
5
Q
What is a t-butyl substituent
A
- C(CH3)3
6
Q
What is a neopentyl substituent
A
- CH2C(CH3)3
A t-butyl with a CH2 first
7
Q
What is an isopropyl substituent
A
- C(CH3)2H
8
Q
What is a sec-butyl substituent
A
An isopropyl with an extra carbon on one side
9
Q
what is an iso butyl substituent
A
an isopropyl with an extra carbon in front
10
Q
What do you do if there are more than one of a given substituent
A
use di-, tri-, tetra-
11
Q
How do commas and dashes work in IUPAC naming
A
commas between two numbers, dashes between words and numbers
12
Q
How do you start naming organic compounds where the largest carbon backbone is found in a ring
A
Assign C1 to be the MOST substituted carbon, and do the numbering so that the substituted carbons have the lowest numbers
13
Q
What are olefins
A
alkenes
14
Q
When double bonds are present how do you chose which carbon chain of equal length to use
A
the one with more double bonds (assuming it is tied for the longest chain with a double bond)
15
Q
so what happens if you have a carbon chain of 5 with a double bond, or a carbon chain of 6 without the double bond
A
you use the 5 C chain with the double bond as your backbone
16
Q
What does the term vinyl-mean
A
vinyl groups are monosubstituted ethylenes
17
Q
What does the term allyl mean
A
allyl groups are monosubstituted propylenes (at the C3 location)
18
Q
What is vinyl-chloride
A
a substituent ethylene with a chlorine at the C2 end
19
Q
What is acetylene
A
ethyne
20
Q
what is t-butyl bromide
A
C(CH3)3Br
21
Q
Which has priority when numbering a chain an alcohol, a double bond, or a triple bond
A
Alcohol has priority
22
Q
What are diols
A
molecules with 2 hydroxyl groups
23
Q
what are vicinal molecules
A
molecules with hydroxyl groups on adjacent carbons
24
Q
what are geminal molecules
A
molecules with 2 hydroxyl groups on the same carbon
25
What are ethers
ethers are 2 carbon chains that have an O inbetween them
26
what is an ether functional group called
alkoxy-
27
how are ethers named (IUPAC)
1. find the longest carbon chain with the ether
2. use the shorter chain as a substituent
3. number the ether
4. put -oxy- in before you name the carbon chain
28
how are common names of ethers derived
name the two alkyl groups in alphabetical order and add the word ether
29
What is an aldehyde
a carbonyl group with at least one H off of it
30
what is the suffix for aldehydes
-al
31
Where is the C1 in aldehydes
the carbonyl carbon
32
What is formaldehyde
methanal
33
What is acetaldehyde
ethanal
34
what is propionaldehyde
propanal
35
What is the suffix for ketones
one
36
how are ketones named
1. number the chain giving the ketone the lowest number possible
37
What is acetone
2 propanone
38
what is the suffix for carboxylic acids
- oic acid
39
where is the C1 for carboxylic acids
the carbonyl carbon
40
what is formic acid
methanoic acid
41
What is acetic acid
ethanoic acid
42
What is the suffix for amines
-amine
43
what is the substituent name for amines
amino
44
What do you do when a nitrogen is in the chain (like an ether)
you use N-(then name the shorter carbon substituent)
45
What are isomers
structures with the same molecular formula, but differ in structure
46
what are structural isomers
isomers with ONLY the same molecular formula
47
what are stereoisomers
isomers with the same molecular formula and connectivity
48
What are geometric isomers
compounds that differ in the position of substituents attached to a double bond
49
When do you use E or Z to name a double bond
when there are multiple substituents
50
how do you assign E and Z to double bonds
1. Find the highest atomic weight atom bonded to both sides of the double bond
2. if they are the same find the atomic weights bound to that one
3. if the higher priority are on the Zame Zide its Z
4. if the higher priority groups are on epposite sides its E
51
What is a chiral object
one that is not superimposable on its own mirror image
52
How do you assign R and S to stereocenters
1. Assign priority to the 4 groups based on atomic number
2. rotate it so #4 points away from you
3. If 1-2-3 is clockwise = R, if it is counterclockwise = S
53
what are the horizontal lines like in a fischer projection
sticking out of the page
54
enantiomers have identical chemical and physical properties with one exception...
optical activity
55
what does it mean when a compound is optically active
if it has the ability to rotate plan-polarized light
56
How is the rotation of light between two enantiomers related
they rotate light the same distance, but in opposite directions
57
what is an compound that rotates light to the right called
Dextrorotary (+)
58
What is a compound that rotates light to the left called
levorotary (-)
59
From which perspective do you assign directions to light rotation
from someone seeing the light approach them
60
What determines the amount of rotation caused by a compound to light
the number of molecules that the light wave encounters (concentration of the optically active compound and length of the tube through which the light passes)
61
what is the equation for specific rotation
```
specific rotation ([a]) =
observed rotation (a)/concentration*length
```
62
What is a racemic mixture
a mixture of equal parts of both the + and - enantiomers so that no optical activity occurs
63
how many possible stereoisomers are there for a molecule with n stereocenters
2n
| 5 stereocenters = 10 possible stereoisomers
64
What are enantiomers
nonsuperimposable mirror images
65
what are diastereomers
stereoisomers that are not mirror images
66
can enantiomers and diastereomers be seperated by physical means
no to enantiomers
| yep to diastereomers
67
What are meso compounds
a compound with chiral centers but has a plane of symmetry
not optically active
superimposable mirror image
68
how do you remember what meso compounds are
MeSo
| Mirror plane of Symmetry
69
What are conformaitonal isomers
compounds that differ only by the rotation about one or more single bond
70
What is the most stable conformation in newman projections
staggered or anti large groups
180 degrees away from each other
antiperiplanar
71
What is gauche in newman projections
the large groups are 60 degrees apart
| higher in energy than staggered conformation
72
What is eclipsed in newman projection
when the bond is rotated so that the front and back groups all overlap
73
what is totally eclisped in newman projections
when the two largest groups are overlapped
74
what is the order of energy in newman projections from lowest to highest of the different orientation
1. stagered (anti)
2. gauche
3. eclipsed
4. totally eclipsed
75
What are the three types of strain that influence cyclic conformations
angle strain
torsional strain
nonbonded strain
76
what shape do cyclobutanes take
a puckered shape
77
what shape do cyclopentanes take
envelope shape
78
what are the three types of shapes cyclohexanes take (in order of stability)
1. chair
2. boat
3. twistboat
79
which is more stable large groups axial or equitorial
equitorial
80
What is a node in atomic orbitals
locations where the probability of finding an electron in the orbital is 0
81
how many nodes do s orbitals have
0
82
how many nodes do p orbitals have
1
83
how many nodes do d orbitals have
2
84
what is a molecular orbital
when two atomic orbitals combine
85
When does a bonding orbital occur
when the signs of the wave functions are the same
| when they are opposite it creates a non-bonding orbital
86
what is a sigma bond
when two atomic orbitals overlap head to head
87
what is a pi bond
when two p-orbitals overlap in parallel fashion
88
What is a double bond (MO theory)
when both a sigma and a pi bond is formed between two atoms
89
What is a triple bond (MO theory)
when a sigma bond and two pi bonds are formed between two atoms
90
are pi bonds or sigma bonds stronger
sigma
91
are long or short sigma bonds stronger
short
92
what is an sp3
when one s orbital and 3 p orbitals are mixed to create 4 sp3 hybrid molecular orbitals
93
what is isobutane
C (CH3)3 H
94
What is neopentane
C(CH3)4
95
What is a primary, secondary, tertiary, and quaternary Carbon
```
primary = Bonded to 1 C
secondary = bonded to 2 C
tertiary = bonded to 3 C
```
96
What happens to boiling point, melting point, and density as chain length increases, and as branching increases
the longer the chain the higher the BP,MP, and Density are
| the more branching there is the lower the BP, MP, and density are
97
What is free-radical halogentation
the addition of a halogen by substitution
98
what are the steps of free radical halogenation
1. Initiation
2. Propagation
3. Termination
99
How does initiation happen
Diatomic halogens are cleaved by heat or light creating two radicals
100
What are radicals
species with unpaired electrons
| they are very reactive
101
How does propagation happen
1. The halogen radical reacts with an alkane, removing an H, Leaving a radical alkane
2. That radical alkane can react with a diatomic halogen creating an alkyl halide, and leaving another halogen radical
102
How does termination happen
two free radicals combine to form a stable molecule
| can be 2 radical halides, 2 radical alkanes, or one of each
103
Where does bromine attack during free radical halogenation
bromine replaces a H on the most substituted C, because it is the most stable place for the radical
104
Where does chlorine attack during free radical halogenation
because the reaction is so fast it happens it is fairly random between carbons.
105
What are combustion reactions
The reaction of alkanes with O2 to form
| H2O, CO2, and Heat
106
What is pyrolysis
the breaking down of a molecule by heat
107
what is another name for pyrolysis
cracking
108
What happens in pyrolysis
alkane C--C bonds are broken causing to alkyl radicals.
| those radicals combine to form all sorts of alkanes
109
what is disproportionation
when an alkyl radical transfers a H to another radical producing an alkane and an alkene
110
What are nucleophiles
electron-rich species that are attracted to positively polarized atoms
111
what determines how good a nucleophile is if it has the same attacking group?
if they have the same attacking group, nucleophilicity is roughly correlated to basicity.
RO- > HO- > RCO2- > ROH > H20
112
what determines how good a nucleophile is if it doesn't have the same attacking group
the bigger the atom, the better it is as a nucleophile
| CN- > I- > RO- > HO- > Br- > Cl- > F- > H20
113
what determines how good a nucleophile is in aprotic solvents
it is directly related to bascity
| F- > Cl- > Br- > I-
114
What determines the quality of leaving groups
weak bases make the best leaving groups
| I- > Br- > Cl- > F-
115
What is the mechanism of Sn1 reaction
1. dissociation of a molecule into a carbocation and a good leaving group
2. nucleuophilic attack on the carbocation
116
Where will Sn1 reactions occur the most
at the most substituted carbon
117
what is the slow step in an Sn1 reaction
the dissociation of a molecule into the carbocation
118
what determines the rate of Sn1 reactions
the concentration of the original molecule (not the concentration of the nucleophile
119
what things can increase the rate of Sn1 reactions
1. highly substituted carbons
2. highly polar-protic solvents
3. good leaving groups (weak bases)
120
What is the mechanism of an Sn2 reaction
1. nucleophile attacks the carbon opposite to the leaving group, bond strength shifts from the LG to the Nu. and the leaving group leaves
121
what does the nucelophile of an Sn2 reaction need to be like
strong and not sterically hindered
122
what determines the rate of Sn2 reactions
both the substrate, and the Nu
123
What order is an Sn2 reaction
2nd order
124
What does Sn1 reactions do to chirality
becuase it goes through a planar carbobation, it will produce two racemic products
125
What does an Sn2 reaction do to chirality
it keeps it chiral but flips it
126
what is the equation for finding double bond equivalents (degree's of unsaturation)
N = 1/2 (2n+2-m)
127
do cis or trans alkenes have higher boiling/melting point
trans-alkenes have a higher melting point (symmetry)
| cis-alkenes have a higher boiling point (polarity)
128
what is one physical difference between internal and external alkenes
internal alkenes have a higher boiling point than terminal (external boiling points)
129
What is another name for an E1 reaction
unimolecular elimination
130
what is the mechanism for E1 reactions
1. Leaving group leaves creating a carbocation
| 2. a base removes a proton and a double bond is formed
131
What determines the rate of E1 reactions
only the rate of the substrate (it goes through a carbocation intermediate)
132
What factors favor E1
1. highly polar solvents
2. highly branched carbon chains (more substituted)
3. good leaving groups
4. weak nucleophiles
133
How do you favor E1 over Sn1
with high temperatures
134
What factors favor Sn1 reactions
1. highly polar protic solvents
2. highly branched carbon chains (more substituted)
3. good leaving groups
4. weak nucleophiles
135
what is another name for Sn2 Reactions
bimolecular elimination
136
What is the mechanism for Sn2 Reactions
1. a strong base removes a proton, causing the anti halide to leave, resulting in a double bond
137
What kind of double bond is favored in an Sn2 reaction
more substituted
138
What situations favor E2 over Sn2
1. highly substituted carbon chains
| 2. Strong bases favor E2 (weak bases favor Sn2)
139
What are stereospecific reactions
reactions that favor one stereoisomer over the others
140
What are reduction reactions to a double or triple bond
reactions that add hydrogen atoms to get rid of one of the bond
141
what does H2 / Pd do
reduction by syn addition of two hydrogen atoms
142
What things attack and add to double or triple bonds
electrophiles
143
How do HX's add to double bonds
1. a hydrogen is added to the less substituted side and a carbocation + is on the more substituted carbon
2. then the X- adds to the + carbon on the carbocation
144
What is markovnikov's rule
that the carbocation is on the more substituted carbon, and the H+ adds to the less substituted side
145
how do X--X's add to double bonds
1. The double bond attacks the X, displacing an X-, and forming a cyclic halonium ion (three atom ring with the X at the top)
2. the X- then attacks from below the ring, and the two X's end up being added anti
146
What can happen when adding XX's to a double bond, in a nucleophilic solution
the nucleophiles can add during the final step and have only one X added`
147
When can water be added to alkenes
under acidic conditions (H+/H20)
148
What happens when water is added to alkenes in acidic condition
1. the double bond is protonated according to Markovnikovs rule creating a carbocation
2. the carbocation reacts with water, and the water loses it's proton
3. final product is an OH added to the most substituted carbon
149
what happens in free radical addition of a double bond that is different from most reaction
it doesn't follow markovnikov's rule because the most stable radical is formed, not the most stable carbocation
(the halogen is added to a the less substituted carbon
150
What is hydroboration of a double bond (BH3/THF)
When BH3 is added to a double bond, then it is typically replaced with OH by (H2O2/-OH)
151
How does hydroboration of a double bond occur
1. A transition state is created where BH2 begins to add to the less substituted side, while the H adds to the other (Syn)
2. The bond between the BH2 and H breaks and a syn anti-markovnikov product is formed
3. Oh replaces the BH2
152
What does potassium permanganate KMnO4 do to double bonds
That depends on if is in a cold dilute solution or a hot basic solution
153
What does potassium permanganate KMnO4 do to double bonds in cold dilute solutions
they produce syn 1,2 diols
| Oh is added to syn to both sides of the double bond
154
what does potassium permanganate KMnO4 do to double bonds is hot basic solutions
that depends on whether the alkene is terminal or not
155
what does potassium permanganate KMnO4 do to non-terminal double bonds is hot basic solutions
two molar equivalents of carboxylic acids are formed (Basically you cut the molecule at the double bond and create two carboxylic acids out of it, with the OH group where the double bond used to be)
156
what does potassium permanganate KMnO4 do to terminal double bonds is hot basic solutions
it will create a carboxylic acid and a CO2 molecule
157
What happens to a alkene that reacts with O3, CH2Cl2/(Zn/H2O)
the double bond is cleaved and turned into 2 carbonyls
| put two O's in the middle of the double bond and separate it
158
What happens to an alkene that reacts with O3, Ch2Cl2/NaBH4, CH3OH
the double bond is split, just like in the other O3 reaction, but then the carbonyls are reduced to OH groups
159
what happens when alkenes are reacted with CH3CO3H and MCPBA
an epoxide is produced where the double bond was
160
what is another name for an epoxide
Oxirane
161
How is polymerization done to alkenes
with a radical
162
What happens when an alkene is reacted with (radical carbon chain), heat, and pressure
polymerization from the monomeric alkene
163
How are alkynes created
reacting a di-anti halogenic alkane with heat and a strong base
164
What happens when a terminal alkyne is reacted with n-BuLi
1. the hydrogen is removed creating an acetylide ion
| 2. the acetylide ion acts as a nucleophile and does nucleophilic displacement of a alkyl halide
165
What happens when you react alkynes with
H2,Pd/BaSo4
--------------------->
quinoline (lindlars catalyst)
two hydrogens are added cis to each other, and a double bond is retained
166
What are the two ways to reduce an alkyne and keep a double bond
H2,Pd/BaSo4
--------------------->
quinoline (lindlars catalyst)
Na,NH3 (liq)
167
What happens when you react an alkyne with Na, NH3 (liq)
two hydrogens are added trans to each other and a double bond is retained
168
what happens when you add Br2 to an alkyne
Br's are added trans to each other and the double bond is retained. or if there is enough Br2, the reaction will proceed until Br2 was added to each side twice.
169
what happens in free radical addition to triple bonds
the X (radical) and H are added to take it down to a double bond. Results in the trans isomer.
170
What happens when an alkyne is reacted with BH3
1. syn addition of H and BH2 occurs
2. then the BH2 is replaced with an H by acetic acid
3. a cis double bond is the final product
171
what happens when a terminal alkyne is reacted with
R2Bh
-------->
H2O2, OH-
an Oh is added to the terminal end, an H is added to the other side. Double bond is retained.
then it can tautomerize into an aldehyde
172
What happens to alkynes reacted with
1) KMnO4, OH-
- --------------------->
2) H+
the triple bond becomes two carboxylic acids (the two carbons in the triple bond become the carbonyl carbons of the carboxylic acids)
173
What happens to alkynes reacted with
1) O3, CCl4
- ---------------->
2) H2O
the triple bond becomes two carboxylic acids (the two carbons in the triple bond become the carbonyl carbons of the carboxylic acids)
174
What is the electron rule for aromaticity
4n + 2 pi electrons in order for the molecule to be aromatic
175
what happens to aromaticity when you have $n pi electrons
you have an anti-aromatic structure (less stable)
176
What is toluene
a monosubstituted benzene with a CH3 group
177
what is phenol
a monosubstituted benzene with an OH group
178
what is analine
a monosubstituted benzene with an NH2 group
179
what is anisole
a monosubstituted benzene with an OCH3 group
180
What is benzoic acid
a monosubstituted benzene with an CO2H group
181
What is naphthalene
2 hooked benzene rings
182
what is anthracene
3 hooked benzene rings
183
what is pyridine
a benzene with a N(electron pair group in place of a C)
184
What is pyrrole
a 5 carbon ring, with two double bonds, and an NH(electron pair) group replacing one of the carbons
185
What happens when benzene is reacted with Br2 or Cl2 and FeCl3, FeBr3, or AlCl3
the benzene is halogenated once
186
what happens when benzene is reacted with F2 or I2
F2 usually leads to multisubstituted benzenes,
| I2 usually doesn't react
187
What happens when benzene is reacted with
SO3/H2SO4
-------------------->
heat
suflonic acid is formed
| SO3H is monosubstituted to benzene
188
What happens when benzene is reacted with
H2SO4
------------>
HNO3
NO2 is monosubstituted to benzene
189
what happens when benzene is reacted with a carbocation electrophile (carbonyl with a halogen) and a lewis acid (AlCl3)
Freidel-Crafts acylation
| the carbocaiton electrophile is added to benzene
190
What kind of directors are electron donating groups
activating, Ortho/para directors
191
What are some activators
NH2, NR2, OH, NHCOR, OR, OCOR, R
192
What kind of directors are weakly electron withdrawing groups
deactivating, Otrho/para directors
193
what are some examples of weakly withdrawing groups
F, Cl, Br, I
194
What kind of directors are strongly electron withdrawing groups
deactivating, meta directors
195
what are some examples of strongly electron withdrawing groups
NO2, SO3H, Carbonyl compounds (COOH, COOR, COR, COH)
196
What happens when benzene is reacted with
H2, RH/C
-------------->
100 C
The benzene is reduced to cyclohexane
| (can also be done with H2, Pd
197
what is m-cresol
an phenol with a methyl group added meta
198
what happens to boiling points of alcohol
they are higher than similar Hydrocarbons because they can H bond, this also makes them water soluble
199
What are the three reaction mechanisms for alcohol and ether reactions
1. Sn1/Sn2 nucleophilic substitution
2. Elecrophilic addition to a double bond
3. nucleophilic addition to a carbonyl
200
What is the oxidation/reduction continuum for primary alcohols
Primary alcohols aldehydes carboxylic acids
| reduction oxidation
201
What is the oxidation/reduction continuum for secondary alcohols
secondary alcohols ketones
| reduction oxidation
202
What happens in Sn1/Sn2 nulceophilic substitutions to alkyl halides
they can be turned into alcohols
203
What happens when an alkene is reacted with H2O
cis addition of H and OH
204
what happens to an carbonyl that is reacted with CH3MgBr
it is reduced to an alcohol
205
what happens when carbonyl groups are reacted with
1) LiAlH4
- ------------->
2) H3O+
They are reduced to form alcohols
206
What happens when carbonyl groups are reacted with
1) NaBH4
- -------------->
2) H3O+
The carbonyl group is reduced to form an alcohol
207
what is the difference in reduction between LiAlH4 and NaBH$
LiAlH4 is more powerful and can reduce carboxylic acids and esters, while NaBH4 can't
208
what happens when you add a para bromo analine to
HNO2
--------->
H2SO4
It turns into para bromo phenol
209
What happens when an alcohol is added to strongly acidic solutions (H2SO4)
it is dehydrated to alkenes
210
When alcohols are dehydrated in strong acid, what are the major and minor products
major = more substituted double bond
minor = less substituted double bond
(this is because the more subsituted went through a more stable carbocation)
211
is OH a good or bad leaving group
bad
212
what can be done to make OH a good leaving group
protonate it
convert it to tosylate
form an inorganic ester
213
What happens when you react an alcohol with HBr
the OH is protonated by HBr, then the Br- replaces the good OH2 + leaving group
214
What happens when you react an alcohol with tosyl chloride then NaI
the tosyl chloride reacts with the OH group making it a good leaving group, this is then replaced by I
215
What happens when you react an alcohol with SOCl2
The hydroxyl of the alcohol gets replaced by the Cl group
216
What happens when you react an alcohol with PBr3
The hydroxyl group of the alcohol gets replaced by Br
217
What happens when you react an alcohol with PCC
it converts primary alcohols to aldehydes
it converts secondary alcohols to ketones
it doesn't work on tertiary alcohols
218
What happens when you react an alcohol with
Na2Cr2O7
---------------->
H2SO4
it is oxidizes primary alcohols to carboxylic acids
| it oxidizes secondary alcohols to ketones
219
what happenswhen you react an alcohol with
CrO3, H2SO4
---------------------->
acetone
primary alcohols are converted to carboxylic acids
| secondary alcohols are converted to ketones
220
What is an ether
ROR
221
how are ether's named
small chain as the prefix, large chain as the suffix
| ____oxy_____
222
What is oxyethane
an 4 carbon ring with an O instead of a C
223
what is THF
a 5 carbon ring with an O instead of a C
224
how are ethers synthesized
reacting a metal alkoxide with a primary alkyl halide (becasuse for Sn2 to happen the alkyl halide cannot be sterically hindered)
225
what happens when you react RC-O- Na+ with R(1)-X
RC-O-R1 is formed via Sn2 (O- attacks R(1))
226
what happens when you react phenol and a primary alkyl halide with NaOH, H2O
you get a ether (phenol + alkane)
227
what happens when you react a alcohol with base and H+
you get internal Sn2, which forms an epoxide
228
what happens when you react a double bond with MCPBA
you get an epoxide formed
229
What is an ether
ROR
230
how are ether's named
small chain as the prefix, large chain as the suffix
| ____oxy_____
231
What is oxyethane
an 4 carbon ring with an O instead of a C
232
what is THF
a 5 carbon ring with an O instead of a C
233
how are ethers synthesized
reacting a metal alkoxide with a primary alkyl halide (becasuse for Sn2 to happen the alkyl halide cannot be sterically hindered)
234
what happens when you react RC-O- Na+ with R(1)-X
RC-O-R1 is formed via Sn2 (O- attacks R(1))
235
what is the prefix used when a ketone is a functional group
oxo-
236
what happens when you react a alcohol with base and H+
you get internal Sn2, which forms an epoxide
237
what happens when you react a double bond with MCPBA
you get an epoxide formed
238
What are peroxides, and how are they formed
they are ROOR's and they are formed by ethers reacting with O2 in the air
239
How is cleavage of ethers performed
in high temperatures, in the presence of HBr, or HI
240
which carbon is attacked in the opening of an epoxide
the more substituted C in the presence of acid
| the least substituted C in the presence of base
241
What is the product of axid-catalysed epoxide openin
OH and halide on opposite carbons
242
what is the product of base-catalysied epoxide opening
OH and halide on the same carbon
243
what is the prefix used when aldehyde is a functional group
formyl-
244
what is the prefix used when a ketone is a functional group
oxo-
245
what is more polar, alcohols or ketones and aldehydes
alcohols, since they can H-bond
246
What are the three ways to make aldehydes and ketones
1. oxidation of alcohols
2. Ozonolysis of alkenes
3. Friedel-crafts acylation
247
What is an enol
when a ketone loses an alpha proton, the proton attaches to the O, and the double bond switches place
248
what are tautomers
two isomers that differ only in the placement of a proton
249
What happens when Nitrogen containing compounds react with aldehydes and ketones
the NH2R becomes =NR and water is lost
250
What is the most common form of addition to carbonyl's
nucleophilic addition to the carbonyl carbon. (if there are no good leaving groups the O gets protonated and thats it)
251
What is hydration of a carbonyl
when H2O acts as an Nu and attacks the carbonyl carbon. final product is a diol.
252
What is an acetal/hemiacetal
a hemi acetal is when an alcohol Nu adds to a ALDEHYDE, making an ether.
an acetal is when it does so twice
253
what is a ketal/hemiketal
a hemi ketal is when an alcohol Nu adds to a Ketone, making an ether.
an ketal is when it does so twice
254
What happens when a ketone is reacted with ROH
once it makes a hemiketal, twice it makes a ketal
255
What happens when an ylide is reacted with a ketone/aldehyde
1. it Nu attacks the carbonyl Carbon
2. it forms a cylcobutane with P and O
3. double bonds are created (O=P, C=C)
256
What happens when you add NH3 to a ketone/aldehyde
the NH2 nu adds to the reaction, then H2O is lost, and an imine forms
257
what is an imine
when N is double bound to a C
258
What happens when Nitrogen containing compounds react with aldehydes and ketones
the NH2R becomes =NR and water is lost
259
what happens when an aldehyde/ketone is reacted with
Hg(Zn)
----------->
HCl
the carbonyl is removed
260
How is aldol condensation done
1. in a base the aldehyde is converted to it' enol form
2 the enol form Nu attacks another aldehyde and adds to it.
3. the O- gets protonated to form an aldol
261
what does the alpha carbon substituent do to the acidity of carboxylic acids
```
withdrawing groups ( Cl, NO2) increase acidity
donating groups ( NH2, OCH3) decrease acidity
```
262
What does the wittig reaction do
converts aldehydes and ketones into alkenes
263
what happens to the witting reagent
```
it starts out as (C6H5)3P
added to CH3Br
= (C6H5)3P+CH3
added to base
= (C6H5)3P=CH2
Resonance
(C6H5)3P+---CH2- (ylide)
```
264
What happens when an ylide is reacted with a ketone/aldehyde
1. it Nu attacks the carbonyl Carbon
2. it forms a cylcobutane with P and O
3. double bonds are created (O=P, C=C)
265
What happens when you have an aldehyde reacted with KMnO4, CrO3, Ag2O
it is converted into a carboxylic acid
266
What happens when you react an aldehyde or ketone with LAH or NaBH4
it is reduced to an alcohol
267
What happens when you react an aldehyde or ketone with H2NNH2 ( wolff-kishner)
the NNH2 replaces the O,
| in basic heated solutions the N2 will leave, and nothing will remain
268
what happens when an aldehyde/ketone is reacted with
Hg(Zn)
----------->
HCl
the carbonyl is removed
269
What can soaps do
solubilize nonpolar organic compounds in aqueous solutions becuase they have both a polar and a nonpolar end
270
What happens in Nu substitution in carboxylic acids
the Nu attacks and the negative O is formed just like normal. But then the OH is protonated and leaves when the C=O bond reforms
(simply the Nu replaces the OH)
271
what happens to the acidity of the H's in dicarboxylic acids
1. one carboxylic acid makes the other more acidic (electron withdrawing)
2. When that one loses it's proton, the - charge causes the 2nd carboxylic acid to be less acidic
272
where are beta dicarboxylic acids highly acidic
the alpha H's
273
what happens when you react aldehydes with KMnO4
you get a carboxylic acid
274
What happens when you react primary alcohols with KMnO4
you get a carboxylic acid
275
What is decarboxylation of a carboxylic acid
when a carboxylic acid loses CO2
276
what happens when you react an alkyl halide with
| HCN, then in basic or acidic solutions
1. the CN will replace the halogen
| 2. the RCN will then dissociate into a carboxylic acid and ammonia
277
How is soap formation done
reacting a long chain carboxylic acid with KOH or NaOH
278
What can soaps do
solubilize nonpolar organic compounds in aqueous solutions becuase they have both a polar and a nonpolar end
279
What happens in Nu substitution in carboxylic acids
the Nu attacks and the negative O is formed just like normal. But then the OH is protonated and leaves when the C=O bond reforms
280
what happens when carboxylic acids are reacted with LAH
they are reduced to aldehydes, then they can be reduced to alcohols
281
How are esters formed
when they react with alcohols in acidic conditions
282
What happens when carboxylic acids are reacted with primary alcohols in acidic conditions
the alcohol Nu attacks and replaces the OH group, forming an ester
283
What happens when you react SOCl2 with a carboxylic acid
you get an acid chloride
284
What is decarboxylation of a carboxylic acid
when a carboxylic acid
285
what happens when an acyl chloride is reacted with H2/Pd/ BaSO4 or quinoline
it is reduced to an alcohol or an aldehyde
286
what is the order of reactivity between acyl halides, esters, amides, and anhydrides
1. Acyl Halides
2. Anhydrides
3. Esters
4. Amides
287
what are the acyl halides
carboxylic acid derivatives where the Oh has been replaced by a halide
288
how are acyl halides names
-yl halide
289
what happens when carboxylic acids are reacted with SOCl2, PCl3, PCI5, or PBr3
an acyl halide is produced
290
What happens when an acyl chloride is reacted with water
it undergoes hydrolysis, recreateing the carboxylic acid
291
what happens when an acyl chloride is reacted with an alcohol
an ester is created
292
what happens when anhydrides are reacted with benzene and AlCl3
you get a benzoketone and an carboxylate anion
293
what happens when an acyl chloride is reacted with a benzene and AICI3
the benzene replaces the halide
294
What is an anhydride
R-C=O__O__O=C-R
295
what happens when an acyl chloride is reacted with a carboxylate salt
the salt attacks the acyl chloride, the chloride leaves, the C=O bond is restored, and an anhydride is created
296
what can happen when a dicarboxylic acid is heated
it can react to form a cyclic anhydride
297
what happens when anhydrides are reacted with water
2 carboxylic acids are formed
298
what happens when you react an amide with
| BrO- and then H2O
1) the Br adds to the N of the amide
2) the N loses it's H and forms water (nitrene)
3) the Br leaves, the N attaches to the R opposite (isocyanate)
4) the isocyante is hydrolized by H2O to make a primary amine and CO2
299
What happens when anhydrides are reacted with alcohols
an ester and a carboxylic acid are produced
300
what happens when anhydrides are reacted with benzene and AlCl3
you get a benzoketone and an carboxylate anion
301
What are amides
R-C=O__N-R__H (amino acid like)
302
How are amides named
1. -amide instead of -oic acid
| 2. anything attached to the N will be identified with the letter N
303
how are amides formed
1. reaction of acid chlorides with amines
2. Reaction of acid anhydrides with ammonia
(only primary and secondary amines work)
304
how is hydrolysis of amides done
in acidic conditions reacting with water
305
what is the hoffman rearrangement
amides are converted into primary amines
306
what happens when you react an amide with
| BrO- and then H2O
1) the Br adds to the N of the amide
2) the N loses it's H and forms water (nitrene)
3) the Br leaves, the N attaches to the R opposite (isocyanate)
4) the isocyante is hydrolized by H2O
307
what happens when an ester is reacted with CH3CH2MgBr (grignard)
one equivalent with bulky groups = a ketone
| more than one equivalent = tertiary alcohol
308
what is the suffix for esters
oate
309
how are esters synthesized
with alcohols and carboxylic acids (acid chlorides and anhydrides) under acidic conditions
310
what does hydrolysis of esters give you
an carboxylic acid and an alcohol
311
What is saponification
when fats (esters) as hydrolyzed under basic conditions to produce soaps.
312
What happens to soaps in acidic conditions
they are brought back to triacylglycerols
313
what are nitriles
C triple bonded to N
314
what is transesterificitaion
when an alcohol attacks an ester and just makes a new ester
315
What happens in claisen condensation
two ethyl acetates react in basic conditions to form
| 3-oxobutanoate
316
how is reduction of an ester done, and what does it produce
with LAH, and it produces two primary alcohols
317
what things have higher priority than amines in a carbon chain
OH and CO2H
318
what is the prefix/suffix for amine groups
-amine
| amino-
319
What are carbamates
they are esters with the other side of the carbonyl being an N group
320
how are nitro compounds reduced to primary amines
Zn
- ----->
dil. HCl
321
what is the boiling point of amines like
between alkanes and alcohols
322
why do tertiary amines have lower bp's than primary or seconday amines
they can't H bond
323
What is nitrogen inversion
when nitrogen flips inside out and back quickly
324
What happens when you react alkyl halides with NH3
the NH group replaces the Halide, then if you add it to base it becomes an alkylamine
325
What does gabriel synthesis do
converts a primary alkyl halide into a primary amine without creating side products
326
What is used in gabriel synthesis
o-phthalic acid (converted to phthalamide by NH3) Which is a good Nu
327
how are nitro compounds reduced to primary amines
with
Zn
------>
dil.HCl
328
What happens when you react RNO2 with
Zn
------>
dil.HCl
the NO2 becomes NH2
329
what is the product of the hoffman elimination (exhaustive methylation)
you get the least substituted double bond (not like normal)
330
how can you get a primary amine from a nitrile
LAH or H+ and a catalyst
331
how can you get a amine from an aldehyde or a ketone
1. react aldehyde or ketone with NH3 (NR2H, NH2R) to produce an imine
2. react the imine with H2-Ni (raney nickel) to produce an amine
332
What happens when you react an aldehyde or ketone with an amine, then H2-Ni (raney nickel)
you get an amine
333
how do you get an amine from amides
LAH
334
what happens when you react an amide with LAH
you get an amine
335
What is the hoffman elimination (exhaustive methylation)
1. you react an amine with Excess MeI (this methylates the NH2 to N(CH3)3
2. react this with Ag2O and H2O, then heat, and the N(CH3)3 group leaves and creates a double bond
336
what is the product of the hoffman elimination (exhaustive methylation)
you get the least substituted double bond
337
When is simple distialltion used
to separate liquids that boil under 150 degrees and at least 25 degrees apart
338
When is vacuum distillation used
to separate liquids that boil over 150 degrees and at least 25 degrees apart
339
When is fractional distillation used
to separate liquids that boil with less that 25 degrees of separation
340
what is unique about fractional distillations
it has a fractional column with inert objects of large surface area. the liquids condense and re-evaporate all the way up the column, this causes the lower boiling point one to make it to the top much quicker than the other
341
What is agarose gel electrophoresis
its when you use gel electrophoresis to separate DNA and RNA based on size. (because it is negative you don't need SDS)
342
What are epimers
carbs that differ in configuration at only one carbon
343
What is isoelectric focusin
a way to separate things based on charge
344
what are the four bond vibrations that occur
symmetric bending
asymmetric bending
symmetric stretching
asymmetric stretching
345
what causes absorption of energy in IR to be recorded
a change in the net dipole
346
what type of vibration doesn't show in IR
symmtetric stretches
347
Do O2, Br2 show up on Ir
nope (no dipole)
348
How do you know the difference between L and R carbs
if the last OH is on the left, then it is an L, if it is on the right, then it is a D
349
how do you draw cyclic versions of fisher projected carbs
things on the right will be pointing down, those on the left will point up
350
What are anomers
things that differ at the anomeric carbon
351
what are alpha anomers and beta anomers
alpha anomers point down (axial)
| beta anomers point up
352
which is more favored, alpha or beta anomers
beta (equitorial)
353
what happens when you react glucose with acid anhydride (CH3CO)2O and a base
all of the OH's become CH3CO2 groups
| esters
354
what is a reducing sugar
a monosaccharide with an OH on C1
355
What is oxidation of glucose do
converts C1 from CHO to COOH
| aldehyde to carboxylic acid
356
What happens when you react glucose with
Cu(OH)2
-------------->
benedict solution (tollens)
glucose C1 is oxidized from CHO to COOH
357
what happens when you react a hemiacetal (glucose) with an alcohol
you get an acetal (OR instead of OH) and a glycositic linkage
358
What is the linkage of cellulose
1,4 beta
359
what is the linkage of starch and glycogen
1,4 alpha (some 1,6 alpha)
360
What is the naturally occurring amino acid
L amino acids
361
What are the negative/acidic amino acids
aspartic acid
| glutamic acid
362
What does it mean that aminoacids are amphoteric
they can be acids or bases
363
What is the henderson hasselbach equaiton
pH = pKa + log [conjugate base]/[conjugate acid]
364
When are amino acid bufferers best
within one pH unit of it's pKa or pKb
365
What are the nonpolar amino acids
```
alanine
valine
leucine
isoleucine
proline
phenylalanine
glycine
tryptophan
```
366
What are the polar (uncharged amino acids)
```
Methionine
Serine
Threonine
Cysteine
tyrosine
asparagine
glutamine
```
367
What are the basic amino acids (+)
arginine
lysine
histidine
368
how are peptides formed
condensation reactions
369
how are peptides cleaved
hydrolysis reactions
370
where does trypsin cleave proteins
the carboxyl end of arginine and lysine
371
where does chymotrypsin cleave proteins
carboxyl end of phenylanlanine, tyrosine, and tryptophan
372
how are peptides drawn
from the N-terminal to the C-terminal
373
what is keratin made of
many alpha helices
374
how many AA's away are the bonds between AA's in alpha helices
4
375
What are silk fibers made up of
beta sheets
376
what is the difference between cysteine and cystine
cystine is two bonded cysteines
377
why doesn't proline fit into alpha helices
causes a kink
