O-Chem Deck Flashcards
1
Q
Haloform; CH3, methyl ketone
A
*I2, excess, OH- is the … reaction. It removes a … from a …
2
Q
dextrorotatory; levorotatory; S
A
+ Rotation = …; - Rotation = … If you have an R enantiomer, it’s mirror image will be …
3
Q
Carbonyl, an Alcohol
A
… appears around 1720 cm^-1, … gives a broad signal around 3300 cm^-1
4
Q
Tollens; acid
A
1) Ag2O, NH3 2) H3O+ is the … reagent. It will oxidize an aldehyde into an …
5
Q
aniline (NH2)
A
1) Sn, HCl, 2) OH- react with a Nitro (NO2) group on a benzene ring and make
6
Q
Zwitterion, Amino Acids
A
A … is a molecule that has both a positive and negative electrical charge on different atoms within the molecule. They are commonly found in …
7
Q
*Alkyl and Allylic Halides= Positive in AgNO3 in alcohol *A precipitate of AgX is formed
A
A chemical lab test using AgNO3 in alcohol is used to test for … and … A precipitate of … is formed.
8
Q
*Chromate oxidations= Primary and Secondary alcohols are oxidized. *Reddish-orange dichromate gives a greenish solution, same as Jones oxidation.
A
A chemical lab test using Chromate oxidations is done with … The reddish-orange dichromate or chromate agent shows a … solution. … oxidation gives the same result.
9
Q
70% R + 30% R+S (racemic) = 85% R, 15% S
A
A compound is 70% pure R, the it’s entire composition is …
10
Q
Polarimeter
A
A device used to measure the effect of plane-polarized light on optically active compounds is called a
11
Q
Double bond or ring contributes: 1 degree of unsaturation Triple Bond contributes: 2 degrees of unsaturation
A
A double bond or ring contributes … degrees of unsaturation, a triple bond contributes … degrees.
12
Q
a primary amine
A
A Gabriel Synthesis is a simple SN2 mechanism in which a primary alkyl halide is converted into …
13
Q
*Alkenes, alkynes and alcohols dissolve when added to cold H2SO4 *Alkanes and alkyl halides are insoluble
A
A lab test with concentrated H2SO4 dissolves … Other substances such as … are insoluble.
14
Q
optical activity, chiral carbons, a plane of symmetry
A
A meso compound has no …, it does however contain … and …
15
Q
greatest
A
A molecule that is branched and possesses symmetry can fit into a crystal best, thus has the … melting point.
16
Q
highest, greatest, greatest, lowest
A
A molecule with no branching will have the … boiling point, … amount of surface area, … amount of dispersion forces and the … melting point.
17
Q
2200 cm^-1
A
A Nitrile, CN (triple) bond would give an IR band at
18
Q
mutarotate, negative, negative, NO hemiacetal group
A
A Non-Reducing sugar will not …, give a … Tollens test, a … Benedicts test and will not contain a … group.
19
Q
Zwitterion
A
A nuetral form of an amino acid such that it is equally protonated and equally deprotonated is called a
20
Q
Amino group, Carboxy group
A
A peptide bond or amide bond is formed between the … of one amino acid and the … of another amino acid.
21
Q
Tollens (+)= aldehyde; alpha-hydroxy ketone 2,4 DNP (+)= carbonyl group
A
A positive Tollen’s test suggests either … or … A positive test with 2,4-DNP suggests a … group.
22
Q
polypeptide subunits.
A
A proteins quaternary structure is the arrangement of …
23
Q
the 3-D shape, Fibrous proteins; collagen sheets/long strands
A
A proteins tertiary structure is …, examples include …
24
Q
centrifugation, the bottom
A
A red blood cell in plasma is best separated by … in which the more dense particles settle towards …
25
*Ag(NH3)2OH= this is a test for alkynes with terminal triple bonds
A silver nitrate in ammonia *Ag(NH3)2OH* chemical lab test was performed to test for ...
26
raise
A soluble nonvolatile substance such as NaCl will ... the boiling point.
27
*Tollens Test- primarily for Aldehydes, uses Ag(NH3)2 or Ag2O/ NH3 *The reaction flask is coated with a "mirror of silver" Remember **Positive Tollens Test also means a reducing sugar, that will mutarotate, and give a positive Benedicts Test
A Tollens test is primarily a test for ... using ... For a positive result, the walls of the reaction flask are coated with a "...
28
high
Alcohols have hydrogen bonding which increases the intermolecular forces of attraction which gives rise to a ... boiling point.
29
an Amino group, a Carboxyl group, and a variable R-group side chain
All amino acids contain (3 things)
30
deactivate
All meta directors ... the ring
31
not be, protonation by acqeuous acid, ammonium salt.
Amines larger than 3 carbons will ... water soluble. Amines become soluble by ..., which converts the Amine into a water soluble ...
32
Amide
An acyl halide reacts with a primary amine to yield?
33
an Anhydride.
An acyl halide reacts with an acid (COOH) to form ...
34
an alpha hydrogen, remove, the alpha hydrogen, an enolate anion
An Aldol Condensation reaction can only occur if the aldehyde or simple ketone involved contains ... because we must ... the ...in order to generate ....
35
1650 cm^-1
An alkene would give an IR band at
36
2200 cm^-1
An alkyne would give an IR band at
37
1700 cm^-1
An anhydride would give a pair of bands around
38
1200 cm^-1
An ether would give an IR band at
39
separation, isolation
An extraction with solvents is used for ... and ... of substances from mixtures.
40
*Iodoform Test I2/OH-: Positive for a methyl ketone, or methyl carbinol. *A yellow precipitate of CH3I (iodoform) forms
An Iodoform I2/OH- chemical lab test was used to test for ... A ... precipitate of ... formed.
41
Fatty Acid; fatty acids contain long hydrocarbon chains and a single acid group C14H28O2= CH3(CH2)12COOH
An unknown compound was identified as C14H28O2. This compound is likely a:
42
cyclic, planar sp2 hybridization/ p-orbitals Huckel's Rule: 4n + 2 pi electrons.
Aromatic compounds must be ..., planar, with every atom of the ring having ..., while obeying Huckel's Rule of ...
43
unreactive
Aryl halides (aromatic) and vinyl halides (double bonds) are ... in both SN1 and SN2 reactions.
44
1-4 addition, thermodynamic
At high temperatures a conjugated diene will give the major product as ..., this is under ... control.
45
1-2 addition, kinetic
At low temperatures a conjugated diene will give the major product as ..., this is under ... control.
46
negative, it doesn't contain a true double bond, but rather a resonance hybrid.
Benzene gives a ... test in Br2/CCl4 and cold dilute KMnO4 because ...
47
double or triple bonds; colorless, brown
Br2/CCl4 and cold, dilute KMnO4 react with compounds containing ... For this test orange/brown Br2/CCl4 becomes ... and purple KMnO4 turns ...
48
lowers, surface area
Branching ... the boiling point of a molecule because branched molecules have less ...
49
3300 and 3400 cm^-1 due to the two H's attached to the N.
CH3CH2NH2 will contain two weak absorbtions at approximately ... and ... due to the ...
50
Epoxidation occurs
CH3COOOH reagent indicates that ...
51
Baeyer-Villiger reaction, an ester
CH3COOOH reagent indicates the ... reaction. An aldehyde or ketone is converted into ...
52
oxidize, acids
Compounds such as Ag(NH3)2+ (tollens reagent) or Ag2O are mild agents used to ... aldehydes into ...
53
axial, equatorial
Consider (trans)-1-bromo-3-methylcyclohexane. The most stable conformation is given when bromine is ... and methyl is ...
54
Column chromatography and Crystallization can be used to seperate two isomers. First a mixture is dissolved in ethanol and cooled, the para isomer will crystallize out, and the ortho isomer will not. Crystals are then isolated and the mother liquor is run through a column to purify the ortho isomer.
Consider p - Nitroaniline and o - Nitroaniline. What methods are used to seperate these two compounds?
55
tautomers
Constitutional isomers that co-exist in rapid equilibrium are called
56
syn-same face; also it adds in the direction that creates the least steric hindrance.
D2 , like H2 simply adds across a double bond in a ... fashion.
57
random coil
Denaturation causes a protein to lose its structure and revert to ...
58
Epimers
Diastereomers in which two molecules differ in configuration about one carbon are called
59
water, 5 or 6 membered ring. *See #235 if unclear, Destroyer 2011*
Dicarboxylic acids can readily lose ... when heated if they can form a ...
60
different, different
Different bonds vibrate at ... frequencies, thus they absorb ... frequencies of IR light.
61
2', deoxyribonucleic acid, outside the helix, interact with water.
DNA lacks a ... OH group, it is a ... acid. The sugar and phosphate groups lie ... where they are able to ...
62
*Alkenes and Alkynes = Positive in dilute KMnO4 *Deep Purple KMnO4 turns brown
During a chemical lab test using dilute KMnO4 ... give a positive test and cause deep purple KMnO4 to turn ...
63
*Alkenes, alkynes = Positive test in Br2/CCl4 *The orange brown color decolorizes
During a chemical lab test with Br2/CCl4 ... give a positive test, in which the orange/brown color of Br2/CCl4 ...
64
last, first
During column chromatography the order of elution depends on the polarity of the molecule. The most polar molecules elute ... and the least polar molecules elute ...
65
Wittig= (:P(Ph)3+ with an alkyl group) Ph= phenyl/ benzene ring
During the ... reaction we synthesize an ylide.
66
FeBr3
During the Bromination of Benzene, which catalyst is employed?
67
*trans: highest priority substituents are opposite *cis: highest priority substituents are on same side
E means ... Z means ..
68
Carbocation intermediate, Rate Law; 1st order k[halide], both are favored by tertiary substrates, since tertiary halides form tertiary carbocations
E1 and SN1 both share (3 properties)
69
increase, decrease; strongly acidic
EWG's ... acidity, ERG's ... acidity. A ring with an ERG and an EWG para to one another is ...
70
CN, SO3H, COOH, CF3, NO2, aldehydes, carbonyls
Examples of meta directors are: (5-specific)
71
OH, CH3, C2H5, C3H7, OCH3, OC2H5, NH2, NO, Halogens
Examples of ortho-para directors are: (5 in general)
72
exothermicity, fast, endothermic, slowest. Remember: F2> Cl2> Br2> I2 for radical reactions.
F2 has a very high ... in propagating steps and reacts very ... I2 has a very ... first propagating step, thus reacts the ...
73
unsaturated fatty acids, -fish=good=unsaturated
Fish and plant oils are abundant in
74
Ketones: O is inserted closest to the most branched/ substituted portion of the molecule closest to the Carbonyl group. Aldehydes: Insert the O closest to the Hydrogen atom
For a Baeyer-Villiger reaction (CH3COOOH), if given a ketone, insert the O closest to the ... If given an aldehyde insert the O closest to the ...
75
5 or 6 membered rings, always a di-beta-ketoester
For a Claisen-condensation reaction, a diester is treated with strong base (-NaOC2H5) to yield ...
76
stablizing the carbocation transition state
For SN1 polar protic solvents such as H2O and CH3OH are best because they accelerate the reaction by ...
77
tertiary; 3>2>1
For the SN1 reaction, the reactivity is faster for ...halides
78
Acidic Protons; hinder its formation; an acidic proton
Grignards are powerful bases, they react with ... Groups such as SH, OH, COOH, NH2 and alkynes would react with Grignard and ... A species would react the quickest when it doesn't contain ...
79
poor, not be displaced
Groups such as OCH3, OH, CN, OC2H5 are ... leaving groups and would ... by nucleophiles such as I-
80
Anti-Markovnikov
HBr and ROOR adds the Br group
81
Markovnikov, ROOR only works Anti Markovnikov with HBr
HCl and ROOR will simply add ... ROOR, will only work with
82
loss of CO2; decarboxylation
Heating a Beta-keto acid will result in ...
83
basic extraction
Hexanoic acid can be seperated from a mixture by
84
lower, fluid-like, kink, tightly packing
If a double bond is present, we have a ... melting point unsaturated fatty acid that tends to be ... A double bond produces a "... in the molecule and prevents it from ...
85
positive Tollens test, positive Benedicts test, mutarotate, reducing sugar.
If a hemiacetal group is present, a molecule can open up to its free aldehyde group, give a ... Tollens test, a ... Benedict's test, ... and be classified as a ...
86
Up= Beta; Down= Alpha
If OH is up at C-1 the sugar is ... If OH is down at C-1 the sugar is ...
87
Up= D-sugar, it will also mutarotate Down= L-sugar
If the highest numbered carbon molecule is pointed up, the molecule is considered a ... sugar. If the highest numbered carbon molecule points down, it is a ... sugar.
88
alpha form, beta form, alpha and beta forms differing in 1 Carbon are related as anomers
If the OH group at C-1 is down, we call it ... If the OH group at C-1 is up, we call is ... These two forms are related as ...
89
fractional distillation
If two compounds boil within a few degrees of one another, a ... would be a likely technique for separation.
90
axial, equatorial, 1-3 diaxial interactions, depart readily.
If you do elimination on a cyclohexane ring, draw a chair conformation first. Remember, the H and the halogen must both be in the ... position. If t-butyl is present it must be in the ... position. By placing a group in the equatorial position we minimize ... and atoms can ...
91
slowly, longer it will take to elute
In column chromatography the more polar a compound is, the more ... it will travel and the ... it will elute.
92
Elution
In column chromatography, a mixture is placed at the top of a solid support. The motion of the solute and solvent through the solid phase is called
93
polar, polar, non-polar
In column chromatography, the silica gel is ... and attracts ... molecules, while the ... molecules that do not strongly attract will elute first.
94
A-T= 2H bonds, G-C=3H bonds, melting point increases and stability of sample increases.
In DNA A-T forms ...bonds and C-G forms ... bonds. As we increase the % GC, we increase the ... and ... the stability of the DNA sample.
95
high enegry electrons, fragment
In mass spectrometry, a molecule is bombarded with ..., which may ... the molecule.
96
*Clemmenson Reduction: Zn(Hg), HCl *Wolff-Kishner Reduction: NH2NH2, OH- , heat.
In order to completely transform a carbonyl on a benzene ring into CH2, we use ... or ...
97
finding the nearest alkane and subtracting the difference in H's, and dividing that number by 2 to find degree of unsaturation.
In order to find how many double bonds a molecule contains we have to find the "degree of unsaturation". We do this by ...
98
I- > Br- > Cl- > F-
In terms of the Halogens (Group 17), what is the correct order from best leaving group to worst leaving group?
99
short, polar, soluble
In thin layer chromatography compounds with small Rf values travel ... distances are most ... and most likely to be ... in water.
100
nonpolar, furthest
In thin layer chromatography the compound with the greatest Rf value is most ... and travels the ...
101
inversely, faster
In thin layer chromatography, migration distance is ... proportional to molecular weight, thus heavier molecules travel ...
102
dipole, symmetry (trans componds)
IR absorption occurs when a molecule has a ..., when there is ... there is a weak IR signal.
103
identify molecular structure
IR spectroscopy is a technique used to
104
aldehydes> primary alcohols ketones> secondary alcohols esters> primary alcohols carboxy acids> primary alcohols no effect on double and triple bonds
LiAlH4 reduces aldehydes into ... ketones into ... and carboxy acids into ... It has ... effect on double and triple bonds.
105
removing the alpha proton that is most accessible/ least sterically hindered.
Lithium diisopropylamide (LDA) is a large, sterically hindered base that reacts by ...
106
zero, plane of symmetry- which makes them optically inactive
Meso compounds have a rotation of ... since they contain a ...
107
primary alcohols, secondary alcohols; Unlike LiAlH4, NaBH4 will not react with acids (COOH), esters or nitriles
NaBH4 is a reducing agent that will reduce aledhydes into ... and ketones into ... However it will not react with ...
108
NH2, Diazonium Salts *Remember* 1) Sn, HCl : transforms NO2 into NH2 2)OH-
NaNO2, HCl-> followed by H3PO2 are used to completely remove ... from a benzene ring in ....
109
activate; deactivate
Ortho-para directors ... the ring, but when it comes to NO and Halogens they ... the ring.
110
primary alcohols= aldehydes secondary alcohols= ketones
PCC is a mild oxidizing agent that oxidizes primary alcohols into ... and secondary alcohols into ...
111
oxidize, ketones
PCC will ... secondary alcohols to form ...
112
OH groups, aldehydes or ketones
Periodic acid or HIO4 will cleave ... on adjacent carbons and oxidize them into ...
113
polymer through polymerization
Peroxide initiators simply allow for the formation of a
114
imines; enamines
Primary amines react with aldehydes and ketones to form ... Secondary amines react to form ...
115
Aldol Condensation
Propanal and dilute sodium hydroxide react by this mechanism
116
Bronsted-Lowry acid; Bronsted-Lowry base it is accepting a proton.
Propyne is donating a proton to -:NH2; Propyne is acting as the ... and -:NH2 is the ... since ...
117
Amino acid sequence
Protein's primary structure
118
Alpha-helix, Beta-pleated sheets
Proteins secondary structure is the local structure of a protein as determined by Hydrogen bonds. Examples include
119
Oxygen, or a Carbonyl Oxygen
Protons are most acidic when they are attached directly to
120
larger, electronegative, loosely held, better
S is ... than O, less ... than O, thus it is more polarized, meaning electrons are more ..., this makes S a ... nucleophile.
121
filtration
Sand can be seperated from a mixture by
122
insoluble, no effect
Sand or charcoal are ... substances, they will have ... effect on boiling point.
123
animal fat. -Remember fat=bad=saturated
Saturated fatty acids are abundant in ...
124
most stable
SN1 reactions occur fastest for the ... carbocation
125
polar aprotic
SN2 works best with ... solvents
126
experimentally determined
Some R molecules are + and some are -, the same goes for S molecules. This property is ...
127
E2
Strong bases such as C2H5O-Na+ and CH3O-Na+ favor ... reactions when reacted with tertiary halides.
128
*non-reducing sugar; also gives a negative Tollens test, negative Benedict's test, does not mutarotate. * Glucose + Fructose -> Sucrose, they are linked by Glycosidic Linkages
Sucrose does not contain a hemiacetal group, thus it is a ... The linkage seen in the sucrose molecule is called ...
129
glucose, fructose
Sucrose is made by the joining of 1 molecule of ... and 1 molecule of ...
130
fastest
Tertiary halides undergo elimination the
131
most substituted; least substituted *BLAM (Base is Less; Acid is More)
The addition of an acid following Epoxidation, would allow it to attach at the ... carbon. Whereas the addition of a base would allow attachment at the ... carbon.
132
base, hydrogen, an acidic proton; an acidic alpha proton.
The Grignard is a powerful ..., it will remove a ... from any compound with ... If something lacks ... Grignard will not react with it.
133
*Carbonyl CO, an amine *Hoffman rearrangement uses Br2/OH- reagent
The Hoffman rearrangement occurs where a primary amide lost a ... and became ...
134
Alcohols: 3300 Ketones: 1720 Ethers: 1100 Carboxylic Acids: 1720 Aldehydes: 2800 Ammines: 3100-3500
The IR spectroscopy frquencies for Alcohols, Ethers, Aldehydes, Ketones, Carboxylic Acids, Ammines are ... (cm^-1)
135
conjugated (double bonds like in benzene); longer e.g. Anthracene is made of 3 rings, it is most conjugated and has the longest wavelength in UV
The more ... a molecule is, the more stable, more likely to have color, and the ... will be the UV wavelength absorption.
136
lower, higher, decreased surface area
The more branched the substance, the ... the boiling point, and the ... the vapor pressure, due to ...
137
an Aldehyde. *Remember NaBH4 is a mild reducing agent an only reacts with aldehydes and ketones, it will not reduce esthers or carboxy acids.
The only molecule that can be both oxidized by K2Cr2O7 and reduced by LiAlH4 or NaBH4 is
138
halide and the nucleophile, 2nd order kinetics
The rate for SN2 reactions depends on the ... the rate is ... order kinetics
139
halide, it is nucleophile independent
The rate in SN1 reactions depends on the
140
Keto-Enol Tautomerization (alcohol becomes a ketone)
The reagent HgSO4, H2SO4 and H2O is
141
replaces an acidic proton or OH- group with OTs
The reagent TsCl, Pyr ...
142
100% inversion of the chirality center (100% R or S)
The SN2 stereochemical result is ...
143
Ether; in a solvolysis reaction, the solvent acts as the nucleophile. Here a tertiary halide (t-butyliodide) is involved in an SN1 reaction.
The solvolysis of t-butyliodide in ethanol will produce
144
inversion, racemization
The stereochemical outcome of SN1 is partial ... and partial ...
145
Cellulose, Starch, Glycogen
The structural component of plants is ..., ... is the storage component of energy in plants, whereas ... stores energy in animals.
146
an SN2, small, unhindered, primary methyl halides.
The Williamson Ether Synthesis is ... type of reaction. It works best with ... halides.
147
Cellulose, Starch and Glycogen
Three most important Biological Polysaccharides are
148
use a base such as NaOH
To extract a phenol...
149
use a base such as NaOH or NaHCO3
To extract an acid...
150
use an acid such as HBr
To extract an amine...
151
evaporation of the ether
Toluene that is suspended in an ether layer of solution can be removed by
152
greater strength, greater
Triple bonds have ... than double bonds, thus they vibrate at a ... frequency.
153
True
True or False: An aldehyde can be oxidized into a carboxy acid if simply exposed to air
154
True, know this
True or False: In nucleophilic acyl substitution the reactivity is Acyl halide > anhydride > thioester > amide > ether
155
True; all of these are lab techniques needed to separate organic compounds
True or False: Organic compounds can be seperated by techniques such as extraction, recrystallization, distillation, thin-layer chromatography, and gas chromatography.
156
True
True or False: Saturated fatty acid tails pack very tightly together, giving a triglyceride with a high melting point, and solid or semi solid appearance.
157
False, the least polar molecules elute first, everything else is True
True or False: The correct order of polarities of solutes in colum chromatography is alkanes> alkenes> ethers> esters> aldehydes> ketones> alcohols> acids; The most polar elute first.
158
2 NH stretches; an amide, CO carbonyl stretch, though it is usually found at 1720, the amide has resonance so the stretch will be slightly less.
Two bands near 3200 and 3400 cm^-1 represent ... stretches. If there is also a band at 1670 cm^-1 it means there is a ...
159
fewer, lower
Unsaturated fatty acids have ... intermolecular attractions and have ... melting points than saturated fatty acids.
160
excited, promoted into higher energy levels; conjugated molecules
UV spectroscopy examines transitions between electronic energy levels, meaning electrons become ... and are ... This is only done for ...
161
not permitted
When a molecule contains double bond character between two atoms, free rotation is ...
162
quickly, less, more quickly
When choosing the most acidic proton, sterics must also be taken into consideration because acid-base reactions occur ..., thus the ... sterically hindered proton will be removed ...
163
2^N rule; entantiomers for meso compounds
When figuring out how many stereoisomers can be written, we use ... rule and disregard the ...
164
Mutarotation
When Glycosidic reactions form beta and alpha acetals in equal amounts this is called
165
a carbonyl and an alcohol OH- group, respectively
When looking at an IR graph we see peaks at 1720 cm^-1 and at 3480 cm^-1. These numbers indicate the presence of
166
an Aldol Condensation; loss of an OH- group, forming a double bond.
When NaOH and H2O act as reagents this indicates ... The additon of Heat causes ...
167
the benzylic position; 1 carbon away from the benzene ring
When NBS reacts with benzene, a Br group is attached to
168
opposite directions e.g. (S)= +3.8 degrees, (R)= -3.8 degrees, two different values, polarimeter
When two molecules are enantiomers, they rotate light in ..., and show ... for their specific rotations when placed inside a ...
169
decarboxlyation
When you have a Beta-keto acid and heat is added ... occurs
170
Sulfonation, just add heat
Which electrophillic substitution reaction is reversible?
171
Ester, (-COOR)
Which is a carboxy acid (-COOH) derived molecule?
172
b) 2-pentanol; lowest vapor pressure=highest boiling point, since alcohols contain H-bonding they have very high boiling points.
Which of the compounds has the lowest vapor pressure? a) 2-pentanone b) 2-pentanol c) Pentane d) Pentanal e) Hexane
173
an SN2 reaction, primary or methyl halides work best, it reacts with an alkoxide
Williamson Ether Synthesis is a .... reaction, the halide must be ... or ..., and the reacting molecule an ...
